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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...

< Prev1234567891011Next > [38 pages, 1485 answers]

What does her answer mean?

Q.   I used to hang out with her a lot in high school, but at the time I didn't act on my feelings. Partially because another boy told her how he felt and it didn't go well for him because she was going to leave town for college soon. And partially ...

A.   17 September 2011: "...from what I know about him he doesn't sound like a very good boyfriend." That doesn't mean anything, chicks stay with crappy boyfriends all the time - what a girl considers a good boyfriend is very different from what most guys think of. H... (read in full...)

Girlfriend says she would leave me for famous people in an instant! It hurts!

Q.   I'm 17 and my girlfriend is also 17 She is Christian and waiting until marriage. I am cool with this I am not cool with her telling me how hot other people are and alluding how she would have sex with them and leave me for them in an instant. Gra...

A.   17 September 2011: Chicks do that sometimes. Don't think of it as a bad thing; think of it as a chance to show your resilience in the face of emotional adversity. She says she'd leave you for Hugh Jackman, you chuckle and say, "So, do you think you'd miss me after... (read in full...)

Relationship dynamics: supportive vs. non supportive spouse/partner

Q.   I have observed many couples in my life and I am noticing more and more as I get older that in many relationships, there is an imbalance of how one person treats the other which causes tension, resentment, irritation, and disatisfaction. I'm also ...

A.   17 September 2011: I'm a type B in both cases. I prefer to be the solid rock she can lean on when she needs it rather than going out and crowding her chance to live her own life, and I prefer to be treated the same way. But then, I'm much less long-winded in real ... (read in full...)

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

Q.   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...

A.   17 September 2011: @ chigirl "Therefore I will suggest that what is attractive to a woman is also that a man has dating experience, and has been through a serious relationship before in his life." This is *absolutely* true. From what I've seen, after about age ... (read in full...)

Why is my mom so upset about the way my husband and I treat each other?

Q.   Hello, I am a 31 year old married woman. You have given me great advice in the past. Here is my problem: This is a little long with background. My father and my husband get along great. My dad usually calls him, son, when he talks to him; ...

A.   7 September 2011: Your mom wants you to be happy, but she's conflicted because she thinks there's a certain way for you to be happy, and no other. She will continue to think this despite all evidence to the contrary. Don't let it get you down. Feminists will tel... (read in full...)

He man who says "you deserve better". What does he mean??

Q.   Some of my friends and I are at our wits end when it comes to a certain type of man. We've come across this type of man at least one time each, and none of us are any wiser. It's the man who says "you deserve better than me", and then ends the re...

A.   7 September 2011: It's a way of ending the relationship while saving face - pretty much just a way to avoid having to deal with a fight. Basically, if a man uses this term, he believes you're too high-maintenance or prone to fighting for him to say anything else - ... (read in full...)

Tips on how to ask a girl out!

Q.   Hi everyone, I fancy a girl in my school. We are very good friends and she does know a lot about my past. I am considering to ask her to be my girlfriend. This is not my first time asking a girl out but the last two times failed and I don'...

A.   7 September 2011: It doesn't much matter when or how you do it, so long as you meet the following three elements: 1) Have a plan. Have one day, one backup day, and a plan for something to do. Hint at the plan, but don't reveal everything if you can avoid it. 2... (read in full...)

What Women Want Most From A Guy

Q.   In a continuation to my series of articles on developing "Swagger", I feel it's necessary recap, include, and conclude with these 8 tips. If there's anything additional ladies that you feel is worth mentioning, don't hesitate to add your thoughts in ...

A.   7 September 2011: There's just so much missing from this. All of these points are ones that plenty of romantically unsuccessful guys do all the time, and know they're supposed to do - because they're doing it wrong. The details are too important to leave out ... (read in full...)

Will my strategy to ask her out work?

Q.   She's a good friend, I think we both have feeling for each other, so Im going to make the first move and ask if we could date. Would it be fine (put yourself in her shoes) if I asked her if she had time to quickly meet up during the weekend so t...

A.   2 September 2011: Do not spell anything out explicitly in words. Chicks hate this. Don't tell her you've been thinking about things, or that you really are attracted to her, or that you want her to be your girlfriend. Don't ask for her approval for anything, ... (read in full...)

Dating for Teens

Q.   So here it is. Finally a dating guide for Teens written by a Teen. Dating can seem daunting. I mean first there's the actual asking them out and then there's the actual date. No wonder we're usually so nervous about messing up that we mess up ...

A.   1 September 2011: Just to throw in my two cents... 1) Being friends first is something I would vehemently recommend against. Don't do it. Nine times out of ten, being friends first kills the girl's attraction to the guy, if it was even there to begin with. G... (read in full...)

Will my strategy to ask her out work?

Q.   She's a good friend, I think we both have feeling for each other, so Im going to make the first move and ask if we could date. Would it be fine (put yourself in her shoes) if I asked her if she had time to quickly meet up during the weekend so t...

A.   31 August 2011: It's too formal and high-pressure. Chicks don't like pressure, and they prefer that relationship-related things "just happen," rather than being planned in advance. You're not trying to trick her, you're trying to transition a relationship. ... (read in full...)

Ladies, aged less than 30, would you date a guy even if he isn't ''FUN''?

Q.   Would you consider a relatively young male to be dateable even if he is a 180 degrees from the hard party bad boy persona? I am not saying that I am weak, nor that I can't stick up for myself and who I care about. I simply have no interest in ...

A.   28 August 2011: The fact that you are asking this question implies you've been having a hard time finding girls who will date you with those attributes (if I'm wrong about that, i apologize in advance). This behavior does handicap you in one significant way - it... (read in full...)

If a man hates a woman, why would he want to see her?

Q.   If a man hates a woman and tries to sabotage her and ignores her....? why would he keep trying to see her or either invite her to a party he's having every time before he has to take a long vacation? they have never been in a relationship. they kno...

A.   28 August 2011: Unless there is some pressing social obligation (family, friends, work), either she has attractive friends who he wants to sleep with, or he wants to sleep with her.... (read in full...)

Any advice on how to change myself or come across suitable for kind of man that I need...?

Q.   I am quite an outgoing and sociable girl and I come across as having a strong and perhaps at times a rather domineering personality. This is mainly due to a lack of self esteem and so I over compensate with appearing to be very confident. Howeve...

A.   26 August 2011: Just one thing I'd like to add - the advice to "just be yourself" doesn't really mean anything useful. People have a wonderful capacity to grow, change, and mature with time. Be the best version of yourself. Discard old habits in favor of better ... (read in full...)

My wife says that sex with me grosses her out. Can that change?

Q.   I am 38 and my wife is 41. We do not have sex anymore and have not for at least a decade. She says that sex with me grosses her out. She says that the idea of sex itself does not gross her out, and she fantasizes about sex with other men sometimes, ...

A.   26 August 2011: "It's not so much that she's disgusted by my appearance as it is that the sex act itself is awkward and makes her queasy." That sounds like a lie to me, even in light of her previous abuse. "She says she wants to change, wants to feel sexual a... (read in full...)

He never texts and expects me to chase him!

Q.   im really getting fed up of this guy i know. he knows i like him but i feel like his nurse maid. if he ever has problems im there. if hes ever financially stuck im there yet hes aware i like him but doesnt treat me in a great way. he goes on all ...

A.   26 August 2011: He treats you badly when you're loyal because... when he treats you badly, you stay loyal. You are rewarding his behavior, and thereby enabling it. I'm not certain if you're "officially" dating from the text of the question, but I would suggest ... (read in full...)

Any advice on how to change myself or come across suitable for kind of man that I need...?

Q.   I am quite an outgoing and sociable girl and I come across as having a strong and perhaps at times a rather domineering personality. This is mainly due to a lack of self esteem and so I over compensate with appearing to be very confident. Howeve...

A.   26 August 2011: You're in luck, I've been brainstorming an article on how to be a keeper. After some commentary, I'll give you the paraphrased, rough-draft version. "Although well taught in feminist theory I still believe that it is a man's job to protect ... (read in full...)

Is it possible to have a lasting marriage?

Q.   I read so many questions here about married people who have fallen out of love, married people who cheat, married people who are tempted to cheat, etc. etc. Does marriage even mean anything these days, other than being tied together by law?...

A.   25 August 2011: There is no functional difference between a lasting marriage and a lasting long term relationship. If a marriage functions, it's not because it's a marriage, it's because those two people work well together, and would have done just fine without ... (read in full...)

Roleplaying..my boyfriend wants me to be a hooker and I'm totally stumped on what to do!

Q.   hey guys, just need some help and suggestions. my boyfriend and i have been together for 8 years and are very compatible sexually. recently, we've just started dabbling in a little roleplay and it is amazing. i usually pick up roles well, bu...

A.   25 August 2011: The outfit's easy enough, just get the sluttiest things you own and put them together regardless of whether they match. For the attitude, start off all business, as if this is literally no big thing to you, you're just in it to get paid quick. ... (read in full...)

Taking it slow... from a guys point of view please!

Q.   I'm in my mid 40s and I met an amazing man of the same age. We actually went to public school together but recently connected through facebook. We've had three fantastic dates over a period of 2 months and are clearly attracted to one another. We've ...

A.   24 August 2011: Go ahead and contact him whenever you feel like it. Keep it to the point - call to set up a date, or a time to meet him, or else just send a text to let him know he's on your mind. Guys don't tend to be as enthusiastic about just talking on the ... (read in full...)

Wife doesn't want to leave me, but isn't 'in love' anymore. She's happier with her FWB.

Q.   I'm a married man, and my wife has just said that she still loves me but is not in love with me. She says I'm a great father and husband and she doesn't want to hurt me. Then, she explained, she has a friend which has gotten into the "with benefi...

A.   24 August 2011: So... she's saying that you get to keep doing all the nice, husbandly things like providing for her, caring for and protecting the kids, and being faithful to her... but she gets to go out and flout your marriage vows? "...not knowing if she's ju... (read in full...)

Taking it slow... from a guys point of view please!

Q.   I'm in my mid 40s and I met an amazing man of the same age. We actually went to public school together but recently connected through facebook. We've had three fantastic dates over a period of 2 months and are clearly attracted to one another. We've ...

A.   23 August 2011: When a guy says you can date other men, it's a sign that he is deeply hurt by his last experience with a woman. He either assumes you'll already be seeing other guys anyway, or he feels like you'll leave if he tries to put any pressure on you at ... (read in full...)

A question for the guys! How important is it to last in bed?

Q.   This is a question for the guys! Ok, how important is it for guys to last during sex? I ask because my new boyfriend only lasts about 2 minutes before he comes and now hes shying away from sex. To me its not a big deal, because although it woul...

A.   21 August 2011: "To me its not a big deal, because although it would be nice to have an orgasm myself, I enjoy sex for the closeness and intimacy rather than orgasm." In his mind, when you say this, he thinks, "Yeah, she says that now; in a month, she'll be telli... (read in full...)

14 year old student hitting on me. How do I solve this?

Q.   This 14 year old girl has a obsessive crush on me. It all started when I was looking for a part time job. I’m a college student and I’m living in an apartment with my roommates. As I was good in maths I decided to teach maths at high school to t...

A.   21 August 2011: Do as Abella says, this girl represents a serious danger to you. People are crazy, and will take even the slightest hint of impropriety between the two of you far more seriously than is warranted. You need to get as much documentation set up a... (read in full...)

Why don't girls look at me?

Q.   I have a question, mainly for girls. Why don't girls look at me? If I'm with someone, likely they will look at the other person more than me. For example, today I was sitting at a table opposite a friend at work. This girl who I vaguely knew s...

A.   21 August 2011: She's paying attention to whoever she finds the most attractive. This does not mean she has a crush, that that she's attracted - there's a difference. It also does not mean you have no shot. One of the downsides of being a guy is you're going to ... (read in full...)

A woman with a high status position,is it a turn off for blokes?

Q.   because I run my own business i cannot seem to find a man that wants me,or is it because i have a child?...

A.   21 August 2011: Owning your own business won't scare away a guy by itself, but it does put the guy on high alert for ball-busting attitude. The belief is that women are simply not attracted to men who earn less than they do (I think this belief is largely ... (read in full...)

Porn: sometimes it's helpful

Q.   I’ve read countless posts about porn. Women saying porn is killing their self-image, ruining their relationships. Men replying that it just goes with the territory, get over it. By and large the women having a problem with porn are young (18-25)....

A.   18 August 2011: Normally I'm pretty pro-porn, but I'm going to leave that point untouched for now just to address another one. "As the kids got older, well, you wouldn’t want them to hear anything." This sounds like part of the problem with your wife. Sex ... (read in full...)

I feel so ugly and gross! My only boyfriend just broke up with me...

Q.   I feel so ugly and gross... I recently broke up with my only boyfriend. Granted, I'm only 22 and I met him when I was 17. It was a long, serious and intense relationship. We had a lot of issues but we always thought love could help us make it. ...

A.   16 August 2011: Ouch. You're going through a rough spot. Ending a five-year relationship is going to suck for a few months, there's no way around that. Just remind yourself now and then not to take the things you say about yourself in grief seriously. I'd say ... (read in full...)

How many of the men actually enjoy going down on a woman?

Q.   Why is it that some men prefer not to go down on a woman? Should I interpret this as a sign he doesn't love me or just let it go and enjoy the rest of the "act"? And the other way around: how many of the men actually expect having oral sex performe...

A.   16 August 2011: I don't enjoy it for the act itself, but I enjoy seeing her happy, and I consider it fair play - so I go into it with enthusiasm. If your man doesn't enjoy it, it does not mean he doesn't love you, it just means he doesn't like going down on you. ... (read in full...)

Do men mind a woman who has asymetrical breasts?

Q.   Can I have help from just guys please? I have breasts that are slightly asymetrical not by much like a cup size. They are both pert and the rest of my body is toned and in proportion. I just want to know if guys really mind if my boobs arent th...

A.   16 August 2011: Boobs are always slightly different - and yes, men notice. As long as they aren't wildly different, we won't care. Even if they are (I'm not sure if you mean a full cup size, or less than one), I could easily see a guy getting to like them ... (read in full...)

What do guys feel during sex? Is it more emotional or more physical or both...?

Q.   I have been asking my boyfriend what sex feels like for him and he can't even put it into words because he said it feels so good. I get more of an emotional feeling from it than physical. For the guys , could you tell me what he's feeling? I'm just ...

A.   16 August 2011: Changes from time to time. There's long, slow lovemaking, which is a profoundly emotional experience, and then there's quickies in the laundry room, which are a purely physical one. Most sex falls somewhere in the middle. What does stand ou... (read in full...)

What kind of immature cop-out is the "the chase"?

Q.   Why can't guys have honest, loving relationships? Are they not man enough to have them? If I care for a guy, why do I have to play coy and hard to get for his attention? Mind-games are disrespectful and hurtful. If he doesn't want the comfort, ...

A.   16 August 2011: "Mind-games are disrespectful and hurtful." True, but they are also effective. I avoid them because I'm a romantic at heart, but it would be foolish to deny that they work. The better a guy is at these games, the easier he finds it to get laid... (read in full...)

How can I fit in ? will things be different this time ? Am I going to be able to catch up

Q.   Hey. Well basically I'll try and keep this short, after the summer holidays it has been decided that i am now going to go to a new high school. I've missed about 6 months of my education and am extremely behind and I've been being home tutored ...

A.   15 August 2011: You sound like me at your age. Got a few things for you to keep in mind. First, the worst thing about depression is that ordinary, common "bad-day" stuff feels like the end of the world. Depression magnifies mild consternation into serious ... (read in full...)

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

Q.   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...

A.   15 August 2011: Thanks for the feedback, Mishmash. While I agree that these are generally useful traits, I don't think these are the ones that women should focus on most. I considered writing a similar list for women, but gave up because as a straight man, I h... (read in full...)

Is high status a turn on for women?

Q.   For those women who care what others think of their BFs, is high status itself (not his confidence) a sexual turn on like boobs are for men? Eg. a TV presenter, CEO, famous musician, etc....

A.   15 August 2011: I recall reading a study that women have more orgasms with rich and high-status men than with low-status men; I'll have to see if I can dig that up later. More importantly, a woman's ability to orgasm is not as "mechanical" as it is with a guy. ... (read in full...)

Is it normal for guys to tell white lies?

Q.   Hi! Any help would be greatly appreciated! Is it normal for guys to tell white lies? I keep catching my bf telling me little white lies. It actually bothers me, but I can learn to accept it if all/most guys tend to be like this. Examp...

A.   15 August 2011: Stories get a little better every time you tell them, and recall isn't perfect. If he stands to gain something (besides a more interesting story) from a white lie, you might consider if there's something up. If he doesn't gain anything meaningf... (read in full...)

Why do creeps ask girls if they are virgins?

Q.   Why do creepy guys and perverts ask teenage girls "Are you a virgin"?...

A.   15 August 2011: Some guys like the idea of claiming a virgin; others don't want that responsibility (or the clinging associated with it), and avoid it. Non-creepy guys ask it too (to girls close to their own age); if they don't ask older women, it's because they ... (read in full...)

Leave a condom inside?

Q.   Why would a guy leave the condom he used inside the girl?...

A.   15 August 2011: ... I can't imagine someone being this crude. Please tell me it's a hypothetical question; barring that, can you give a more specific description of the circumstances, in the hopes of shedding more light on it?... (read in full...)

Wife says the root of our arguing is that she does not trust me--even tho I have never lied or cheated!!

Q.   Hello all. I recently asked for advice about how to renew the spark in a very argumentative marriage. I recently found out some news that explains a lot about the arguing. My wife told me last night that she doesn't trust me. She said she jus...

A.   14 August 2011: From what you say, you're doing fine as a husband - getting married at all was probably not the wisest move, but you're doing it right. I'd say it's about a 2/3 chance that she's just chronically neurotic, and there is absolutely nothing you can ... (read in full...)

Guy I like asked me to stop texting him and that he would hang out when is life is more together. What does this mean?

Q.   Hi ive been talking to a guy. We lost contact from high school,but started talking again when we found each other on facebook. we have even hung out a few times. although a few times we did plan but never happened because he was working late. ...

A.   14 August 2011: There's no hidden meaning, he's busy, cash-strapped, and stressed out. Some people deal with stress better by withdrawing from others than by reaching out to others; maintaining a social life beyond the bare minimum is probably only adding to his ... (read in full...)

Should I study film in college, which is my passion, or get another degree as a fallback?

Q.   I know this is relationships but i really could use some third party advice! I'm going to university and want to know whether i should study the what i hope to pursue a career in, or whether i should study something else?? Basically, i w...

A.   14 August 2011: Get a more useful degree, something applicable (Anything outside of liberal arts - try math, science, engineering, agriculture, even business). If filmmaking is your passion, make and edit films in your spare time with friends. The film industry... (read in full...)

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