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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...

< Prev2223242526272829303132Next > [38 pages, 1485 answers]

I need my willpower back so I don't reply to him online

Q.   Hi, recently i've finally come to the conclusion that having a certain person in my life is not a good idea anymore. I wish i could change that, believe me but i know i just have accept that it's not going to work. A little info: this guy i...

A.   30 October 2010: Don't let him tempt you. Politely inform him that you are done with him, and delete all his contact info. AIM name, phone number, everything. If he tries to contact you, ignore it and delete the callback number or text. Taking half-mea... (read in full...)

How do I stop these thoughts of other men?

Q.   My boyfriend and I have been together for over a year. Before I met him, I was promiscuous for a few reasons. I really do enjoy it though. I've been called a nympho before. The point is, I have a past and my boyfriend knows about it. When some...

A.   30 October 2010: You're ont he right track. Think very carefully before you do anything to lose this guy, though. Guys who can get past a girl's promiscuous past are few and far between - and rightly so; it's very difficult to identify that small portion of ... (read in full...)

What do I do if I think I can't kiss?

Q.   What do I do if I think icant kiss like will a boy even care if I can or not if they like me to much ?...

A.   30 October 2010: Guys your age won't know the difference. There's not much to learn for basic proficiency, anyway; a little practice will make you acceptable to anyone, if not exceptional.... (read in full...)

Fingering and cherry popping?

Q.   is it possible for a guy to 'pop your cherry' by fingering?...

A.   30 October 2010: Physically, yes, they can break the hymen that way. However, most guys don't consider a broken hymen sufficient to count as lost virginity. Many girls break it doing gymnastics or soccer long before they have sex. Basically, fingering doesn't ... (read in full...)

We're twins but the guys think my shorter sister is more attractive

Q.   I am 5'8" and my twin sister is two inches shorter than I am. It seems like all the guys think that she is more attractive. Is it because she is shorter than me?...

A.   30 October 2010: While some guys really like short girls (I'm one of them), for most guys height alone is not enough to make the difference. It may be that she looks noticably different then you, or that she carries herself differently. Maybe she is more outgoing ... (read in full...)

Do I lose my virginity having anal sex?

Q.   My boyfriend and i want to try anal. Is there anything i should be worried about? Well it hurt me? Will i lose my virginity??...

A.   30 October 2010: Technically, int he most literal sense, no, you haven't lost your virginity. However, most guys would consider this sex, and if you did not count it, they would feel like you lied to them. If it matters to you what guys say in the future, then ... (read in full...)

I think I'm ugly

Q.   Well,I think Im ugly,,,,,,I have a flat but,bushy eyebrows but that all wrong.But guys where I live hate flat butts.:( Then the girls I hang with are all really pretty,and have all been in a relationship,had a kiss or whatever,but me?Nope.The guy I ...

A.   30 October 2010: Well, what you lack in look you'll have to make up for in personality and intitiative. I know women really prefer to be chased, but if the choce is between being single and stepping out of your comfort zone, I know which I'd pick. So, make a m... (read in full...)

In the heat of the argument I told him he has a tiny penis! I know I have screwed up, so how do I fix this?

Q.   Ok so ive been seeing this guy for a while now almost a year. He told me before that he always thought he had a small penis (he had been drinking, in fact i dont know if he remembers telling me that) but hes not small hes like 6.5 in. Ive been told ...

A.   30 October 2010: The other posters have done a thorough job of tellign you the magnitude of your error, and you sound as though you've taken the lesson to heart. There's an unadressed point at work here. Besides the hurt directly related to his penis, there is... (read in full...)

I lost weight and now my husband thinks I'm cheating?

Q.   I been with my husband for almost nine years we have 2 wonderful sons. A couple of months ago i got hurt at work so i was at home doing nothing which i started gaining weight. My husband never told me oh ur fat. Evevery thing was going fine. Well i ...

A.   30 October 2010: Good on you for losing the weight. Far too many married folks fail in that. To be fair to your husband, he's probably heard quite a few horror stories about wives losing weight only once they cheat. The reason he did not initially complain... (read in full...)

Airports new "feel you up" measure is crossing the lines!

Q.   ok. who was watching cnn this morning? airports are bringing in some new security measures and its getting personal. i watched (on cnn) an employee run her hand between and right under a female passengers breasts. they touch your butt and quickly ...

A.   29 October 2010: Not exactly a dating question, but interesting anyway. Besides the feeling up, there's also the full-body scanners that give a wonderfully detailed 3d map of your naked body to a security guard. Supposedly the electronic copy is erased afterwar... (read in full...)

Should I let it go, even though I need closure?

Q.   when i was on a school trip i completely and utterly fell for a boy. Halfway through the week we got together and we moved fast (boys and girls weren't allowed in the same room for a reason - we didn't have sx but a few more days and we would have ...

A.   29 October 2010: No one is entitled to closure. It's a nice thing to do, but once you break up unilaterally, the whole thing is over. You'll be happier if you don't worry about closure, and just move on. Don't give some guy who dumped you any more power over you... (read in full...)

Why won't he perform oral on me?

Q.   My boyfriend simply won't go down on me. We have been sexually active for over 3 months and I've received it maybe 6 times. I give him head all the time, hoping to get some in return, but he claims he just has to be in the mood for it. I can't stand ...

A.   29 October 2010: Why he's not doing it: some guys just really don't like it. Either it's the taste (no matter how clean you are), or they aren't getting any stimulation out of it, or it's psychological. A friend of mine stopped doing it for his girlfriend, and ... (read in full...)

How does one deal with a commitment-phobe?

Q.   How does one deal with a commitmentphobe? I know that he more than likes me. He has proven it on many occasions over the past year. He just freaked when I mentioned the word relationship. He is still around writing, calling, caring. He took abuse ...

A.   29 October 2010: Confusing, yeah. That's almost the opposite of what you wrote the first time. If it was just that you wrote too quickly, I understand. If he's been trying to get inot your pants for a full year, he probably really does like you, and is just afr... (read in full...)

Why do men think of women as slaves?

Q.   why do men think of women as slaves?...

A.   29 October 2010: I know this is troll bait, or else someone posting at random in a bad mood, but I'm gonna be a sucker this once. If it's housework you're worried about... Men have labored, fought, and died since the beginning of civilization for the women an... (read in full...)

I didn't tell my online guy that I had a daughter till after we met, now he won't talk to me!

Q.   I met a guy online he was in iraq at the time.I never belived in dating sites before,it was my first time chatting with someone oline we start chatting and he was so sweet the more we chat the more I liked him,on one of our chats he asked me if I ...

A.   29 October 2010: I hate to say this, because you sound truly penitent, but I don't think he's going to get over it. I don't think I would, in his position. Let's go back to your original post: "I have very strong reason not tell him the truth and I did't feel... (read in full...)

I can't stop masturbating over my co-worker!

Q.   i need help i work with a polish women shes 23 small blonde hair big boobs face and smile like you wouldnt beleave she just looks awesome, shes so friendly get on well every time i speak to her or even look at her i get an massive erection neve...

A.   28 October 2010: Doing it at home is fine, but if you're doing it at work, you need to seriously calm down and focus on regaining self control. I do agree that eastern European women are awesome, but there's a time and a place. Keep some ice water at your des... (read in full...)

29 year old virgin and waiting for the right one. Will I find her?

Q.   hi am 29 many say am a good looking guy, thing is i have allways bin shy around women god knows why some girls ask how come u havnt got a gf ya such a lovely guy thing is am still a virgin i wanted to save myself for the right person am not re...

A.   28 October 2010: I'll try to break this down for you. "some girls ask how come u havnt got a gf ya such a lovely guy" Women always say that. It's intended to make you feel better, but that's all. Never listen unless the person saying it is actually trying ... (read in full...)

The only guy I trust is my friend. How can I trust my boyfriend?

Q.   Im 15 and ive been dating my bf for 3 months and i have serious trust issues. Every guy ive dated has cheated on me more than once or left me for another girl then came back when he got tired of her. I dont trust my bf and i feel bad about it. I ...

A.   28 October 2010: Usually, guy friends would dislike and distrust your boyfriend by default, especially if you've had a history of choosing bad ones. If your guy friend likes this new boyfriend, odds are good that he's alright. Still, nothing's perfect, and the ... (read in full...)

Is it possible to have sexual chemistry but not like the guy as a person?

Q.   Is it possible to not like someone as a person but still be really attracted to them? I ask this as a guy friend of mine, who lets just say has a reputation AND a girlfriend of nearly a year, is to be honest a bit of a sleaze when it comes to women. ...

A.   28 October 2010: Absolutely it's possible. The traits that make women sexually attracted to a guy are different from (but not mutually exclusive with) the traits that make her like him as a person. In fact, being a player is usually a pretty good start on the ... (read in full...)

How does one deal with a commitment-phobe?

Q.   How does one deal with a commitmentphobe? I know that he more than likes me. He has proven it on many occasions over the past year. He just freaked when I mentioned the word relationship. He is still around writing, calling, caring. He took abuse ...

A.   28 October 2010: Today's world doesn't really reward guys for commiting too much, and you say he's been betrayed in the past. Guys like that are understandably slow to commit, but ultimately are much more likely to stand by those they make. It's not a phobia, ... (read in full...)

5 days ago I said something to my boyfriend that I regret and he hasn't contacted me since

Q.   A week last sunday I said something to my boyfriend which I really regret and I didnt mean. Everyone gets wound up sometimes and for me I blew and blurted it out. Well since then hes not spoken to me, ive text a few times, called and last night ...

A.   28 October 2010: I'll assume you don't really believe he's just using you for sex, or you wouldn't want him back. If that's wrong, disregard this post. This kind of accusation cuts a decent man to the core. Of course he wants sex, lots of it, but if you accuse h... (read in full...)

What kind of behavior is toxic?

Q.   I've heard people say that a guy is "toxic". Obviously i know that that's a bad thing but what would you class as toxic? What kind of behaviours etc...?...

A.   28 October 2010: Toxic behavior is the kind that makes you profoundly unhappy while being unwilling to leave. Things like a guy who stays with a physically abusive woman because he's ashamed that she hurts him, or a woman who stays with a cheating guy because ... (read in full...)

Guys! What can a girl do/wear to make your head turn?

Q.   What really impresses a guy? What will grab his attention (in a good way) and make him return that attention to you? I'm asking this to use on my boyfriend for a spark, and for future reference should I ever need it. Thanks =]...

A.   26 October 2010: Loyalty. Go out somewhere public, and no matter how many people are around or how interesting things are, pay 90% of your attention to him. If some better-looking guy hits on you, even better - introduce your boyfriend, and then pay zero attention ... (read in full...)

Her smile says one thing, her words another.

Q.   Christ, where to start... With the cliche, I suppose. There's a girl. She's not like anyone I've ever met... beautiful like a marble statue, fresh as the morning dew, funny and clever, a free thinker with more than enough brains to keep up and a...

A.   26 October 2010: I've been there, too. I've been ass over teakettle for a girl I was not dating. That way lies pain and celibacy. In the future, ask a girl out the moment you feel attraction for her (preferably before). Let your attachment build during the ... (read in full...)

Threesome lead to wife giving something that I had always wanted

Q.   Awhile back, my wife and I got drunk and lost our inhibitions and did something we always fantasized about, but should have left as a fantasy. We had a threesome, with a complete stranger. We picked a stranger, because we thought the chances of a...

A.   26 October 2010: Forget the posters blaming you for this. You get to feel upset over it. It was a pretty nasty thing of her to do. Unfortunately, it's pretty understandable on her part, and I don't think there's an easy fix. Did your wife pick the guy? If so, ... (read in full...)

After 5 years am I bored with my boyfriend?

Q.   It's been 5years, me and my boyfriend. We had argued several times about the idea of he being the giver without me sharing anything in return. I do admit my mistakes but at the same time I felt I don't deserve him. He been such a good boyfriend but ...

A.   26 October 2010: Breaking up with a person because you are bored with them sets a pretty bad pattern for your future. If you were married, would it be fair to divorce him because you were bored? You'd be hurting yourself as much as him. You need to do two things... (read in full...)

My boyfriend still thinks I'm a virgin!

Q.   Hey, I need some advice. So, I was dating this guy for about a year. Things between him and I were great, I truely loved him to death. The thing is that he asked if I was a virgin, and at the time I was. I knew that he wasn't, and he knew that I ...

A.   26 October 2010: Subtle hints will not work. Period. Just use the "No, actually I'm not" line. Use it gently, not confrontationally. He will probably be upset that you had sex with someone in the four months you were apart. Let him be upset. Obviously he do... (read in full...)

How to keep him guessing.

Q.   Girls, you know how guys say we're complex? Good news for you, they love it. Mystery is what turns a guy on the most. It's like a puzzle a game or a search, so how do you keep the search going when you are in a relationship with him? 1. During t...

A.   26 October 2010: @ SeeingStars There's a difference between being a frustrating flake and being a worthy challenge. Being a challenge means keeping up your end of the witty banter, without putting him down or leaving him to carry the entire conversation. N... (read in full...)

Is it decietful to not confess to cheating in the past?

Q.   MOD NOTE Two questions from same asker combined. Q: 1 Can someone say that they have grown and matured after they have cheated on someone, if they plan to never tell their partner they cheated on them? Can someone actually feel that they will ne...

A.   25 October 2010: Q1) It is disrespectful. You have not matured out of anything you feel the need to hide. If anything, by refusing to disclose the information, you are showing that you wish to avoid any possible consequences for your past behavior. It's childish ... (read in full...)

I don't want my sadness to be selfish!

Q.   I met my wife when i was 30, she was 39. We have spent the past 15 years in what our closest friends call the perfect love. I am, however, feeling very depressed about the timing of our love. We did not get to have children together because she had ...

A.   24 October 2010: Not selfish at all, so long as you're not blaming her - and it sounds like you aren't. It's completely alright to feel sad about opportunity costs, or about what other people's problems have done to us. Unfortunately, there's not much I can thin... (read in full...)

I just don't get it about porn!

Q.   just asking a general question most women wonder when there boyfriends look at porn do they wanna f... the porn girl or are they thinking of fucking there girlfriends? also naked pic like maxim or playboy or just naked mags. what turns them on its ...

A.   24 October 2010: Guys are visual, much more so than women. The shape of a tit is enough to get most of us going; pictures in a magazine are enough, it's just how we're wired. When we're using porn, we're not thinking about the woman, or our girlfriends. Actually... (read in full...)

Why would a woman do this to me?

Q.   I have a question for you ? I am married man who dated a divorced women on and off for 4 years. On many occasion we talked about moving in together. Until the day she told me she was pregnant and she gave me a choice of moving in with her or ...

A.   24 October 2010: She did because she could, same as any con artist. She probably never really cared about you. You displayed a lot of wisdom in asking for a paternity test, but should have followed through before you sent her a single cent. As for deservin... (read in full...)

I think one night stands are disgusting! Am I normal?

Q.   Even when I was a teenager I never beleived in 1 night stands and never had sex with a woman I didn't at least care about. I hear about so many cases of cheating, group sex and just fucking someone just for the hell of it. I find it a bit ...

A.   23 October 2010: I don't engage in them. I think they damage a person's ability to form long-term pair-bonds and have fulfilling relationships, and I want nothing to do with the drama. I'll take a relationship with a nice girl of similar values, thank you. While... (read in full...)

How to keep him guessing.

Q.   Girls, you know how guys say we're complex? Good news for you, they love it. Mystery is what turns a guy on the most. It's like a puzzle a game or a search, so how do you keep the search going when you are in a relationship with him? 1. During t...

A.   22 October 2010: 1, 2, and 3 will definitely scare away any long-term relationship guys. So if that's what you're going for, have fun in the hookup scene. 1. It's rude for a guy to ask too early, so tell him so. If you make him guess, he'll assume the farthest... (read in full...)

Getting a girlfriend

Q.   Hello I am a 17 year old male. I have never had a girlfriend before never kissed a girl nothing. Never had anyone really love me. I don't have any friends that are girls. Thing is I been talking to girls but I have not asked them out. I want to g...

A.   22 October 2010: Relax, I didn't kiss a girl until I was 18, or date until just before I turned 19. I had friends who stayed that way until their early 20's. It's not unusual or unfixable, just undesirable. While you're still in school, make some female friends.... (read in full...)

How do I prove I didn't have sex when I woke up naked next to her?

Q.   How do I prove I didn't have sex with this girl when I woke up naked next to her. I can't remember anything from the night before or the morning. the only thing I do remember is mid afternoon....

A.   22 October 2010: It's tough to prove a negative - there's no real evidence. Unless she turns up pregnant or you catch a new STD, there's no real way to know in the hours after the fact. If it helps, if you were blacked out, there's a possiblity you couldn't get... (read in full...)

What is it your partner does to keep you with her?

Q.   I'm just hoping to hear from a few long-time, happily married/committed men on what it is about their relationship with their wives/girlfriends that makes it work? Also, to any men who have/had stable relationships, what are some of the factors ...

A.   22 October 2010: Reread baddogbj's post. Every word of it is solid gold. A man certainly can be faithful forever, even if his eyes wander now and then. He just needs the right woman. Not every man can (some are just scumbags), so be sure to pick the right on... (read in full...)

Should I get pregnant knowing my fiance doesn't want another child?

Q.   My fiance and I have 3 boys (5,2,1 week), i just gave birth to a baby on 10/14. I desperately want to try for a girl and he doesn't want anymore children. 2 are his and 1 is from a previous relationship. He now wants to use condoms and get me on ...

A.   22 October 2010: Imagine if he impregnated you agianst your will, and forced you to carry the baby to term. I think there's a word for that, actually. I understand that post-partum hormones make people crazy, but that is precisely why you should not be making a... (read in full...)

Need to talk to my b/f about problems in our relationship without sounding bitchy

Q.   I'm having a talk with my boyfriend about how he has been treating me and acting and how I don't like it and etc. What are ways to do this without sounding naggy, mean, bitchy, insensitive, annoying, etc. I just want something that wont sound ac...

A.   21 October 2010: Easiest advice I can give is to re-read the last two paragraphs. Everything in them? Don't mention it to him. If you being telling him all the reasons you are stressed out before he's ready for them, he'll assume you're just there to complain... (read in full...)

My social circle thinks it's too big an age difference

Q.   Hi! I'll just jump straight in and say I've got an age gap issue that's really bugging me. I'm 21 and my boyfriend is 29 (30 in 5 weeks) and basically I'm just getting a load of flack from friends and family. I - unfortunately - come from a very Bri...

A.   20 October 2010: The age gap is fine. 29 and 21? Nothing. Don't worry about it. If anything, it means he'll still be physically very attracted to you when you're well into your forties. As for everyone's opinion of you, well, the sad thing is that certain ... (read in full...)

BF wants a Prenup...

Q.   Before I got into a relationship with my current bf, he told me that if he ever ends up with someone, he would ask for a prenup. He told me he did not want the relationship to be based on money, and that he does not have a lot himself and that tons ...

A.   20 October 2010: A prenup protects him from all the dangers of modern marriage. It's not a an insult to you; it's sensible protection from the system. Basically, in all 50 states (and, as far as I know, all of Canada), you could decide to leave for no reason at... (read in full...)

I didn't tell my online guy that I had a daughter till after we met, now he won't talk to me!

Q.   I met a guy online he was in iraq at the time.I never belived in dating sites before,it was my first time chatting with someone oline we start chatting and he was so sweet the more we chat the more I liked him,on one of our chats he asked me if I ...

A.   20 October 2010: Chalk it up to experience. I hope he comes around for you, but I doubt he will. Two things are at work here. I'll try to explain his thought process for you. The first is that you have a kid - I'm sure you know how much that hobbles a dating l... (read in full...)

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