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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...

1234567891011Next > [38 pages, 1485 answers]

Do men bond more during sex?

Q.   So me and this guy have been seeing each other for over a month now and we've been having sex consistently.So far its all going very well and he tells me how much he likes me and cares about me. Each sex session has been really intense and I can't ...

A.   10 May 2012: Guys are much less likely to make it official if you put out before you're a couple. That's true even if the sex is good, even if they like you and care about you, even if you would make an awesome girlfriend, even if you're a great person... none ... (read in full...)

Is hanging out with his friends so important, that my boyfriend cant even call me immediately when I'm crying?

Q.   Dear Cupid i had problem with office collegues on friday. I felt so depressed hence felt like talking to my bf. When i called him and after hearing his office, i couldnt control myself, hence kind of cried and sobbed and told my problem. I wa...

A.   7 May 2012: How often does this happen? If it's a one-time thing, he may not have known how to react, and just decided not to react unless you called back. Or maybe he assumed you would call him back when you were ready. If this happens all the time, he... (read in full...)

What can I say over Facebook to start a conversation with her?

Q.   hi, so basicly ther is this girl i find realy attractive who i have met once through a lass i know, basicly, what can i say to her over facebook to start a conversation? possibly get her number? that kind of thing. She is younger than me by coupl...

A.   7 May 2012: Best bet is to clear your mind of all previous interaction and start fresh. Facebook is so vague - there is no qualitative difference between an acquaintance casually Liking an occasional status and a desperate secret admirer carefully rationing ... (read in full...)

Is moaning during kissing normal?

Q.   Just a simple question..... i was going out with this guy and well he took me to the movies and dinner but then when he drove me home we started kissing and well as were maaking out he was moaning i thought it was wierd. We had only been tpgether ...

A.   7 May 2012: Depends on how much he was moaning. A bit is normal; if he's moaning a lot, he may just be inexperienced and is doing it because he thinks he's supposed to.... (read in full...)

Will girls be repulsed by my body ?

Q.   I am 15 and i have never had a girlfriend, all of my other friends have had girlfriends and most of them have had sex. If i get a girlfriend i am kind of afraid of sex because i am slightly fat. I am 5"4 and i weigh 10.6 stone. My BMI is 25.5 which ...

A.   7 May 2012: On the one hand, your body will work against you in initial attraction; however, girls pay attention to these things - so it won't be any surprise to her. She'll have noticed it just seeing you move around every day. If she decides to get intimate ... (read in full...)

Short term relationships: What does porn and experience do to girls' perceptions of sex and penis size?

Q.   I get the impression here that this site is mostly about longer term relationships, but I would like to ask something about the purely sexual side of things because I'm certain that a large percentage of girls LOVE sex and will have sex (sex buddy, ...

A.   4 May 2012: 1) The visuals in porn have a larger effect on men than they do in women. A girl's ability to be satisfied with a guy is much more likely to be negatively affected by Hollywood depictions of reckless, angsty, perfect alpha males than it is by ... (read in full...)

Are men put off by women who have given birth?

Q.   question for the men on here.. Are men put off by women who have given birth? either because they watched their partner give birth which has put them off sex and can't get the image of their head of seeing partner being stretched and watching som...

A.   4 May 2012: Some men, yeah, but I wouldn't put a number on that except to say its probably a minority. I can't find it right now, but I recall a study some years back that showed some men had a hard time seeing their wives sexually after seeing them give ... (read in full...)

Is it true men love stockings and suspenders?

Q.   Hi everyone I just need to ask a quick question I am planning on surprising my boyfriend. Is it true that men love stockings and suspenders? I just need some answers as I am unsure whether he would like it or not thank you ...

A.   1 May 2012: Not all men are into that, but *all* men are into a girlfriend who tries her hardest to please him. Ultimately, that's what every male fantasy boils down to - this woman wants him bad enough to work for it. Get the stockings and have some fun... (read in full...)

My girlfriend had violent ex and she slapped me last night. Is she into that?

Q.   I have a wonderful girlfriend- we get along super well and even though we have disagrements, we never fight and have a great chemistry. A few years ago, she came out of a bad relationship where the guy she was with would insult her, call her 's...

A.   28 April 2012: I think she's into the dominance of it. Slapping is just a manifestation of that (really, rough sex isn't so bad); the core is dominance and passion. Either she likes to be more in control during sex, or she wants to challenge you to be more ... (read in full...)

Why hasn't he asked me to be his girlfriend yet?

Q.   i have been dating a great guy for 2 months now and we agreed to only see each other, but he has never asked me to be his girlfriend. could this be because he thinks it is still too soon? or maybe he isnt over his ex, who he broke up with at ...

A.   27 April 2012: Depends. If you're already sleeping with him without being official, it's because of that. If you're not sleeping with him, it's because he still needs some time to figure out if you're really the type to commit for a long while, or if you're the ... (read in full...)

Was I being a pushover by agreeing to my friend's demands?

Q.   I've had my best friend for about 5 years. He's a dude and I'm a chick but we have a really siblingish friendship, we're the same age and we often tell each other everything. But recently he's been kind of selfish and insensitive. ...

A.   27 April 2012: People don't often understand the effort that goes into a craft. That goes double for when they're proud of a friend who can do it. I'm an engineer, and occasionally friends will want me to do things that are way beyond my expertise (install a ... (read in full...)

I didn't trust him and tested him and now I've lost him!

Q.   Dear friend, I feel quite sad in this two weeks, Iam craying every single moment , guess why!! It.s have been 5 months that I am in relationship with a lovely man, I think now clearly I am in love with him, but In last two weeks I think I made a b...

A.   27 April 2012: Do you know for certain that he was chatting with other women online, or are you just guessing? Is it possible he was just chatting with friends? Maybe with male friends? Do you know why he was not on the camera? I am not certain how you test... (read in full...)

Why did my father-in-law have no empathy when I revealed the extent of his son's infidelities?

Q.   I was wondering if anyone could give me some insight or thoughts on the reaction of my in-laws (particularly father-in-law)when I revealed to them, when I was extremely upset, about the extent of their son's (my husband), cheating on me over a 6 ...

A.   27 April 2012: I can think of two possibilities. They may have said something, and you may just not be in the loop. Obviously, this is pure speculation, but among male friends and family, there is kind of a "front" put up for the women. To a certain extent, ... (read in full...)

How do you keep an older man interested?

Q.   So I just started dating this older guy, he's 26 and I'm 18. Does anyone have any advice on how to keep an older guy interested? ...

A.   24 April 2012: He's not really that much older - my own parents are eight years apart. Still, the key is the same as with any guy - be loyal, be pleasant, and be humble. Don't be rude, don't be stupid, and don't be a doormat. Maybe you're already doing these ... (read in full...)

How do I distingush whether he likes me or just likes to have sex?

Q.   I started to date a guy and wish to have a serious long term relationship. If the guy want to have sex with me? How do i distingush whether he like me or just like to have sex? How long or how many dates should have before the intimacy? thanks an...

A.   24 April 2012: Men in their 30's and 40's are not usually as willing to wait very long for sex, even if they are serious. To them, it smacks of game-playing, and they got tired of games in their 20's. After all, for every player who is only out for sex, there is ... (read in full...)

Am I right to be upset?

Q.   Dear Agony Aunts and Uncles, I really need your advice because this situation is really, really upsetting me/ making me nervous. You see, my boyfriend and I have been together for nine months and I've known him for a year, at least. He is a v...

A.   24 April 2012: He didn't tell you because he thought hearing the truth would make you upset. Now that he's told you... you're upset. I'm right there with him. There's a 50% divorce rate - you don't think that half of all couples walk to the altar and say, "Ye... (read in full...)

Just in honor of world peace.

Q.   I've had an absence since 2010, I know, it's been a while, but I'm coming back just to help out with anyone, it doesn't have to be based on just relationship trouble either. So I apologize if that's what you're looking for in this article, these are ...

A.   17 April 2012: Quite an article. I'll throw down a few thoughts - some hopeful, some not, but at least an attempt to give you something to think about. "Each person says that they will make a difference, a change, but it is only said for publicity, it’s not... (read in full...)

How can you sustain a romantic relationship when the guy isn't into your looks, or is only attracted to you based on your personality?

Q.   I've never been much of a romantic; I don't really believe in love at first sight, or soul mates, and far prefer my relationship to be based on practical criteria over emotions (we have common interests, we have good conversations, we have a similar ...

A.   17 April 2012: Lust at first sight is not something everyone experiences. Don't worry about that. But if you want him to look at you with lust right now? Make yourself look the best you can - get a gym membership, eat healthy (and do research, a lot of common ... (read in full...)

Should I be an asshole to get girls? Or be the nice guy? Or just give up and save myself the hassle?

Q.   Im 19 and have aspbergers disorder (autism). tragicly for me, im a super nice guy. I dont think im ugly or that it had to do with my looks sense ive seen way gnarly looking asshole guys get handful's of women. I want to know if its better to be...

A.   17 April 2012: I think there's a language barrier between you and some of the comments here. I've lately realized that a lot of nice guys say "only assholes get women," but that a nice guy's definition of "asshole" is pretty vanilla. Am I correct in guessing ... (read in full...)

Men & Women: How long have you gone without sex?

Q.   How long have you gone without sex with another person? ...

A.   9 April 2012: A little over two years, after my first girlfriend and I broke up when I was 19. I remember feeling really insecure about it, and eventually giving up on my conviction about random sex outside of relationships... then, before following through with ... (read in full...)

Why do guys find flexible girls sexy?

Q.   Why do guys find it sexy if a girl can do the splits or can wrap their legs around their neck, basically be flexible?...

A.   16 March 2012: You can try all sorts of new things, like running your hand up and down her (probably very shapely) legs and her boobs at the same time. It also presents her ass very nicely when she puts her legs behind her head. Or, she could ride cowgirl-style, ... (read in full...)

I want to have a relationship--but I find women utterly annoying!!

Q.   ok here's my problem. i've never really had a successful relationship with a woman. the reason is...the ones I've dated or known closely have gotten to be the most annoying, superficial. dishonest, and gossipy individuals I've ever met. i am ...

A.   15 March 2012: Welcome to America, have fun with that can of worms. I'll start with the obligatory: there are lots of bad men out there, too (women hardly have a monopoly on dishonesty and shallow wastes of money). And there are good women. There, now I can fo... (read in full...)

I feel like I'm a bad wife because I don't like giving him blowjobs, what can I do to stop being disgusted by them?

Q.   Hi, Im 24 years old and newly married for 9 months. Our sex life has been great except that my husband really likes for me to give him blow jobs, but no matter how hard i try i feel disgusted to do so.I think the taste/smell is what puts me off.I ...

A.   15 March 2012: The taste is one thing, but if the smell is bad, he needs to work on his hygiene. Have him trim his pubes and scrub that area better, then blow him right after a shower so he hasn't had time to get all sweaty. You'd be surprised how often men ... (read in full...)

How do I approach my girlfriend's weight issue?

Q.   In the 3 years we have been together my GF has been slowly letting herself go physically to the point where I no longer find her attractive. When we met in college, she was more physically active on a daily basis but now she has an office job wh...

A.   15 March 2012: The best thing to do would be to just accept that there is going to be a fight, and that bringing it up in any way is going to result in much wailing and gnashing of teeth. Be prepared to weather the storm before she'll change. Confront her abou... (read in full...)

Is it normal for boyfriends to complain to friends about you?

Q.   Is it normal for your boyfriend to complain about you to a friend? Do the circumstances matter? I know that I've discussed concerns I have about my boyfriend or about our relationship to friends, but because ultimately I believe my boyfriend is ...

A.   15 March 2012: It's normal. I don't think it's healthy for the relationship, or even for the individual doing the complaining, so I really don't recommend it, but so many people do it that it definitely counts as "normal." Guys tend to complain about girlfrie... (read in full...)

Without being engaged, does that mean that the long-term feelings aren't there?

Q.   I've been with my boyfriend for a little over a year, and one of my friends asked me why I wasn't planning on getting married with him anytime soon. I told her I wasn't ready to get married necessarily anytime soon, but she then asked why I wasn't ...

A.   15 March 2012: Don't listen to your friend. I'll bet she's the same friend who would get you worried about a wedding date once you were engaged, then worry you about children once you're married, then worry you about divorce once you've been with him three or ... (read in full...)

Can 13 year-olds find a lasting relationship, or is this just puppy love?

Q.   Ok... know a lot of you will disagree with my view on this but oh well...I'm 13, and I have a boyfriend of 8 months, we really get along and we have almost everything in common, he told me he loved me and I told him I loved him too but then i felt ...

A.   14 March 2012: Normally, I'm all about knowing the likelihood of things working out (I'm a numbers guy; I like statistics), but in this case? I don't think it does any good to worry about it. If you really want to know, I don't think it'll work out, but the real ... (read in full...)

Married women: what could your hubby do to rekindle the fire of your attraction and affection?

Q.   A question for the married women: what could your husband do to spark a fire of romance, excitement, strong feelings of love or attachment? I feel like my wife is drifting away. What things can I do to rekindle her interest, return that warm glow ...

A.   14 March 2012: Well, it's one of two things. Women are attracted to men in two different ways (actually, the same is true in reverse - you're attracted to women in one way when they're sweet, feminine, and sensual; you're attracted in another when they're ... (read in full...)

How do I tell b/f in a nice way that I'm horny and want more sex?

Q.   My bf and I have been together 8 months. We met on a dating site. He still lives with his parents (for various reasons) and since they are an hour away from me, he basically lives with me 3 nights a week on the weekend. The problem is that, on ...

A.   13 March 2012: Foreplay starts when you wake up, not when you first get horny. Flirt and get a little touchy early on, and stay that way all day. Give him a five or ten second kiss in the early morning when you first see him. Wear something a little sexy in the ... (read in full...)

What's the Best Way to Deal With my Wife's Conflict With Other Women in her "Social Group"??

Q.   My wife moved to the U.S. from the Philippines about 10 years ago, and we've been married a couple years. She's in her mid 30s. She recently had a falling out with one of her Filipina "friends", and both of them seem to be escalating the s...

A.   13 March 2012: This is one of those things where eventually, no matter what you do, it's going to lead to a fight with your wife. The question is when and how you want that to happen. Women want drama. How much they want depends on the woman, but they all want... (read in full...)

Could my baby look like my lover?

Q.   If a woman is pregnant and sleeps with another man can the baby have features of the man who is not the father?...

A.   21 February 2012: What is this... why... I don't even... Look, Miamine is exactly right, things like this are why guys like me are (and will continue to be) so harshly critical of promiscuous women. No, your baby will have no resemblance to the non-father unles... (read in full...)

Why am I having so much trouble dating?

Q.   Hi I'm 16 and for some odd reason I can't get a girlfriend I have good grades I'm not a nerd I play football I try asking them out and the always say "no" or "I'm not ready" then like a few weeks later there dateing someone else and or if they are ...

A.   21 February 2012: Because what girls want most (especially at your age) is a man with social savvy and too much confidence. Good grades or bad, doesn't mean a thing to them (but keep up your studies anyway). Football is only one facet of the confidence and social ... (read in full...)

Why does my G/f defend her horrible, abusive ex every time I say something negative about him?

Q.   This is my problem. I have been with this woman for over two years now. I love her very much. When we first met everything was going well. Shes been in a abusive relationship for nine years with her ex. She told me how he cheated on her multiple ...

A.   13 February 2012: She does it for the same reason that she stayed with him through so much abuse - that sort of behavior has a very primal appeal to a certain subset of women, and she's probably part of that subset. It's evolution in action. We can all agree th... (read in full...)

My height has grown and I'm too slim. How can I put on weight in healthy way?

Q.   I am too slim how I can put weight ? Have muscles?my height has grown very well but I am very slim.....plz help here..I am new here...

A.   13 February 2012: Just to add something to my post below - those numbers are for men. I don't know how fast women can expect to gain or lose muscle and fat, so for any female readers just looking for info, you'll want to do your own research. The difference in ... (read in full...)

Guys if you found out your girl was an older virgin would it be a deal-breaker?

Q.   Guys, if you found out that the girl you liked was still a virgin would this make you more interested in her, or would it be a deal breaker? If she's an older virgin at that....

A.   13 February 2012: Not a deal breaker for me. I'd want to know a few details, but that's also true for any woman with any history if I'm dating her seriously.... (read in full...)

My height has grown and I'm too slim. How can I put on weight in healthy way?

Q.   I am too slim how I can put weight ? Have muscles?my height has grown very well but I am very slim.....plz help here..I am new here...

A.   13 February 2012: Weight is easy to control, but it takes patience. To gain weight, just eat more calories than you use in a day. To gain healthy weight, eat healthy foods and exercise - but remember that if you exercise, you will be using more calories, so you ... (read in full...)

How can you tell if you're a good kisser?

Q.   hiya. Right, this may sound a little awkward and slightly weird but I'm with my 3rd boyfriend and it's only with him that I've kissed. Thing is, i'm afraid to ask him if its ok because I don't know how your supposed to kiss. I think I'v been rea...

A.   13 February 2012: You're not born magically knowing this stuff. Don't worry about it, and don't feel insecure - anyone who knows how to be a good kisser learned through practice (actually, that's true about a lot of things in life). You weren't born knowing how to ... (read in full...)

Is too much sex bad for my relationship?

Q.   I have been with my boyfriend for 3 years and we have shared a brilliant and adventurous sex life. I have a very high sex drive and he has always been able to keep up until recently he is turning me down more and more. I initiate the sex I'd say 4 ...

A.   6 February 2012: Olderthandirt's got it right. I've yet to meet the girl with a sex drive I can't keep up with, but anything could happen. Wouldn't want to speculate on how I'd react (what we think we'd do is all too often different from what we actually do), so ... (read in full...)

I regret being so shallow about a guy's height

Q.   I turned down an opportunity to be with a guy who was committed and a good person.  The main reason I walked away because of his height. He is 5 ft. I am the same height and petite. All I can think about is the life we could have had together. Bu...

A.   6 February 2012: It's not shallow. Shallow would be dating someone you're not attracted to because you feel like you "should," or because you'd rather date anyone than be single. You owe it to whoever you're with to be with them because you are attracted to them, ... (read in full...)

Am I being silly because I am worried about him seeing those girls?

Q.   i'm meeting this guy tomorrow, we met one night out and now we've arranged to meet again in a club/bar because then it's more of a relaxed environment and we'll be out with our friends making it less awkward and meaning we don't have to stay ...

A.   6 February 2012: What if it does go wrong? What if he does end up liking someone else, or you get attached and he doesn't? Well, life goes on. You'll survive it. But I think you're seriously overestimating the chances of that happening. Don't get me wrong, i... (read in full...)

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