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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...

< Prev1516171819202122232425Next > [38 pages, 1485 answers]

He's asking me what I want in the bedroom and I don't know what to say!

Q.   -I've been with my boyfriend for 4 months. -We are very private so none of our friends know about us. -I lost my virginity to him, therefore am not very experienced in the bedroom -We are both of legal age (me 18, him 20) So we wer...

A.   14 January 2011: Just try things. By definition, half of all sex is going to be below average. And you'll be lucky if only one out of every four or five things you try in bed is mutually appealing. So, let the pressure off, try whatever comes to mind. If it ... (read in full...)

I don't know why I can't get a man!

Q.   Although many people say I am attractive (not young) I dont know why I cant get a man. I meet meen who would like a "fling" as "they already have a partner I meet men who say "You must have slippedd through the net someone should have snapped me ...

A.   14 January 2011: @ OP "WHY is it easier for guys to get laid now than before? Hasnt easy sex always been available???" Depends on the guy. This is what's called the "apex fallacy." It's easy to look at just the best examples, and conclude that everyone mu... (read in full...)

What 'unknown' condition could it be that stops a girl from having sex?

Q.   I was recently speaking to my girlfriend about sex, and she kind of let slip that she 'until recently' couldn't actually have sex because of a medical condition. She said only that is was apparently not that rare, and now it is fine (presumably ...

A.   13 January 2011: Any number of infections could do it - and not just sexually transmitted ones. She could have sat on a dirty toilet seat, for instance. Those can be cured, for the most part, so if she says it's gone, it probably is. If you're concerne... (read in full...)

How do I attract the bad boys?

Q.   what is it abour me that attracts unattractive guys i mean my mom always told me to be nice so i am and i attract boys who i dont like how do i get the ones wh i like what do i do.ps i like the bad boys...

A.   13 January 2011: I'm not sure I understood your followup, so I apologize in advance if I'm not answering the questions correctly. If you're physically unattracted to the kind of guys who are attracted to you, it's one of two things. Either you are less attracti... (read in full...)

Is it possible for a woman to cry on demand?

Q.   Hi, Last year I was in a relationship with a woman who in retrospect I feel was manipulating me. She had asked me for a lot of money and I gave it to her over the course of the year, without getting anything back. (We were not even dating.) But I fo...

A.   12 January 2011: It's called "crocodile tears," and should be met with scorn and mockery. Many women can cry on demand (some guys, too, like my old roommate, but that's a somewhat less useful skill for us). Real tears should be met with care, but that doesn't ... (read in full...)

How do you formalize a breakup without a lawyer?

Q.   Section breaking up. Hello, I wanna break up with my gfriend for cheating, but I would like to avoid going to a lawyer. We have a 2 year old. I figure if I pay for: 100% the apartment they live in including utilities 50% the kinder garden...

A.   12 January 2011: Research mediators, and find one who has a reputation for being fair to men. Try to get binding mediation - you're looking for closure, not suggestions. I'd suggest offering less than you are willing to pay, the bare minimum that you can call "fa... (read in full...)

My wife thinks I messed up, but I don't think it's a big deal.

Q.   I need some advice. My wife thinks I messed up, and I think that what I did was no big deal. I was out with a bunch of work people after work. I occasionally take my team out for after work drinks/appetizers when we make a project goal. Th...

A.   12 January 2011: What you did was wrong, but it's an easy mistake to make. Leaving aside the complete and blatant disregard your co-workers showed for propriety, as a guy you should know that it's never, ever going to fly talking to female co-workers about sexual ... (read in full...)

I don't know why I can't get a man!

Q.   Although many people say I am attractive (not young) I dont know why I cant get a man. I meet meen who would like a "fling" as "they already have a partner I meet men who say "You must have slippedd through the net someone should have snapped me ...

A.   11 January 2011: Hopefully you'll come back and check this; I know it's an old question, but saw it in the list and figured I'd take a stab at it. First, I'll try to answer the "why." It's because 90% of single women over fifty want a relationship, and 90% of s... (read in full...)

Why is it okay for bigger women to bash slim women, but not the other way around?

Q.   This is something I notice a lot, and I find it very insulting. I've always been slim, naturaly slim. I have never dieted or watched my weight and I'm a healthy size 8. It seems that if a slim girl is ever to speak bad of a fat girl, they are given ...

A.   11 January 2011: Because, just like it's easier to be fat than healthy, it's easier to be mean than nice. It's easier to pull someone down to your level than to uplift yourself. And all social interactions takes place at the lowest common denominator - that is, ... (read in full...)

My boyfriend won't propose, he comes up with lame excuses!

Q.   I've been with my boyfriend for 5 years now and we've lived together for 4 of those years. He won't propose and comes up with lame excuses. The thought of starting all over with someone else stinks but I'm tired of his excuses. Should I stay or ...

A.   11 January 2011: Think of it from his perspective. To you, it sounds like he has just lame excuses; to him, the only reason you want to get married is "just because." Making the relationship contingent on a wedding will make him feel less like a person and more... (read in full...)

What are the long-term emotional/psychological effects of a promiscuous lifestyle?

Q.   I know a girl who I am friends with, sort of. She is very loose sexually and frequently has sex with men for money. She had an affair with a married man a few months ago but I think she broke it off when it became clear this man was not leaving his ...

A.   10 January 2011: Promiscuity is habit-forming (this goes for both men and women). The hormones released during sex are intended to create bonding. Ignoring that bonding feeling causes serious emotional harm crippling the ability to form real relationships. On the ... (read in full...)

Why are men players?

Q.   Why are men Players??? Why do they have a daytime girl and a nite time girl?? ...

A.   10 January 2011: It's mathematically impossible for us to be that way, unless we're all sharing women. Only a fraction of men do that - oddly enough, the fraction that gets multiple women overlaps with the guys women want most... Cerberus is absolutely corre... (read in full...)

He says I am his second 'conscious', what does this mean?

Q.   When a guy says your his second conscious what does that mean?....i have been friends with a guy who i like and he like me but we havent spoke about a relationship are we just friends or he just wants to take things slow? We indeed had sex but i ...

A.   10 January 2011: You sure he didn't say "Conscience?" If so, he thinks of you as a good person who inspires him to be a better man. That, or he meant "Consciousness," meaning you do his thinking for him. I think the first is more likely. If you've had s... (read in full...)

Am I weird for wanting to marry the only man I've ever dated?

Q.   Hi, I'm a woman, 23 years old, and I have only dated one man seriously in my life. He's my boyfriend at the moment, and we've been together since I was 17 (yeah, first real bf at 17, I was a late bloomer!) He loves me and wants to marry me, ...

A.   9 January 2011: Not the least bit weird. You ljust got lucky. You've clearly realized that relationships take work, but are worthwhile - without having to throw away good ones to do that. You'll be better able to bond with this man for not having spent your you... (read in full...)

What is this respect thing about?

Q.   I have been dating a guy for a while now. We sat down to have a talk because things are not going so hot. I have always been supportive and warm towards him. During the conversation he said that I would have to earn his respect and he did not trust ...

A.   9 January 2011: This is the attitude that punk teenagers have - "Earn my respect before I give it to you." People deserve respect by the mere virtue of being human beings with thoughts and feelings of their own. Not to mention, why should anyone want respect ... (read in full...)

An animal in bed?

Q.   When a guy says, "She's an animal in bed". What does that mean? I'm not into rough sex or anything, but the expression always puts me off a little. ...

A.   9 January 2011: It's a compliment. Guys use different words than chicks to describe good things. Nothing wrong with that - chicks may use "dreamy" as a sincere compliment, but no guy will ever do so. Just different languages. In this context, it means a girl w... (read in full...)

Why would he masturbate when he has his wife?

Q.   I periodically find used condoms in my husbands things. Like in the bathroom under a towel, or this week in his bathrobe. I know he is masturbating in them, but what should I do?? When I was first married I called him screaming and crying thinking ...

A.   9 January 2011: Men whack off. It really has nothing to do with how satisfying their love life is or isn't. It's more like scratching an itch than anything else. Seriously, telling a guy not to masturbate is like a telling a woman to ignore the smell in the ... (read in full...)

Why can't I get past a 3rd date?

Q.   I have been trying to date for a good 6 years now and no one has ever showed an interest in staying with me past a third date or so. I am 28 years old and have been rated an "8" on a looks scale from 1-10. I make close to 6 figures in a good ...

A.   8 January 2011: First, dating abroad would be a great experience for you. Enjoy it. Second, American women want strong, assertive, confident, dominant, masculine guys who don't put up with their nonsense. They want men with options - that is, guys who can leav... (read in full...)

How can I become a born again virgin

Q.   How do I become a born again virgin I've been with a lot of guys and I'm now really starting to regret it I really want to change but I don't know how to make it official ? Can someone help me please?...

A.   8 January 2011: It's commendable that you want to turn over a new leaf. So, my compliments on that. But fair warning, it's not going to make every problem go away. Born-again virgins are women who have accepted Christ as their personal lord and savior, and swor... (read in full...)

I want to have sex so I won't be the only virgin

Q.   So I'm 16 and a half and junior in high school. I'm a virgin and this fact hasnt really bothered me really. Now im finding out that alot of my friends are having sex or doing other sexual things with either their girl friends or random chicks. I ...

A.   8 January 2011: You're not the only one. There's a selection bias. Do you think the guys *not* getting laid are bragging about that? They're either keeping quiet, or pretending they have had sex. You should take anything you hear about an "out of school ... (read in full...)

How long is long enough to expect commitment when you are sleeping with a guy??

Q.   I began dating this guy about 2.5 months ago. I had just gotten out of a short term relationship, and before that had a baby and was in a long term before that. He had just gotten out of a divorce a year ago, and the night we first "hooked up...

A.   8 January 2011: In this case, it's not a matter of too fast or too slow, it's a failure to be clear. To a guy, the contrast between your words and actions would have been confusing. The first mistake was when you told him you did not want to be FWB because ... (read in full...)

Do men ever regret leaving a woman pregnant and alone?

Q.   A question to all males out there or females in my situation. do men ever regret leaving a woman pregnant and alone? my ex boyfriend left me pregnant and alone, we live in different countries and he has never met his son (4 months old). when i was ...

A.   7 January 2011: I think part of the issue is that you believed it was his job to support you and be there for you. He was your boyfriend, not your husband. And you knew he lived in another country. The vast majority of men are decent folk, not monsters... (read in full...)

What should I do with a boyfriend who is so loving and supportive that I can't reciprocate?

Q.   I am in a ridiculous predicament - my boyfriend is a wonderful guy to me, he will do anything to please me. Of course he has his negatives (as does everyone) but he is just so caring, supportive and loving to me... yet I just can't reciprocate. I ...

A.   7 January 2011: You're facing the classic female dillema of loving the attention and devotion from a nice guy, while craving the excitement and unpredictability of a bad boy. The fact that he shows you that he cares is actually making him a sure thing, and it's... (read in full...)

Do guys like their hair being played with?

Q.   Do guys like to have there hair played with? Not just when kissing...

A.   7 January 2011: I used to have really long hair. Never liked it being played with. Now I have short hair, same story. I like a girl's hands on my head, or most any other place for that matter. But if it's not a prelude to sex (or at least really, really s... (read in full...)

Real love can never happen unless you can trust, give, and communicate

Q.   You are at work palms all sweaty thinking about tonight and part of you wants to just say,"forget it." Everyday you are falling for him and you know where this is leading. You want so bad to make this work but your past is holding you back. When ...

A.   7 January 2011: @ OP Revealing everything early on would certainly save time (assuming we could do that without scaring people off just by open we are; as a guy, I'll tell you that chicks respond better to mystery than openness). My contention is that, once ev... (read in full...)

Do men ever regret leaving a woman pregnant and alone?

Q.   A question to all males out there or females in my situation. do men ever regret leaving a woman pregnant and alone? my ex boyfriend left me pregnant and alone, we live in different countries and he has never met his son (4 months old). when i was ...

A.   6 January 2011: It really depends on whether the kid was an accident or not. Or an "accident." Granted, some people are just sociopaths, there's no accounting for them. The vast majority of men would feel guilty about leaving a woman who had a kid they had mutu... (read in full...)

Ladies, how do I make it known that I want sex with this woman?

Q.   At a dude ranch last summer I met a attractive woman. We had fun during the time at the dude ranch. At the ranch we did a lot of things together. Before leaving the ranch we even had sex. We had a good time in bed. Since going we have stayed in ...

A.   6 January 2011: Bring a bottle of wine, not lingerie, you don't know her well enough for that. It will turn her off. I know you've been staying in touch, but you've only slept together once or a few times, and that's what counts here. Plus, you can drink the ... (read in full...)

What do men think about short women?

Q.   What do men think about short women? Are they cuter than a girl that's of average height? I'm really into this girl that's 5 ft. I'm 6 ft 3 and she always jokes that I'm a giant compared to her. I don't think our height difference is a problem, but ...

A.   6 January 2011: I likes me some short girls. You can lift them up for kissing, or stand on the lower side of a step, and sex with them isn't really as much of a problem as you'd think. Have fun!... (read in full...)

Guy with definite mixed signals!

Q.   I like this guy who is very much a ladies man! he has never admitted he likes me but gets with me sometimes and texts me quite a lot, I know he talks to other girls so it isn't just me but I know all he wants is sex because thats what he tells me ...

A.   6 January 2011: Players know exactly what to say to make girls swoon. Mixed signals are the single best way of getting a girl hot and bothered, so on the one hand he tells you the truth (he only wants sex), and on the other he hints that he likes you (he ... (read in full...)

Real love can never happen unless you can trust, give, and communicate

Q.   You are at work palms all sweaty thinking about tonight and part of you wants to just say,"forget it." Everyday you are falling for him and you know where this is leading. You want so bad to make this work but your past is holding you back. When ...

A.   5 January 2011: I get where this is coming from. It's heartfelt and compassionate. Still, I take issue with this one part: "Wouldn't it be wonderful if you could reveal everything about yourself and the person you love would still be standing there. Real lov... (read in full...)

I love you? versus I'm in love with you...hmmm

Q.   Hello, I was wondering, my soon to be hubby says "I love you" and I love him too, but is there a difference between saying "I love you" versus "I'm in love with you"? Don't get me wrong, but we both love each other, however, I was told by a gf tha...

A.   5 January 2011: The only time men even notice the difference is when women say, "I love you, but I'm not in love with you," which guys view as a B.S. excuse anyway. In other words, doom and gloom. Don't worry about the distinction unless you're splittin... (read in full...)

If a guy likes girl, why does he ignore her?

Q.   ok if you guys like a girl why do you ignore her and treat her like shit and not return her texts then act like nothing happens a month later...

A.   5 January 2011: There could be plenty of reasons, depending on the context. I can give you two that I consider likely, but there are a number of other possibilities. If you post more info in a follow-up, I'll be happy to refine my guess. First reason is, if h... (read in full...)

Friend's cheating boyfriend, could he give her an STD?

Q.   A friend of mine and I were debating over STD's. Her boyfriend has been cheating on her with at least 5 other women repeatedly, as well as still having sex with her. Although they've all been tested (her, her bf, and his other girls) , a differen...

A.   5 January 2011: Have you or your friend actually seen the official test results? STD's are embarassing, and a lot of people will lie about being tested - cheating boyfriends and loose women in particular. I'd be willing to bet good money at least one of them just ... (read in full...)

Am I turning him off or is it his ego?

Q.   i like a guy at school hes in 8th grade imin 7th and we talk sorta and have conversations.so heres my problem i like him a lot but i dont know if im turning him off. before we were at the park and we were talking and he seemed really intrested i ...

A.   5 January 2011: His ego would have nothing to do with whether he stops talking to you. A lot of guys act like they have bigger egos than they really do, especially at that age, so your friend's assessment could be off. Without knowing what was specifically said, ... (read in full...)

How do I attract the bad boys?

Q.   what is it abour me that attracts unattractive guys i mean my mom always told me to be nice so i am and i attract boys who i dont like how do i get the ones wh i like what do i do.ps i like the bad boys...

A.   5 January 2011: To attract bad boys for sex, just offer sex to the guys you like. Seriously, they'll take you up for it. You cannot hope to attract bad boys for a relationship - at least, not for one they'll be faithful to. At best they'll pretend to care lon... (read in full...)

When guys ask women about their sexual pasts, do they really want an honest answer?

Q.   This question seems like a no-brainer at first... who's going to say they DON'T want honesty? But then I read all the posts on here from people (mainly guys, it seems) who are insecure about what their partners have done before them, and with whom, ...

A.   4 January 2011: If a guy doesn't want to know, he doesn't ask. If he asks, it's because he's trying to gauge your long-term worth. If the number is too high, or includes too much meaningless sex, or includes the sort of people he doesn't approve of, he'll decide ... (read in full...)

Relationships: An Observational Assumption

Q.   I was revising physics when an epiphany struck me that made me realize something potentially significant about the high rates of failure in cross-gender relationships, that is male and female companionship( and if you're wondering what the ...

A.   4 January 2011: While putting the chance of permeability at near zero is off by about fifty percent these days, I'd say ChiGirl is right: you've caught on to what marriage was invented for. It was not meant to be a declaration of love - many old cultures wisely b... (read in full...)

Why do women so often go back to their abusers?

Q.   Why are some women so stupid? Not trying to be sexist, trust me, this is why I said SOME women. Let me define, specifically women that will remain trapped in an abusive relationship, not only once, but then walk right back into it thinking it's...

A.   4 January 2011: Women run back to their abusers because of old, old instincts driving them to try to secure the protection and genes of strong, aggressive, dominant males. Their offspring will be more likely to be successful that way, at least in the ancestral ... (read in full...)

What has gotten into my wife?

Q.   Ok, Not sure what has gotten into my wife, have had a strange New Year thus far. Anyhow, leading up to the New Year she is making her resolution list and out of the blue comes up with an idea and leaves the room to write her thought down, me...

A.   4 January 2011: I think the important part of it is this - "...avoided the argument, but it kept going and going. Well, I restrained myself pretty good, while not becoming a pushover at the same time. The passion actually carried over to sex." Rather than arg... (read in full...)

I have a disfiguring condition. Will he stay with me?

Q.   I feel so confused... Iv been with my boyfriend for 6 years now, and he was my first love, i was his. It feels so right and we both are very much in love. We started dating from when we were at school, i was always quite shy and he was loud..and ...

A.   4 January 2011: I can't say what he'll do. Some people will be supportive for a little while, then leave (there was a similar but gender-flipped question a while back suggesting that). What I can do is tell you about a friend of mine. This girl, call her Alic... (read in full...)

Why do guys run when you mention "baby"?

Q.   i going to be giving birth in the next month and the father who i was dating for, for 6 years did a legger as soon as i told him he has a new gf now anyways i have to do it all on my own to be honest i don't think i'm ready to be a mam or to do it ...

A.   3 January 2011: Guys do that when they didn't plan to have a baby. Especially younger guys - fewer of them have been raised to believe in the obligations of a father, and even those that have see no benefit in doing so. I didn't see anything in this question... (read in full...)

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