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How can I get over feeling I'm too old to have a girlfriend at 26? How should I flirt, talk to and approach women?

Tagged as: Big Questions, Dating, Friends, Troubled relationships, Trust issues, Virginity<< Previous question   Next question >>
Question - (23 December 2014) 38 Answers - (Newest, 15 May 2015)
A male United States age 36-40, anonymous writes:

The fact i'll be 27 in a few weeks and I still haven't had a girlfriend yet, obviously still a virgin, the fact that I didn't have my first girlfriend and didn't lose my virginity around the age-range most people do just makes me bitter and frustrated all the time.

I'm going to have to live with for this rest of my life, whenever people say better late than never or it is never too late, you have plenty of time.

It just angers me and annoys me whenever people say that, and I remember it also annoyed me ven more, angered me even more when a woman tried to give me reassurance by telling me I should feel lucky for being born a man.

Man as in human male, because I don't have a biological clock.

In fact i'm kind of jealous and envious of women more so than I am of men who are successful with women, because when women are young, in their late teens and throughout their 20's, some extent early 30's, which are womens peak fertile child-bearing years, women have loads and tons of options for dating, means that it is an almost for certain guarantee that women will not miss out on their youth.

If a man wants to prevent himself from missing out on his youth, he better be hardcore assertive and go out a lot, be putting himself out there often and consistently, have good social skills and conversation-skills, good confidence and self-esteem, a big social circle.

Women are generally on the receiving end of sexual attention, requests for dating and relationships while men are on the projecting end. It is easier for a woman to date more than men, because as long as she is willing to date among the men that approach her, she can date.

A man must pursue, initiate, escalate, and if he has any negative experiences that deter him, or if he is just very very shy, socially-awkward he could end up an adult male virgin very easily. The irony is that the older he gets, the more women refuse to give him a chance because of his inexperience.

I just never know how to approach and talk to women, flirt with them, etc. It was never common sense for me.

I don't care if men don't have the biological clock that women do, because I didn't start when most people do it makes me unmotivated to take action to fix my issues with women.

View related questions: confidence, flirt, jealous, shy, still a virgin

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A female reader, eyeswideopen United States +, writes (15 May 2015):

eyeswideopen agony auntYes the I'm afraid the boat has sailed for you. You are now just swimming around in the sea of misery and self-pity. I hope you are a good swimmer cause I don't envision you reaching dry ground for quite awhile.

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A male reader, BrownWolf Canada +, writes (15 May 2015):

BrownWolf agony aunt"I want to experience a couple of break-ups, drama, even if it means getting cheated on, before i'm ready to get married and settle down."

Folks this is the truth about the saying "Misery loves company".

Here you are already depressed and swimming it it...but you don't want to get out..you want to experience break-ups, drama, and being cheated on. You want to be stuck in your own misery...wow.

Sad part is...you never said you wanted to find love...just all the negative things.

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A female reader, chigirl Norway +, writes (15 May 2015):

chigirl agony auntWho says you need to get married?? I so do not follow your logic, it makes no sense. How to avoid marriage; dont propose and dont say yes if proposed to. Easy.

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A reader, anonymous, writes (15 May 2015):

This is verified as being by the original poster of the question

When you said: "Young people are foolish when it comes to relationship, dating, sex, love, emotions, and all that stuff.

It takes most people into their 30's to figure out just what they want from the opposite sex in order to settle down. Some even longer."

"Young people are driven by lust, and how they feel. I feel sad, I feel depressed, I feel horny...and they all want the quick fix. They have no idea about the work needed to fix their problems...nor do they care to try."

Sounds like the boat sailed long ago, I missed out on immature dating and relationships, that i'm too old for casual dating, I don't want my first girlfriend to become my wife, I don't want to settle down or get married to my first, I want to experience a couple of break-ups, drama, even if it means getting cheated on, before i'm ready to get married and settle down.

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A female reader, CindyCares Italy +, writes (14 May 2015):

CindyCares agony aunt I am glad that you and I did not get the same memo and we did not read the same books. Otherwise, I would not have enjoyed relationships- and sex too - as I did in my 40s and 50s.

Oh so it's all stuff for the youngsters and then no more ?...

Uhm, no, I do not get this impression from the tons of letters I have read by now on DC. Nor, actually, just from living my life normally, out there, among regular people who struggle and fail in love, and try again, and has good times and bad times, and find love and then lose it and then find it again - people who is not too busy building up ( harebrained ) theories , and moaning about their bad luck, to forget ...just living, at any age, with relationships and all.

OP ! Don't you realized that what you wrote is , well, sorry, ridicolous ? Supposing rhat society actually said that love is only for teens and 20somethings- well, f..k society then ! . Sex and love , and the wish for them, are just a part of human experience, and, believe it or not, we all are still human at 50, 60 and beyond. It 's like saying that food is only for young people, or books , or music. Absurd. Of course it won't be the same food, or books, or music; they will be different, consumed in different quantities and in a different way or shape or attitude,- but that's hardly surprisisng is it ?

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A male reader, BrownWolf Canada +, writes (14 May 2015):

BrownWolf agony auntWHOA!!! Hold up there!!! Young people are foolish when it comes to relationship, dating, sex, love, emotions, and all that stuff.

It takes most people into their 30's to figure out just what they want from the opposite sex in order to settle down. Some even longer.

Young people...Please... If I met my "younger" self, I would reach back all the way to the North pole, and slap myself so hard for being stupid. Thank GOD I learned before it was to late.

Young people are driven by lust, and how they feel. I feel sad, I feel depressed, I feel horny...and they all want the quick fix. They have no idea about the work needed to fix their problems...nor do they care to try.

As you get older and learn that you have to be the one to fix your own life, common sense starts to kick in. That is why the older you get, the wiser you should become...because you have learn to have common sense...hopefully.

Some of us refuse to let go of our past and drag it around like a big heavy stone. A big stone of sadness, depression, guilt, envy, broken dreams, things and people you have lost, and a Sh*t load of "what if's" or "I should have's".

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A female reader, chigirl Norway +, writes (14 May 2015):

chigirl agony auntYeah, you keep wondering...

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A reader, anonymous, writes (13 May 2015):

This is verified as being by the original poster of the question

I often wonder, why do people bother and still continue having relationships, dating, sex, in their 30's and beyond when dating and relationships, sex, is still primarily something that young people do, teens and 20-something people do? all of our culture, the media, society, emphasizes and potrays that dating, relationships, sex as something that young people mostly do, as in teens and 20's, it irritated me when someone said to me:

"realize that plenty of people are still looking for love in their 50s. Sure, they might not be virgins or inexperienced, but being older has not stopped them."

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A female reader, maverick494 United States +, writes (10 May 2015):

If you want a better life, you're going to have to take some risks and make yourself vulnerable.

Your life as it now is going to be your future if you keep your current attitude. Doing the same things will give you the same results.

So take a chance and don't be so afraid of rejection. So what if that happens? I took a chance on a guy two weeks ago. I met him a few months ago, liked him and I gathered my courage and asked him out. He unfortunately didn't like me back that way, but I'm happy I tried. Because if I hadn't I'd have been stuck with that question of "what if" in my head and I want to have as few of those in my life as possible.

Stop being so damn afraid of getting hurt because this attitude of yours is doing so much more damage than any person can do to you. Your biggest obstacle to overcome is yourself.

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A reader, anonymous, writes (10 May 2015):

This is verified as being by the original poster of the question

I actually am behind most people, most people lose their virginity, experience their first relationship before age 25, i'm past that age now.

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A female reader, CindyCares Italy +, writes (10 May 2015):

CindyCares agony aunt And ?... Do you expect to be the only human being who's spared any pain and frustration in their life ?...

Are you entitled to feel only happy, positive emotions ?

Pain and frustration at some point belong to everybody's life. Some people are frustrated about not getting a job, or not getting pregnant, or not making enough money, or not having enough friends... - everyone has got some fly in the ointment ( when there's an ointment at all ! ).

You just play the best you can with the hand of cards you have been dealt with, without expecting / demanding that life NEVER has to feel challenging / difficult / frustrating for you. Which, pardon me, but is a childish attitude . In a way, it's a good thing that you can't find a partner until you have found a more mature way you deal with your emotions ,and raised your level of, well, courage - otherwise any r/ship you might have would last , like, 5 minutes anyway.

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A female reader, chigirl Norway +, writes (10 May 2015):

chigirl agony auntYoure not behind anyone, that is just something you tell yourself. Everyone else your age are just as far in life as you are. Different experiences does not mean anyone is further ahead or behind. Allow yourself to live some. You only have one life. Why waste time being resentful when you can go out and enjoy life? If you struggle with letting this go, then you should talk to a therapist. It helps.

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A reader, anonymous, writes (9 May 2015):

This is verified as being by the original poster of the question

well the fact i'm starting late and theres nothing I can do to make myself younger again, that i'm way behind everyone else is painful, frustrating for me.

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A female reader, chigirl Norway +, writes (9 May 2015):

chigirl agony auntThat is a strange logic. In order to not feel pain of having "missed out", you will not allow yourself to experience anything at all. How does that do you any good? Then you can be 40 and a virgin and look back wondering why you, at 26, were denying yourself the experiences.

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A reader, anonymous, writes (8 May 2015):

This is verified as being by the original poster of the question

the reason why at times I often feel unmotivated to take action to fix my issues with women, is because I feel if I ever do get a girlfriend and start having the dating life/sex life I always wanted, I will never be able to heal the mental and emotional wounds, scarring, pain of missing out the years when I was younger, like when i'm out there in public and I see all these other couples younger than me, it will be a painful reminder of what I missed out on earlier and will never get back.

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A female reader, anonymous, writes (16 January 2015):

I understand what your feeling beileve me! I'm 22 and a virgin, and I've been feeling the same lately.

It's very easy to see the happy couples on Facebook or in the street and be annoyed that you don't have that, or that your behind everyone else, but the fact is what were not seeing is the big picture.

We are not seeing the fight that couple had last night etc

As for the women thing, I'm 22, a women and I've never had a boyfriend, it is not easy for women, we can feel exactly the same.

Have you tried online dating? Even if nothing comes of it, it could help with confidence, I've used it for a while and as slowly changed how I act around men.

You need to relax and enjoy yourself, you will find the right women when the time comes.

X

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A female reader, chigirl Norway +, writes (28 December 2014):

chigirl agony auntAh, your latest update makes me think you started your post on the wrong foot. This doesn't really sound like it's about being a "late bloomer" at all. Sounds to me like you're generally frustrated about where your life is heading, or more than you feel you're not heading anywhere at all.

I know you might find this hard to believe, but you are NOT alone in feeling like everyone is 5 steps ahead of you, and everyone else have their life in order and got things going for them. It's mainly a facebook thing, I think. One look on facebook, and you are made to believe everyone else are living the most amazing and successful lives. At times when you don't feel like you've got a lot going on for yourself, it can be depressing to see everyone else show off like that. But trust me, it's not true at all. Everyone else have things in life just the same as you do. Maybe they have a steady job, but it might be a low paying job they hate. Maybe they have a place of their own, but are ruining themselves financially because of it. Maybe they have rats or mice... Or the basement is flooded. You just never know these things, but they might be sitting there envious of you, who are at home and saving money. Or envious of your opportunities. Many people I know of, especially who got kids early on, end up feeling trapped and stuck in a place they don't want to be. Not that they regret their kids, they love their kids... But career wise they are trapped, because you cant just up and leave for new opportunities when you have kids. They can't just up and leave if a new exciting job opportunity presents itself. And they will envy you that freedom, just like you envy them that state of being established.

You will see this, eventually, but right now you're so deeply focused on what you term your own misery, that you can't see that you are no more miserable than anyone else in life. They have what you don't have, and you have what they in return don't have. It's a two way street.

And, in time, you will also realize that this is not at all a gender thing. There are so many women out there who feel like they are missing out as well, that it's not even funny. Just here the other day a friend of mine (age 30) was wondering when she'll meet her special someone, after being single for several years. People who are looking for a partner are all around you, just right now you're so focused on being miserable by yourself you can't see them. All you can see are the ones who confirm you "misery": you see couples everywhere. You see successful people everywhere. But it's a matter of what you're focusing on.

Whenever I feel down about not having gotten married with kids already (when I was a child I thought I'd be married with kids waaaaaay sooner, and as such sometimes feel like Im "too late" in life), I just think of a friend of mine. My friend got pregnant at 18, never finished high school. She had kid number two shortly after the first, so never had a job, was just home with the kids. Eventually married the father of her children. But later told me she knew he wasn't right for her, and didn't want to marry him, but all the preparations were done, and she felt obliged to do it. Then she finally got a part time job flipping hamburgers, and cheated with a coworker. Got pregnant with her third child, and still doesn't know who the dad is. Never told her husband. Wanted a divorce, but can't afford her own place due to no education, no job. They bought a house together, but it requires a LOT of renovation, and is in poor state.

On the outside, on facebook etc. there can only be found lovely wedding photos, bragging about how the new bathroom is finally finished and now looks so great, how the kids are doing and how cute they are. On the outside, it looks like she's got it all, and she doesn't hesitate with telling everyone how happy she is, and how happy she is about having had kids young, how it's best for the kids etc. Just to make everyone else feel bad about not having a husband, house and kids already. But I know the truth. And I am glad I didn't end up in her situation, and I'd gladly be a "late bloomer" if it means avoiding ending up like her.

So trust me. Everyone else doesn't have it all. You haven't missed out. Everyone has some shit they are going through, some secret they don't want others to know about, something that ruins the "perfect picture" of their life. Do yourself a favor and remember this whenever you see someone who's seemingly perfect and successful.

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A female reader, maverick494 United States +, writes (28 December 2014):

OP, don't forget that most of age related milestones have a direct correlation with money and/or luck. Things that a lot of people don't have in this economic crisis. If one wants to college, they need money. If they want to live on their own, they need money. If they get a degree, there's no guarantee of a job. A lot of companies only hire underpaid interns (if they get paid at all). Etc. This is something a lot of people struggle with.

Trust me when I say you're not the only one over 25 who doesn't have a career yet and hasn't moved out of their house yet. And if younger and/or older people condemn you for it, it's just because they're ignorant. Don't mind them.

Please just don't paralyze yourself by getting hung up on your age. Thinking about how much better things would be if you could be 20 again (or whatever age you deem 'acceptable') with the knowledge you have now is very dangerous. You can get stuck in it and time will still tick by and then when you're older you'll think: why didn't I grab my chances at 27?

I spent the first half of my twenties feeling old and miserable. Now I look back on it and shake my head at all the time I wasted. That's 5 years I could have filled with better things and I can't get it back. I don't dwell on it though because it taught me a valuable lesson. Don't spend today hating the you of yesterday.

Think: all these things that happened and didn't happen made me into the person I am today, for better or worse. When I was younger, when my family didn't have financial problems and a lot of things didn't cost me much effort, I looked down on people who had a hard time getting their life on track. Now I know better. I have a lot more compassion and understanding for people than I used to. I think that if I'd been successful all the time, I would not have gained this understanding. Failure teaches you humility and that's a very good thing.

And you know, perfect people are boring. Who wants to see a movie or read a book about someone who got everything right in the first try? That's not relatable to anybody. People want to read about and see characters who fail, who fuck up, who hit rock bottom, but crawl their way back up again. Every human being fails at things.

You feel being a virgin is a failure. Well, look on the other side of the coin: being the person who had sex at an "acceptable" age but got an STD because they weren't careful. People do or don't do stuff they regret all the time. All you can do is your best to deal with the consequences.

Also, please don't make the mistake of waiting until you have your career sorted out before you take a chance on a relationship. If you encounter someone interesting, just go for it and let the chips fall where they may. If the relationship and your career path don't mix and the relationship ends, well at least you got to experience it. You get to really know people when things aren't perfect for them, in a way you don't when everything is going right.

Stop beating yourself up with should've's, could've's and if only's. I know I've been harsh on you but I really don't want you to spend more time in this destructive cycle. Life isn't a competition. Who gives a shit at what age you do this or that. Just make sure, you do the things you want to do at some point in life.

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A reader, anonymous, writes (27 December 2014):

This is verified as being by the original poster of the question

Overall, the deep root of my anger, rage and frustration is the pain of being a late bloomer and the fact I will never get my past years back, it's nobody elses responsibility but my own, since i'm a guy i'm expected to be responsible for everything, and the fact that i'm still trying to discover my career path, don't have a career yet, although I do have a job, it's just i'm not financially stable yet, live with my parents, i'm also worried I might have to put dating off for a long time until I get this area of my life sorted out and i'm not getting any younger either

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A female reader, Euphoric29 Germany +, writes (26 December 2014):

Dear OP,

Who else can fix your issues, if not you?

What I can do from my part is to send you some positive, female energy through the internet. I wish for you that this new year will heal you, give you new and better experiences. I wish for you that you can experience that women are just human beings, not a different species from you, that can understand you as a fellow human. I wish that you can experience that a woman can forgive your weaknesses, love you for your honesty, embrace you with your mistakes and imperfection. I wish for you to experience the tenderness that there can be between two people who have healed from their past, who can embrace again with faith and hope.

I believe that in order for this to happen, you must start your own journey of healing. I had my troubles with men for a very long time. I never had sex with a man until I was 27, because I was full of fear and hatred. And from starting to have sex with men to experience true love with a man, it took me 4 more years. I can tell you, it was painful to face my fears, face rejection, face coercion, face dissapointment. It was a journey where I was scared that it would all turn out worse than when I started. But to be able to feel love without scepticism, feeling deep trust and peace again, was worth it. I'm still very sad, because I lost the love I found, again. But the inner process that I made, has made me rich.

I'm not saying "good things happen to those who wait". Nothing happens to those who passively wait and complain. But so many things are possible, if you're willing to make an effort.

(By the way, just as a reminder: Some women just don't get pursued by men, because they don't conform to societys standards of beauty.. the coin always has two sides, my friend, and loneliness isn't a male privilege)

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A female reader, maverick494 United States +, writes (26 December 2014):

"the way I see it, men have to earn a date, a relationship more than women do, since men have to be the pursuers."

Okay, so based on that info you have two options:

#1. Roll with it and pursue women that interest you until find someone who likes you back.

#2. Whine about how unfair life is and not do anything at all, which hasn't gotten you any results in the past 10+ years.

Look, you can't just wait around for the world to change for you, because it won't. You have to make do with what you have. That's just the way it is, for everybody. People who delay their actions 'until the time is right' are likely still waiting for that perfect moment. Newsflash, it'll never come.

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A male reader, CMMP United States +, writes (25 December 2014):

Okay, let's say you're right, because you probably are. It's also not a big deal to leave your comfort zone and ask a girl out.

And socially awkward women may get asked out more than socially awkward men do, but they probably have a pretty hard time getting asked out on a second date.

Get over your fears. A TON of people are afraid to ask someone out. What's the worst that could happen? They'll say no. But what if they say yes? It could change your entire life. And let me tell you if ten women say no to you before one says yes you'll forget the first ten even exist.

Or, stay safe. Look where it's got you so far... You just have to ignore your fears and do it... Be brave.

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A reader, anonymous, writes (25 December 2014):

This is verified as being by the original poster of the question

the way I see it, men have to earn a date, a relationship more than women do, since men have to be the pursuers.

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A female reader, maverick494 United States +, writes (24 December 2014):

But OP, what has all this bitterness and negativity brought you? I'll answer that for you: it brought you safety because if you can blame it on those abstract things instead of yourself, then it's not your fault. And that is exactly the reason why you're a 27 year-old virgin. Look, if you want that to change, YOU have to change. You can't go back and say "but if only I had known this and that when I was younger, then none of this would be an issue."

The thing is, when you were twenty you were probably held back by the same bad attitude. It just got worse over time as you grew more resentful over getting older and not ticking a box. When people say it's not too late, they're right. The only problem is that for something to change, YOU have to change. You can't expect a different outcome with the same attitude.

The past is generally a good indication of the future and if you keep stewing and brooding over how these gender roles are keeping you from dating, you'll be stuck in the same situation ten years from now. Gender roles are not keeping you from being with someone. YOU are. You're sabotaging yourself and unless you start seeing that you're going to be single for a long, long time.

Look, I'm 26 and I'd have absolutely no problem dating a 27-year old virgin. Your virginal status means absolutely nothing to me. It's actually kinda nice not having to deal with a slew of exes or a guy bragging about how many girls he banged in his lifetime. That said, the way you cling to gender roles would definitely be a problem, because it tells me you have a habit of blaming circumstances for your own shortcomings and that's a very bad personality trait.

Do with this what you want, but you have to be honest with yourself why you came here for advice. Was it for confirmation of your ideas or because you actually want to know how to change your situation?

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A reader, anonymous, writes (24 December 2014):

Hey this is the first guy who posted. I was expecting some female hate, it was begging for it, but you need to calm down and take a look at yourself here man. Why are you so angry? It really isn't anyones fault but your own you are where you are, ignore the straight hate posts for a second. Iv'e been where youv'e been, granted i was younger and feeling the same but it was chalked up to my initiative, low self asteem and well, pure laziness.

No a woman probably isn't going to just walk up and plop herself on you, but neither does a guy. I remember wishing a girl would initiate first because i thought i was incapable, too ugly, too fat etc. When in fact looking back now i can see that a few girls i knew probably DID initiate but i was so focused on my own self pity i couldn't see it. I was angry at the world for not just giving me what i wanted, like anything else you have to work towards it.

You don't just begin a career without earning it, you don't finish degrees or school without effort. Well you don't enter a relationship without earning it, and be mad all you want, but it isnt too late. On a scale of life your not even close to half done, and only you can change it. If you need professional help, or some type of guidence, seek it out to get to the next level. I don't know your situation or what in your mind is disabling you from socializing with women but focus on what that is. Get around it and try and get some self confidence!

The thing i notice most is your very negative in general, in your second post its just more negative. Rather than taking the good information your just tossing it and attacking the negative. If all you see is negative, it will be all you feel and live. Try and focus more on the positives in your life. Who are you close to? Are you good at what you do, at your hobbys? The people in your life right now, and your aspirations for life. Lifes too short to be angry over things you cannot change my man.

Hope you can figure things out, there is hope, there is a way and your never stuck where you are

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A female reader, anonymous, writes (24 December 2014):

Taking your anger out on how jealous you are of women won't help you. Most women will see right to that and it already ruins your chances.

Having such an angry, negative mentality just keeps your right where you are and it's hard to feel sorry for you when you have such screwed up ideas on gender roles in society.

Take note of the good advice here, I don't need to repeat it all. You need to LEARN about women and you need to RESPECT a woman before she is going to allow you to share her company.

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A female reader, anonymous, writes (24 December 2014):

"pissed off because I didn't start around the age most people do, if I knew how to initiate, escalate and approach, talk to women in my teens and early 20's in which it resulted in success with women, then I would not be resentful over this gender role."

That's your own fault. Sure, traditional gender norms do set expectations when it comes to dating and pursuing relationships with the opposite or same sex, but we've come a long way from the 1950s.

You not starting at the "age most people do" is of your own volition (or something else which you are not sharing). I don't get what gender roles have to do with your inactivity. If anything, according to your view about women being on the receiving end and men being the aggressor pursuers, it should have pushed you to "initiate, escalate and approach, talk to women" in your teens and early twenties.

"in which it resulted in success with women"

And if your adolescent and early twenty years ended with no success? Would you be on here complaining about how women don't give you a chance after you put in so much effort to approach them and ask them out?

All this bitter, entitled nonsense you're spouting is very alarming. You should see a counselor and it's probably in your best interest to get off the Internet.

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A reader, anonymous, writes (24 December 2014):

This is verified as being by the original poster of the question

it pisses me off whenever people say it is not a race, you have plenty off time, it is never too late, it makes me angry and mad, pissed off because I didn't start around the age most people do, if I knew how to initiate, escalate and approach, talk to women in my teens and early 20's in which it resulted in success with women, then I would not be resentful over this gender role.

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A female reader, ConfusedButInLove United Kingdom +, writes (23 December 2014):

I do not disagree with you, women do get more attention... I think you just need to be yourself, go up to a pretty lady, and smile, say "hey". Ask if she wants to go for a drink maybe? Just play it cool, be confident, and smile, smile, smile!! Behave like a gentleman and once again, smile, smile smile! A simple smile is a charmer! :)

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A female reader, Honeypie United States +, writes (23 December 2014):

Honeypie agony auntIt's not your age that is holding you back from a fulfilling relationship, it's your attitude and how you generally view women.

I have no idea HOW ON EARTH you have come up with this absurd and skewered view of women VERSUS men, but it's absolutely flawed. This isn't about gender. This is about you having a odd sense of entitlement. NO ONE is entitled to a BF/GF. Most people DO have one at some point in life, but the reason most people HAVE/HAVE HAD one (pr more) is because they PUT THEMSELVES out there.

I have pursued guys, I have been rejected. I have been pursued and I have rejected some.

My advice STOP seeing women and sex as some kind of trophy. IMPROVE your social skills. LEARN to interact with people, not just women, guys too.

YOU can do it. But it's up to you. NO ONE is going to do life for you. But it starts with losing that attitude and actually taking steps to get to know other people. Women included.

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A female reader, anonymous, writes (23 December 2014):

Some good advice here, OP. You should take it or return to r/foreveralone where all they do is complain about how much women have it easier, they slut around in their 20s because they have so many options and is on the receiving end, and men are undervalued even though they're the ones who have to make the effort.

Get over your assumptions ofrelationships, which you essentially reduce to a market place, and realize that plenty of people are still looking for love in their 50s. Sure, they might not be virgins or inexperienced, but being older has not stopped them.

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A female reader, chigirl Norway +, writes (23 December 2014):

chigirl agony auntIt annoys me a lot when men like you make stupid assumptions about how women have loads of options while they, as male, as to be pitied because they don't have options to get laid.

It's all crap and a self fulfilling hypothesis of yours that enables you to continue throwing yourself a pity party. Fine, you don't like being a virgin at 27. Poor you? Sure, I can say poor you, I get that it makes you feel miserable and envious of others who are in relationships. I'd feel that way too. But back off from throwing shit and generalized assumptions about women. We do NOT have so many "options" as you call it, not any more than men do, and there are actually women your age and older who haven't ever had a relationship/sex either, so just drop that idea of "women having it easier".

If you're really going to continue wallowing in pity because you think it's unfair that you don't get approached like women do, I suggest you visit a gay bar and put yourself on the "receiving end", as you call it. Get approached, see if you get picked up on and chatted with. Maybe it'll make your feel better about yourself. But just be prepared, just because one is on "the receiving end", doesn't mean you are guaranteed to actually GET anyones attention.

And for the sake of the argument I will remind you that while women traditionally have been the ones to be chatted up by men, not all women get approached by ANY men. Also, women in this scenario can not choose who they want, but will have to settle with whomever comes along. As most modern women do not like to settle with whomever choose her, but would like to be an active part in a relationship as well (as opposed to just an item that is chosen, like if we were an object in a super market), they will want to choose themselves. So women DO initiate contact, flirt, and take an active part in picking the guys they want. I don't know a single (as in, one) friend of mine who was NOT an active part in pursuing their relationship.

So do me a favour, pity yourself all you want, but let go of the notion that women are brainless objects that just stand around waiting to get picked up and who spread their legs for whomever comes along. Oh and do also drop the notion that women are only good for receiving attention when they "are young, in their late teens and throughout their 20's, some extent early 30's".

Women have to put themselves out there just as much as men do, so drop the act. I know this to be true because of my own personal experience, both with pursuing men and women (I am bisexual), and from what I've seen around me.

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A male reader, anonymous, writes (23 December 2014):

In your post you seem to know everything about men and women relations so why can't you put your knowledge into practice and go out and pursue women. They are not going to kill you if you approach them nicely.The worst they can do to you is say no thank you. Also maybe you are searching only for that perfect and ravishing beauty to date. It doesn't work that way. To get that ravishing beauty you have to have a lot of previous experience with girls. So start with ordinary looking girls who would bear your inexperience. I agree with all the other answers. They are sound advice you should head to.Go for it.

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A male reader, CMMP United States +, writes (23 December 2014):

There have been plenty of women posting similar questions here. Don't act like you have it all figured out because it's convincing you that you're done for when you're not.

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A female reader, maverick494 United States +, writes (23 December 2014):

The first thing you need to get past is this whole "men versus women" thing you've got going on. The societal pressure is toxic for everyone and men and women's issues are interconnected.

To illustrate this, look at the average Venus and Gillette shaving commercials, which perfectly show what society thinks men and women should be like.

- Women are depicted as flawless skinned permanently youthful goddesses trying to look innocent and sexy in a body that's at such a low weight it'll never be strong. She'll never raise her voice, only speaking in breathy, soft cadences. Her interests are only superficial: she values beauty and money.

- Now, the guys are shown off doing dude sports like mountainbiking, skydiving, free climbing. The man is aggressive and strong, he's an animal, rawr, he's mature; at that age where you can't tell whether he's 30 or 40. His razor is black and called Mach something, because anything else makes it feminine and feminine things are weak and men cannot be weak.

Do you see where I'm going with this? Because women are weak and meek, men have to be strong and aggressive. Women can't have many sexual partners, or she'll be a slut, which of course means that men have to basically behave like they think with their dick because 'real men' only think about sex. Etc. etc. This leads to bad situations, like for example the one were a woman's worst nightmare is getting raped and murdered by a guy on a first date and a guy's worst nightmare is a woman laughing at his advances. God forbid you're trans or something else.

Bottom line: society is messed up and no-one in their right mind should use it as a guideline. It's built on marketing and politics and ulterior motives and therefore only serves to make people feel miserable and inadequate.

This is why more and more people are starting to stand up against that so they can try and change these damaging views that somehow have become mainstream. You, on the other hand, have let all this BS invade and poison your brain and now you blame it for your virginity. Virginity is a social construct. You've built it up in your head as this huge wall that's gotta be brought down, but honestly, nothing really changes after you've had sex for the first time. The only thing that's changed is in your head. And one of the first things you'll probably think is: "Why the hell did I make such a big deal out of this?"

But before we get to the sex part, we need to get to part where you get a girlfriend. And man, if you keep viewing women as adversaries that are deliberately keeping you from achieving your goals, you'll stay single forever.

Get rid of all this baggage society has heaped upon you and accept that you don't really know a lot about women at all. And that's fine. That's a perfect starting point actually, because once you admit you don't know something, you can really learn and familiarize yourself for once.

And you'll find woman are not so different from men. Their desires are not really different from yours. Talk to them like you would talk to anybody. As for flirting, flirting comes naturally when you start feeling comfortable in your own skin. That's when you start making more eyecontact and that's what flirting is all about: showing an interest.

Make a habit of talking to different people every day. Study their body language. Once you get past the anxiety of having to keep up a convo, you'll find you can do that anywhere. And you'll learn to pick up cues too. Don't be afraid of silences. They don't always need to be filled up. Don't be afraid to not know something; turn the tables, maybe she knows. And lastly: NEVER assume. That's where people do the most damage. They assume negative stuff about others and they're wrong.

When you get to your first time, if you're really anxious about your virginity and all the social baggage, don't mention it at all. Just follow her lead and communicate: ask for feedback on what she likes and tell her that you want to give her a good time. Every body is different after all.

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A female reader, anonymous, writes (23 December 2014):

When I was a teenager, even my freshman year of college I was terrible with boys. I was so shy. Fortunately, college taught me a valuable lesson: practice makes perfect. If there was something I didn't know or wasn't good at, I didn't sit there kicking dirt, like you do. I took on the challenge and learned about the subject and kept taking a shot at it and practicing the skill I was no good at until I was good at it. I was a terrible writer when I started college. So I took a lot of writing classes to learn. Then I started getting compliments on how good I got.

When I started college I was a blank canvas. In college, I learned to play the guitar, I learned a third language, I learned to ski, to paint with oils, I learned kickboxing and yoga, I learned to dance, I learned to pay bills, do my taxes, learned to cook.

And I learned to date. Like you, I had no clue how to date or how to get a guy to like me. But I took on the challenge. I put myself out there, made a lot of mistakes, got rejected. I didn't care, I took it as a learning experience. I tried and failed and tried again and did it enough times that I became a pro. It eventually became easy for me to get a date, and to be likeable and be good company, I gained an understanding of men. How they think, what they like.

Just get out there and start talking to girls, get to know them, see what they like. Ask them out to dinner. Be objective. Observe yourself and think about what you could do better or do differently. And learn.

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A male reader, BrownWolf Canada +, writes (23 December 2014):

BrownWolf agony aunt

Are you okay??? Your mind has gone to the North, South, East, and West poles... WHAT!!! Who on GOD's green Earth gave you all this information??

There is one sure way to pick up any and all women...100% for sure...Ready?!?!? Okay here goes... "Hi" SSSSHHHHH!!! That is top secret stuff. Wait...there is more..."Hi, my name is... What is yours??" Oh man I can believe I am telling you this. Most women would kill me if they knew I just gave you this info...Damn!!!

Want to keep a woman??? First thing you have to do is...get rid of "It just angers me and annoys me" And... "i'm kind of jealous and envious of women" And all this crap ...

"A man must pursue, initiate, escalate, and if he has any negative experiences that deter him, or if he is just very very shy, socially-awkward he could end up an adult male virgin very easily. The irony is that the older he gets, the more women refuse to give him a chance because of his inexperience."

Women are human...not toys or animals. You love them..hear me... LOVE THEM...and they will love you back. What you plant you will harvest. Get me???

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A reader, anonymous, writes (23 December 2014):

First off, have you looked into dating sites? They are tailored to help out guys (and girls) with social anxiety find eachother! Not ALL women are blessed as you think they are. I know a 25 year old girl in your same predicament, you'll need to learn to get out there in some way, shape or form. Try doing new things that would get you out of the house away from your normal routine, if what your doing isnt working try something new!

I used to be closed up in a shell myself, and i finally just came to the realization the people aren't judging me like i thought. And the people who are dont matter to me anyways, it doesnt just happen though. I started with changing my routine, i just started going for walks, started a new job and met new people and everything changed!

As far as talking and initiating conversation with women, you'll need a boost of confidence. Mostly everyone has a fear of rejection when trying to initiate, its getting past the fear that gets you forward.

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