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“Because awkwardness, at its core, is all about believing that everyone else knows exactly how to navigate a social situation, and you're the only one who hasn't figured it out yet.” – Daniel O’Brien

If you wish to PM me, and are referencing a particular question, please link to that question (just copying the url is enough).

Latest articles:

"Be Yourself" is Pointless Advice

This question has 2 answers by readers of DearCupid.ORG.
Newest answer was posted

27 August 2011: Let's leave aside for now the fact that philosophers have pondered for millennia what the "self" actually is. Not going to get into that, most of those men were a lot brighter than I am (okay, all of them were, but that's not the point). Inst...

How to be Attractive, a Beginner's Guide for Men

This question has 5 answers by readers of DearCupid.ORG.
Newest answer was posted

2 August 2011: This is mostly a repost of some advice I posted a while back; Cerberus seemed to like it, and Tisha suggested posting it as an article. Things have been expanded on or reworded a bit. Note that the title is not "How to get a girl," or "How t...

Marriage - why should any man bother?

This question has 29 answers by readers of DearCupid.ORG.
Newest answer was posted

23 July 2010: Women… why should any guy propose marriage? Full disclosure: I have never been married, but several family members and friends have been hurt by divorce, and I know of only a handful of happy marriages over one year old. My feelings for the...

My friend is the odd one out?

Q.   Ok so i live in a small town where I grew up with all these girls. Iv'e known them since we were babies. We are all 17 theres about 14 of us all together. But one of my friends Naomi havent changed at all. she's still young in the mind. She doesnt ...

A.   8 July 2010: Also, playstation and DS are fun. Why shouldn't adults play them? It is quite likely your friend has become more catty and judgemental because you have pushed her for so long to do things she does not want to. You get what you give.... (read in full...)

Is it worth trying and holding on to her?

Q.   I'm 20 and i'v been out of school for about a year and 1/2 and i dont really feel like going back yet, but i have a girlfriend that i really care for that is going to collage soon and i dont see her much as is but once she starts school im afrade ...

A.   5 July 2010: Long-distance relationships have, according to the American Psychology Association, about a 5-8% chance of working out. People know that they don't work, and that knowledge alone can hurt a relationship about to go into long-distance. Being... (read in full...)

I think I'm stuck in the friend zone now, but how do I get out?

Q.   i recently ask a girl out who i have really like for at least 2 years now, and she said no because 'she loves me as a friend'. however, i don't want to give up on her, because to me she is far too special to let slip. is there any way i can get past ...

A.   5 July 2010: You have control over your own actions, and to some extent over your own feelings, but not over those of others. You can, however, try to understand what she is feeling. Being a friend to a girl who you are romantically interested in, then fai... (read in full...)

My neediness and insecurity is costing me my relationships!

Q.   My name is, James. I am 35 years old and really need help. I have been single for a long time. I recently became involved with a woman and through my neediness and insecurity have already lost her. I have always been this way and I am not sure how ...

A.   5 July 2010: Have your friends set you up with dates to get past the fear of rejection. And consider: rejection is just someone who does not know you saying "No," so it is not an informed judgement of your character. You lose nothing by being rejected. ... (read in full...)

I really don't know if I want the truth because then our relationship has been built on decite and lies.

Q.   I have been married for a long time and I believe we love each other. My wife claims she only had one sexual relationship before me but it was multiple times. I had to learn this from friends before I confronted her and she admitted it to be true. I ...

A.   5 July 2010: This is called retroactive jealousy. It is completely normal. Your brain, evolved from that of cavemen, is trying to protect you from the possibility of getting cuckolded. This instinct is extremely powerful; men have and still do kill over it. ... (read in full...)

Someone please help me with my husband!

Q.   [Mod note: Combined two questions as they are both about the same marriage.] i am a 22 year old mother of two i have been married to my husband for over a year now we have dated since high school for the past eight years.in 2007 he gotten inca...

A.   5 July 2010: Your husband will never change. He is bad for you and for your children. I really hate to say this to someone who is obviously in such distress, but having his children and marrying him were both mistakes. Get away from him, file for divorce,... (read in full...)

How do I change our sex life so that it's amazing every time?

Q.   Just yesterday my boyfriend and I were really aggravated at each other. So, as we were laying down I asked him why he was mad at me. He began to explain why, and on top of the first reason there were a few others. When we were done talking, ...

A.   5 July 2010: You have to "man up" and tell him what you like in bed. He's mad because A) he wants to please you, and B) because he believes that if he does not please you, you will leave him. There's nothing to be embarassed about. Once a guy's been inside ... (read in full...)

How can I get over my paranoia or convince her to try the pill?

Q.   Hello, me and my girlfriend have been together for about 6 month now and everything is going good. we see each other about 5 days a week and have a lot of fun together. im 19 and she is 16 by the way. the thing is, we have yet to have sex, which is ...

A.   5 July 2010: A) This is not paranoia, this is an entirely healthy concern. A child would screw up both your lives right now, and you should *not* have sex without some form of birth control. Notably, condoms are effective against STD's but are onyl slightly ... (read in full...)

I never seem to make it past the dating part of the relationship!

Q.   Dear aunties, I never seem to make it past the dating part of the relationship, it never seems to become official. I know I'm not clingy, I show interest appropriately and I'm just picky enough to where I'm not settling. I recently went on a...

A.   5 July 2010: It sounds like you are not putting out on the first date. That's a good thing, so you're halfway there already. Giving it up on the first date is a guaranteed way of not getting a second one. Also, the good-nigth kiss means nothing; just because ... (read in full...)

He copies moves and words from porn movies! It's not romantic and it's not helping my insecurities!

Q.   hey there, i know you probably read these questins all the time but here we go. im 17 and my boyfriend of 21 have been together for a year, and recently i have become very insecure in my relationship. every day i dont think i am good enough or ...

A.   5 July 2010: Two hours a day at 21 is... well, a bit much. Where does he find all that time? Does he have classes, a job, or friends? As for acting it out on you, to a certain extent, it's healthy and fun. This sounds like it's beyond that point. Ask for ... (read in full...)

I'm lying to my parents to see my boyfriend

Q.   I love my boyfriend so much but it means lying to my parents i hate lying to them. if they find out i will not be allowed to see him. At 14 they dont approve and see me as a child still. i want to see him still, but i want the respect of my loving ...

A.   5 July 2010: I'll assume he's your age for this post. If he's older (17+), then your parents are right and you should not be with him. If he's your age, your parents concern is that you will fool around and get pregnant. What evidence do they have that you... (read in full...)

I miss my boyfriend and want help

Q.   i have been with my boyfriend for nearly 3 years we were sooo good until i stupidly ended it just before Christmas, we got back together in feb but found it hard as i struggled with trust, he finished me then because i was always on at him he has ...

A.   5 July 2010: You've done some pretty serious damage to his trust. Getting back together works sometimes, but not the majority of the time, and he knows it. How can you guarantee that if he gets back with you, you won't just dump him again? Your word will not... (read in full...)

Interested? Or just sex?

Q.   Ok how can i tell that a guy is really intersted in me or just want to have sex?...

A.   5 July 2010: The answer is different, depending on whether or not you've already had sex. If so, cutting him off from sex will make him think *you* have lost interest. Even if he is interested, this will be a strong incentive for him to leave you. Your bes... (read in full...)

Could I be a couple months pregnant and not know it?

Q.   my boyfriend and i have been together for about 7 months now, and have been sexually active. this is my first month off the pill after being on it for 3 months, and since i went on the pill, we have not been using protection. i have been really ...

A.   5 July 2010: Going on and off the pill screws up your hormones awfully. If you've been having them, you're not preggers. Your period tomorrow may be a day or two late even if you're not pregnant. The pill works by using synthetic hormones to actually... (read in full...)

My mom and my brother don't approve of the guy I want to date, what should I do?

Q.   Sorry for how long it is. Skip to the bottom for the abridged version, or read the whole thing so you know exactly what's going on. To help better understand my problem, I'll explain my relationship with my younger brother. I'm 17 and he's a year ...

A.   5 July 2010: First thing that comes to mind: Guys will *never* be content just to be friends with girls they like. He *will* make a move someday, and lust after you until then. It will be torture for him, and awkward for you. Your mom and brother want wha... (read in full...)

So wrong, but could he be Mr. right?

Q.   I recently broke up my boyfriend, because he never touched me, he never initiated coversation with me, and he would always be touching my best friends. I couldn't take it, so I broke up with. I went out with him for about four months, but sometime ...

A.   5 July 2010: It's not wrong, but if you pursue it, there will be drama. The best friend may even choose to abide by "Bros before hoes" and leave you rather than face the drama. If that risk and is worth it to you, go for it, and be ready to accept the outc... (read in full...)

How can I make my girlfriend forget this other guy and come back to me?

Q.   hi i thank you before answering my question...so i have a girlfriend and we have child and when she was pregnant i passed from a very diffcult time and i wasnt that helpful,apart from that she always liked this guy and now she's liking even ...

A.   5 July 2010: Your question has so little context, it is basically impossible to give a good answer. The grammar doesn't help either. To give some general advice... Make it clear that you are the father of her child, that your first priority is the kid, and... (read in full...)

Is it normal that I like him? Or is it wrong?

Q.   Okay, this is the story. My best friends neighbor is geting really close to us. He is so nice and extremly hot. Lately, we've been hitting on each other, and kissed a little. I was pure presured by my friend to do it though! I'm starting to like ...

A.   5 July 2010: Sounds fine and normal to me. Just be sure to look up and abide by the age of consent laws in your state/province. ... (read in full...)

Heavily pregnant with a boyfriend who is unsupportive!

Q.   Hi all. im 8 months pregnant and my bf is unemployed at the moment and so stressd out and he never calls me nor text me. weve been together for atleast 10 months now. he was madly in love with me but now he is distant. i feel like dumping him n ...

A.   5 July 2010: You let a guy impregnate you after knowing him for two months... yeah, if he's being "distant" but is still with you, you've gotten incredibly lucky. Most guys would have run the hell away. I doubt he will make a good father, husband, or boyf... (read in full...)

Ex-girlfriend has moved on, though I just can't, for some reason....

Q.   So here it is...yet another guy who for some reason cannot get over what happened with his ex-girlfriend... I stress that it's not that I can't get over her, or even that I want her back just that I cannot get over what she did...it makes n...

A.   5 July 2010: No one owes anyone "closure". When the relationship ended, both of your obligations to the other ceased to exist. You were hurt, and she appears to have gotten away unpunished. That hurts your sense of justice, but it's just the way life works o... (read in full...)

What is a multiple orgasm, what is an orgasm, and do guys have them?

Q.   hi frns,, i want to know about multiple orgasms,, well i don't even know what is an orgasm and do guys also experiance orgasm,, waiting...

A.   5 July 2010: Orgasm is, medically, speaking, the contraction of the PC muscle at the base of the pelvis during intercourse or masturbation. In most people, this is an extremely pleasurable sensation. In males, the orgasm is most often accompanied by e... (read in full...)

Why is he ignoring me for so long?

Q.   I am in a ldr(long distance relation)for about 5 years. My bf is angry with me for getting him in trouble at work by being I admit annoying and over texting him. I realize I was annoying, and didn't consider his job but I believe I just miss him and ...

A.   5 July 2010: Stop texting, for one thing. Call him at night and talk then. You can figure out what he actually means much better if you can hear his voice, and if he is not trying to text really fast while his boss is not looking.... (read in full...)

Thinking of ending my marriage for someone else.

Q.   Dear cupid, I met my ex boyfriend when I was just 16. He was 34! I lied to him about my age and he broke it off with me because of my age. He told me to call him whn I turned 18. There was a definite spark between us and a feeling I have neer felt...

A.   5 July 2010: If you think God wants you to leave your husband for this new guy, you really ought to start going to church again. Your body built a strong pair-bond with this first man when you were with him. You were young and susceptible to it. Your brain ... (read in full...)

Should I change my decision?

Q.   Well..typical I like two guys problem =[ This is just so hard man, and there's like no one to talk to because everyone says I should just forget about the other guy because I have a boyfriend.. WHOLE STORY: Boyfriend(let's call him Joe,w...

A.   5 July 2010: Bob has to accept that some relationships don't work out. You didn't know he would get so infatuated when you used him, so you are only partly to blame. In fact, leaving a guy with those sorts of issues is a *good decision*. That relationship ... (read in full...)

My friend is the odd one out?

Q.   Ok so i live in a small town where I grew up with all these girls. Iv'e known them since we were babies. We are all 17 theres about 14 of us all together. But one of my friends Naomi havent changed at all. she's still young in the mind. She doesnt ...

A.   5 July 2010: She's fine. You're trying to be a good friend by helping her fit in, but if she's not comfortable drinking, don't make her feel left out for her decision. I don't know if it's the same for girls, but one of my best drinking buddies actually never ... (read in full...)

Is it normal for males to like this stimulation?

Q.   Hi! :) .. I have a really very strange question to ask.. Yesterday morning my bf and I were having sex, the first time in 2 weeks that we have had proper intercourse. Although the strangest thing happened about a year ago he bought me a vibrator, ...

A.   5 July 2010: It feels good on all guys, physically speaking; the anus leads to the prostate, which is basically the male G-spot. The reason it's uncommon is because most straight males (and some gay ones, for that matter) are not mentally comfortable with it. ... (read in full...)

He proposed over two years ago, but we are no closer to being married!

Q.   My fiance and I have been together and lived together for 8.5 years now. He proposed 2.5 years ago. We bought a house together this year. Whenever I bring up getting married he becomes upset and last week he told me he "isn't ready". I am in my ...

A.   5 July 2010: After eight years with a guy, and being in your mid-thirties, you'll have to accept that the dating scene is going to be *brutal*. You will have to settle for a guy you probably will not like as much as the current man. But if children are ... (read in full...)

Is it right for a boyfriend to say that he should always be your top priority?

Q.   I'd like your opinions about this. Is it right for a boyfriend to say that he should always be your top priority, meaning even more important than your friends and family, e.t.c ?. Personally, i think everyone should be treated equally. i dont think ...

A.   5 July 2010: Well, not *everyone* in your life should be treated equally. Family always comes first, long-term friends before new ones, and so on. It sounds as though he is reacting to being put off for dates. Did you cancel a date for a girls' night out... (read in full...)

After we had an affair he's having commitment problems.

Q.   I met someone at work 12 years ago. He was co habiting and had children but was not married or in love with the mother anymore (he said), but would not leave out of love/duty etc. for/to the children (does this really happen?). He pursued me ...

A.   5 July 2010: "Does this really happen?" Yes. Some people actually put their children before themselves. They still have needs, though, and if he saw a way to meet his needs without abandoning his kids, I'm not surprised he took it. "Inevitable affair."... (read in full...)

What is the best way to prolong sex?

Q.   [OP original title] What is the best way to prolong sex?...

A.   5 July 2010: Prolong masturbation. From now on, whenever you masturbate, try to make it last at least ten or fifteen minutes. This will get your body used to the longer sex sessions. Additionally, after you get off the first time, continue to hug, hold, an... (read in full...)

Am I really in love?

Q.   Right, im 13 and im with my girlfriend, ive been with her for going on 4 months. We've done loads together and I never stop thinking about her, im thinking of her now as i write :'), but we really love each other and she means the entire world tp ...

A.   5 July 2010: You're infatuated, not in love. At your age, your body is naturally emitting hormones - mostly dopamine - that will literally addict you to her presence. This "high" can last anywhere from a few weeks to a few months, depending on your level of ... (read in full...)

Bumped into my ex and he said he'd wished we didn't split up... oh noooooooo why did he say that???

Q.   I'm 26 years old and I have a 2 month old baby with someone I no longer have feelings for. We are both there for our baby but our relationship has become so bad that I cant talk to him without feeling angry or frustrated. Basically, alot happened ...

A.   2 June 2010: Your ex does not care about you. He said he did, either because he has not been laid in a while, or because he wanted to mess with your head. Get back with him, and you will get burned again... only after this time, you probably will have sca... (read in full...)

Girlfriend of 4 years left for ex of 4 months. PLEASE HELP

Q.   I'm in a tricky situation here and need all the help I can get. I had been going out with this girl for more than 3 years. If you add the courtship period, it should be somewhere around 4 years. Last month, all of a sudden, she stops talking to...

A.   2 June 2010: Don't take her back, obviously. You got that one figured out on your own, which puts you two steps ahead of most people in your situation. Her feelings are *not* based on any rational assessment of your worth as a man. You are *not* any worse of... (read in full...)

Does a relationship really happen because of butterflies?

Q.   My ex girlfriend told me that she wants to be single and we should just be friends. I can honestly say we have love for eachother but she doesn't think our relationship will go anywhere. She met a guy a couple days ago and she told me that he gives ...

A.   2 June 2010: You sound like a decent guy, and this sounds like your first time getting dumped. This is a life experience we all have to go through before we learn that there are plenty of fish in the sea. Chicks are ruled by their emotions. Butterfl... (read in full...)

Why does the man you love need to be so controlling?

Q.   My question is why does the man you love need to be so controlling? I was married to him for 29 years. He left me for a younger woman then she died and he came back into my life. I am in her house with him but he wont let me bring my home things ...

A.   1 June 2010: Women like to be with strong, confident men. Some women exaggerate this desire and seek out domineering, controlling men. Even enough to get back with him after being dumped for another woman. You are at least in your fifties, correct? 29 yea... (read in full...)

She says she's not bothered whether or not she has an orgasm!

Q.   hi there im going out with this girl and we have had sex. she has never had an orgasm ever and i really want to giver her one. i know i can but she says she doenst really care whether she orgasms or not. i respect that but im still going to try. but ...

A.   1 June 2010: She probably *thinks* she's telling the truth. It's your job to show her she's wrong. Google should show you everything you need to know.... (read in full...)

My husband isn't always turned on by me when we have sex and so sometimes he will fantasize about other women to get excited.

Q.   My husband isn't always turned on by me when we have sex and so sometimes he will fantasize about other women to get excited. This hurts my feelings and I feel insecure because of it. Is this something that normally takes place when a man has been ...

A.   1 June 2010: Your age bracket says 36-40. The problem is simply a fact of biology; you are almost certainly less attractive now than you were five years ago. Leaving him to find another man will be difficult, and the man you find will almost certinaly be less ... (read in full...)

How can I open up to him more when he talks about sexy stuff?

Q.   im 19 and in my first ever relationship. my boyfriend always says sexy stuff to me and i never know what to say back. i look like an idiot and he gets a bit annoyed that he's the one that always does the talking in terms of sex. when he asks what i ...

A.   1 June 2010: Are you sleeping with him? If so, follow the next two lines of advice: Practice this line in front of the mirror: "I don't know... but I can learn." [sexy smile] Play up the innocent routine. End these conversations early and get a practical ... (read in full...)

Totally confused about everything in my life...

Q.   So I'm a guy and I'm 15. I live a very boring life, in fact i have no life at all and no TRUE friends. It sucks. It's pretty lonely and sad. And lately I've been getting a real desire to find someone to call my own. To be in love, to fall in love, ...

A.   1 June 2010: Life doesn't start until your mid-20's for most guys. Be patient, study hard, get a good job, and save up some money. Learn to love yourself and others, not because it will make them love you, but because it feels good to do so. Love and good... (read in full...)

Do I deserve this treatment? Am I the bad guy?

Q.   Do I deserve this treatment? Am I the bad guy? (be prepared to read)? First off let me give you a jest of what him and I We’ve been together for a year and a half, we’ve known each other for about 4 years or so, we lived together for 4 months at ...

A.   1 June 2010: His brother is in jail, he swears at you, he needs money for haircuts, and locks you out of the house. You pretend to be asleep so you won't have to spend time with him, describe half of what he does as mean, and wonder if you're the bad guy. ... (read in full...)

What's the best way to test if a guy is interested in me?

Q.   What's the best way to test if a guy is interested in me? in a subtle manner! so that if he isn't, i can walk away without a dented ego!?...

A.   1 June 2010: Interested? Easy. Go talk to him. Does he stare openly at your tits? He onyl wants sex. Does he not stare at your tits? He's not interested. Does he glance at your tits every now and then, especially when you're not looking? He's inter... (read in full...)

Please put my mind at rest!

Q.   Okay, so my girlfriend and i were messing around. we don't believe in having sex, however the other day she gave me a handjob... and i got some on my fingers... about ten minutes later i touched her vagina.. Am i safe? Is she pregnant?...

A.   1 June 2010: Your odds are pretty good that she's not preggers. Still might want to take a morning-after pill, though. Be warned that the pill is going to screw with her hormones, so expect crankiness and odd behavior. Let that be a lesson to be more car... (read in full...)

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