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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...

< Prev1718192021222324252627Next > [38 pages, 1485 answers]

I cant get over my wife's past!

Q.   Hi all, please help me in this issue, i hate the partner/lovers changing girls, I had no girl friend or sex in life, i used to watch a girl but no use, now i m arranged married person but after few years i came to know my wife had 2 bfs but not sex ...

A.   21 December 2010: Hey, could be worse. You could live in America. Here, the concern would be that she's slept with five, ten, twenty guys (or more) before us, instead of just having dated two guys. Not even counting single mothers, STD's, or "technical virgins." ... (read in full...)

We're both attached so why does she act this way?

Q.   So Here goes. I have been working with a very nice pretty lady for 3 years now. I am married. She got engaged a month ago. When I first started working with her she was single and I had a strong sense that she was attracted to me. She would touch my ...

A.   21 December 2010: A lot of women are more attracted to guys in relationships. Others like to cheat right before they settle down, believing it "doesn't count." She sounds like an intersection of the two. When only one of those conditions applied, she was more com... (read in full...)

I'm not ok with him hanging around with women he's slept with!

Q.   Ok I'm not comfortable with a situation I'm in and im not sure how to address it.. To keep it simple..prior to my relationship, my bf racked up a large 'score' so to speak.. and he's from a small town so everytime he goes 'home' he's around or p...

A.   21 December 2010: Promiscuity is habit-forming. If he is continually exposed to opportunities to cheat, especially when he goes home and has the nostalgia filter workign for him, he's going to be continually tempted. He has already demonstrated that temptati... (read in full...)

I want that inch back! Does weight affect penis size?

Q.   I know this is kinda of weird question. Well like a year ago i had 9 inch penis but i was 6.5 tall and had only 160 pounds. So i started to work out and gain weight well i am 210 punds now and my body is in a pretty good shape ,but my penis seem to ...

A.   21 December 2010: Weight does affect penis size. It's pretty much "rooted" to the same part of your internal anatomy no matter how much you weigh. So, add enough weight in the form of muscle and fat to the outside of your body, and some of that is going to be in ... (read in full...)

Is it healthy/normal for a man to have so many female friends?

Q.   Is it weird for a guy to have a lot of friends that are girls, and whose closest friends are girls? Is there ever a time when this is perfectly healthy and NOT a red flag?? The last two guys I've dated have had mostly female friends. At the...

A.   20 December 2010: Having opposite-gender friends is fine, but good people curtail their behavior when in a relationship to improve the other person's comfort. So, no more drinking alone with a chick or having sleepovers, for instance. Generally, most of the guys... (read in full...)

My comatose husband may never wake up. Should I try and raise his baby alone or abort it?

Q.   Hi, everybody i'm new here so here goes... about 2 months ago my husband and i got in a near fatal car accident. i am ok, just came out with a broken arm, but my husband suffered a serious concussion and he has been in a coma ever since. i'm so ...

A.   20 December 2010: This is as much a moral judgement as a practical one. Much as I'd like to, I can't make the moral decision for you. I can point out that you're obviously under duress, which is the worst time to make long-term decisions (but, often, the only time ... (read in full...)

Where did my beautiful loving wife go?

Q.   My wife and I have 3 boys and have been married for 8 years. This year just after our anniversary my wife began an affair. She had become increasingly distant, and I finally asked her what was going on after 6 weeks without intimacy. She flatly told ...

A.   19 December 2010: People change, and consciously choose, guilt-free, not to honor their vows or commitments. Harsh reality at work. Men and women do it for different reasons - and your situation is a classic example of the more common female one. She "doesn't have ... (read in full...)

Can remaining single have a negative impact on a person?

Q.   If a person remains single, does anyone think it can a negative impact on said person mentally? Are there positive consequences to be had? Perhaps a deeper sense of self, or greater self sufficiency? What do you think? I am not talking about jumping ...

A.   19 December 2010: Involuntary single-ness/celibacy can make a person bitter and angry (not without justification) to the opposite sex. Voluntary single-ness doesn't have any negative side effects that I'm aware of. You have more time and freedom, can live on less ... (read in full...)

I just want a guy to respect me!

Q.   Dear Cupid, I am 18 years old i just got out of a 2 year relationship 4 months ago with a guy, im gunna call bob in this story haha but im redeemed and would like to start dating again. I just dont know where to look for a guy who repects me, trea...

A.   19 December 2010: If you're going to change the perception guys have of you, you'll have to really get into their heads, understand where they're coming from, and adjust your attitude to match. Importantly, if you don't want to be judged, don't judge anyone else. ... (read in full...)

Are there any honest men out there?

Q.   I'm 23 and have my own car and job. I'm an honest person who actually wants a relationship. Yet I've been burned twice this year by two players. I'm so sick and tired of being used. One guy cheated on me and dumped me by text message. The other guy ...

A.   19 December 2010: What criteria are you using to select these guys? Is it just any guy that asks you out? Are you looking for fun and excitement? Often, when I hear women say they want a nice guy, what they mean is "I want one of these exciting player-types to be ... (read in full...)

Diamonds are a girl's best friend???

Q.   I love my boyfriend very much and he loves me, we have an amazing connection and we are best friends. He even says that I am his perfect match and he truly wants to marry me in a few years. He had one very serious relationship before me (they lived ...

A.   19 December 2010: Perhaps, like me, he has learned that giving gifts too often or too freely is a good way to cheapen the relationship and turn a good girl into a mercenary. Is he giving you the gift of fun, good memories, loyalty, and emotional involvem... (read in full...)

Why text? Can't guys communicate bad news better than that?

Q.   I know there is this general perception that guys don't like talking on the phone (or generally in fact), but why do so many of them think texting as the sole method of communication is acceptable? I'd like a relationship with a man who wants to ...

A.   19 December 2010: Not sure how you would go about seeing if this is true for the guys you're seeing, but a lot of guys will act in ways they don't want to because they've found it's more effective. For instance, I hate text messages, and would prefer to call for ... (read in full...)

Should I ring him when he tells me to, or do I play hard to get and ring him another day?

Q.   Do you think it's better to ring a guy when he tells you to, or is it better to play hard to get and ring another day ?. This guy i like wants me to ring him tonight, but we are only going to be casual with each other, not in a proper relationship, ...

A.   19 December 2010: The points you lose for seeming "eager" will be far outweighed by the points you win for not flaking on him. You have to give him hope of success before "hard to get" can do any good for you, otherwise he will just think you're not interested at ... (read in full...)

Why if girls/women are around each other do they get their periods at the same time?

Q.   After going through a lot of girls only parties (because I live with my mom and sister .) I've noticed one thing...Why do all girls get there periods at the same time! Its so weird and dont get me started with their mood swings mood swings. Why is ...

A.   18 December 2010: It's not a phenomenon that's been really, conclusively explained. Some researchers doubt it exists (obviously they never lived in the dorms while getting their degrees). The most convincing theory I've seen is competition. Women are most likely ... (read in full...)

I'm feeling empty even though all should be well. How can I improve things for the better?

Q.   I have been happily married for 6 years and very proud to Have a pretty wife and a father of two lovely kids. Just when I should felt like I have everything in the world I have been feeling somewhat empty lately. I miss the time when I actu...

A.   17 December 2010: You have a pretty wife. Find a place to drop off the kids occasionally and re-enact the early days of your dating life. For example, have her go to a bar, and pretend you don't know her and have to seduce her from nothing. Or park the car some... (read in full...)

How can I change my taste in men so I stop getting hurt?

Q.   i have been in one bad relationship after another, i can't seem to break the cycle! i don't know if there is something wrong with me that i'm attracted to these same type of men but they are all alike. how can i turn my tastes to a different sort so ...

A.   17 December 2010: Ouch. That new information is tough. I'm not going to lie, having five kids and living in a small town, on the cusp of 30, is a pretty substantial handicap in the dating game. The best I can do for you is encourage you to keep trying. It may b... (read in full...)

I hate being normal!

Q.   I hate being normal. I've noticed that no matter how many times people say that looks don't matter, hey, THEY DO! I've noticed how my male friends treat girls differently based on looks more than personality. I'm not the most attractive girl, I'm ...

A.   17 December 2010: Let's be upfront: you're right, looks matter. More attractive people get a lot of breaks in life. But life's not fair that way, only way to play is with the hand we're dealt. We'll take your assessment of your looks to be accurate. For the sake... (read in full...)

What are your top 5 "Must haves" and "Can't stands"

Q.   Poll (just for fun). For women and men, for you, what are the top 5 "MUST HAVES" and the top 5 "CAN'T STANDS" when evaluating members of the opposite sex as a potential lifelong partner? I guess mine would be Must Haves: friendly dispos...

A.   17 December 2010: Must have: similar screwed-up sense of humor to mine, cute face, reasonable capacity for intelligent conversation, good Christian values, love of dancing. Can't stand: taking privilege for granted (whether from rich daddy or good looks), slutty p... (read in full...)

What do you do when you are feeling down about yourself?

Q.   I have been feeling unconfident. I would like to know what you do when you are feeling down about yourself? I try looking at myself in the mirror; I feel good for a second then the insecurities comes back. I want to start feeling confident but don't ...

A.   17 December 2010: Nothing wrong with a little make-pretend to feel better about yourself. No different from playing a video game where you're the hero. I get busy with my hands. I'll cook something, write something, build a bookshelf, offer to help the old lady... (read in full...)

When I bring up marriage, he says "its not happening right now!"

Q.   We have been dating 4 and a half years. We have a 1 and a half year old child. And just recently bought our first house together. When ever I bring up marriage he tells me its not happening right now. What do i do? Do I keep in this relationship? I ...

A.   16 December 2010: You live with him, have a child with him, you're having sex with him, and have been committed to him for a while. It's practically like you're married already - it's even possible you're already common-law spouses, depending on what state you're ... (read in full...)

I'm scared that I'm going insane staying with him! WHY am I still with him?

Q.   Why the hell am i still in love with this guy 1. who never wants to marry me since im older to him 2. who breaks up with me whenver he feels that i am pressureing him for commitment and gets back after few days as if nothing hpnd 3. Never c...

A.   15 December 2010: You love him because he's clearly a master of drama. Women love drama - in many cases (not all, but many), women would rather go from happy to sad to angry and back again, than just be happy all the time. This fact alone is what makes nice guys ... (read in full...)

Am I doomed to be the girl who passes up nice guys?

Q.   Dear Cupid. I suck. There's something wrong with me! I'm in an "un-labeled" exclusive relationship with a man whose good to me but has traces of Mr Hyde..I dunno. We'll call him Angelo. But this is the bad part, I've skipped over two...three..four ...

A.   15 December 2010: You're not "doomed" to anything. You control your life, unless you pass that control on to a guy or to your hormones. The posters below are correct, most "nice guys" are, well, boring. Boring is pretty much the opposite of attracti... (read in full...)

Why am I the bad guy here?

Q.   So I am told things about a guy I was seeing until a week ago..that he beat his ex wife (my friend) and put her in the hospital...so i call him to tell him what I was called and told..and he gets pissed at me..I wasn't spreading the rumor...i wanted ...

A.   14 December 2010: Sorry it took so long to get back to this; I've been away a few days. Three steps to dealing with how mad he is. You may have already done 1 and 2, but here they are: 1) Understand what a serious accusation abuse is, especially unfou... (read in full...)

Men, would you date a girl with a tattoo?

Q.   Not a relationship question and i'm quite sure its probably been asked before but was just wondering what guys think of girls with tattoos, not the big sleeves and manish tattoos just dainty ones and ones that have meaning to the individual? Would ...

A.   14 December 2010: Every girl I've ever known with a tattoo, even "dainty" or "individualistic" ones, had either issues or an unsavory past. Easy marks for players, too. For the record, I think the same of guys with tattoos as well. Not saying having those ta... (read in full...)

Thoughts on having sex on the first date?

Q.   is it ok to have sex on the first date/night you meet someone?? recently i haven't had a lot of sex, its been almost 6 months, and although i thoroughly enjoy it, i feel the need to get out there and have a few one night stands.. ive been chatt...

A.   14 December 2010: Depends on what you're looking for. If it's hookups, that's your business, but it doesn't sound like that's the case. Take it from a guy, 99% of the time if you put out on the first date, you have eliminated yourself from the "potential relation... (read in full...)

How can I change my taste in men so I stop getting hurt?

Q.   i have been in one bad relationship after another, i can't seem to break the cycle! i don't know if there is something wrong with me that i'm attracted to these same type of men but they are all alike. how can i turn my tastes to a different sort so ...

A.   14 December 2010: There's nothing wrong with you. Most girls are attracted to the wrong type of guy their whole lives; the only difference is between the ones who learn early and the ones who learn late. Understand the difference between guys who are attracti... (read in full...)

Problems with my boyfriend and how I feel about his family, help me!

Q.   Hi all, My boyfriend is a very high achiever from a very high achieving family. I am a fairly high acheiver from a very dysfunctional family. There are also cultural and religious barriers that we are trying to overcome in order for our realtio...

A.   14 December 2010: In response to the second question, saying "I love you" is giong to be awkward until you've done it for a while. Just give it time. In response to the first, one day you very well could have a loving, supportive family, you'll just be the moth... (read in full...)

Does he love that I'm sexy, or does he actually love me?

Q.   my boyfriend has told me he loves me a couple of times. but last time he told me he said i love sexy you so so much your my everything does that mean he loves that im sexy or that he loves me?...

A.   14 December 2010: If you've been dating him more than three months, and/or waited more than three dates to sleep with him, he loves you and thinks you're gorgeous. The two are not mutually exclusive - in fact, they reinforce each other. Some guys will lie about lo... (read in full...)

Why do men get defensive when asked to wear condoms?

Q.   hi dear aunts and uncles. why men don't like wearing condoms and get defensive when you ask for it? they always throw the 'you don't trust me' line. that doesn't work with me be cause i believe that no glove no love is the best thing to do. but ...

A.   9 December 2010: Honestly? Condoms suck. Not that I've ever met a woman who preferred them over the real thing, but you're right, safety first. They try because they want to raw-dog, and figure that asking won't hurt their chances of getting laid anyway. ... (read in full...)

How do I find a girl with my same interests at my college?

Q.   Its been about a month since my bad break up with my girl friend of two years whom I thought was "the one." She started dating another guy almost immediately after we ended things which seriously hurt and broke my self esteem a bit. But now I...

A.   9 December 2010: If you're in the dorms, the common room of the dorm hall is usually a great place to meet girls and friends. Remember to make platonic female friends, and keep them all four years - partly because they will have a never-ending supply of cute female ... (read in full...)

13 year old son sexting. What should his punishment be?

Q.   Just caught my 13 year old sexting with a girl in his class. They sent each other pictures of each other and everything. Not sure what his punishment should be. His phone was taken indefinitely. Not sure what else I should do. What do u all think?...

A.   9 December 2010: You can show him these links. http://abcnews.go.com/Nightline/phillip-alpert-sexting-teen-child-porn/story?id=10252790 http://www.gadgetell.com/tech/comment/sexting-can-label-your-teen-a-sex-offender/ http://www.aclu-wa.or... (read in full...)

How do I deal with favouritism at work?

Q.   I love my job with all of my heart. I have heard rumors of favoritism and people not being allowed to grow and get promotions, etc. I have seen first hand that people are not treated equally at my job. The favoritism occurs at the highest levels, ...

A.   8 December 2010: Part of the real world is networking. "Who you know" is the single most important factor for success in the professional world, at least from what I've seen. Way it is. Still, you would benefit from focussing on your own success rather than wor... (read in full...)

I'm a quiet and shy person but what do their comments mean?

Q.   I was wondering if anyone could help me figure out what each of these comments mean. I feel offended and ebarassed when people point out my shyness, especially by the way they mention it. I've had people saying things such as " what's wrong with you ...

A.   8 December 2010: Confidence can only really be gained by experience - but you can fake it until it feels real. Learn to accept that some interactions will be awkward, or embarassing, or simply lead nowhere. You gain experience whether you do well or not. Bring a ... (read in full...)

Why am I the bad guy here?

Q.   So I am told things about a guy I was seeing until a week ago..that he beat his ex wife (my friend) and put her in the hospital...so i call him to tell him what I was called and told..and he gets pissed at me..I wasn't spreading the rumor...i wanted ...

A.   8 December 2010: Are you sure he did it? False accusations of abuse are depressingly common in bad divorces (but then, abuse is also depressingly common). Find out if there's some way you can check with either the hospital or the family court about the records.... (read in full...)

Is this a move that alot of women put on men?

Q.   So we just started to date, we're entering our 4th month now and at first we agreed to have a casual relationship, but now she is starting to fall for me (so she says) and is asking me to become exclusive with her.. I'm noticing that she's been very ...

A.   7 December 2010: Alright, I think I can interpret what's going on in her head, but one point first. You're probably going to get a few answers shaming you about how you feel about her. Don't worry too much about it. You are entitled to your feelings. Arguing ... (read in full...)

I'm not happy about my girlfriend's pregnancy, I don't want to let my dreams and goals go down the drain!

Q.   I'm 23 and my girlfriend is 20. We found out a couple weeks ago that she is pregnant, and she's ecstatic, I am more reserved. When we found out our reactions were very different, she was happy, I was upset. To cut a long story short she has decided ...

A.   7 December 2010:  1) You are not selfish for having your own wants and dreams. Acting and directing are tough fields, but not impossible to get into with persistence. Fortunately, as a guy, you will have an easier time getting auditions and roles as you age if y... (read in full...)

No, means no!

Q.   I met this guy when I was walking home from university the other night, we talked and I ended up getting his number. Last night he came over to my place to "hang out" and he all but told me he loved me! We did kiss, and he seemed to want more as ...

A.   6 December 2010: Agreed, this guy sounds like a boor. Good word for it. I sincerely doubt he would rape her, since he didn't this time, but it would still be wise in the future to have a few dates outside of the house before inviting a guy over. With that sai... (read in full...)

Do some guys act this way even though they love their girlfriends?

Q.   I am receiving mixed signals from my current bf. And I really don't know, does he love me or not? First thing that I don't like, he rarely calls or msgs me on my mobile phone. Except only if he is coming to see me (he lives 2 hours away), tha...

A.   6 December 2010: I'll just address each point in order. 1) Most guys communicate only because they have something to say - like, "I want this," or "I am now ready to do seomthing for you, tell me what you want." Stories have to be exciting or unusual, rather t... (read in full...)

He tries to cover up his erection!

Q.   hi, every time me and my boyfriend hug he gets a erection but when he does he moves away from me.like we're on the sofa cuddling and he just moves away from me i don't want him to keep moving away from me evey time why'd he do tha? what should i say ...

A.   6 December 2010: He gets the erection because he's young, full of hormones, and attracted to you. He turns away because, honestly, erections are kind of embarassing in non-sexual situations. Plus, sometimes it gets uncomfortable, depending on the pants he's wea... (read in full...)

Men, what are your favourite sex positions and why?

Q.   Men, what are your favorite sex positions and why?...

A.   6 December 2010: Sitting or standing, back straight up, her facing away from me, but looking back over her shoulder so I can alternate between kissing her face and neck. I get to hold her close and tight, with the freedom to do basically anything with my hands ... (read in full...)

Obsessed by my girlfriend's sexual past........and I like it! Am I weird?

Q.   Me and my girlfriend have been together for 4 years. Our sex life started well, but then dwindled to once a month at most. I have always liked the thought of her being with someone while I watched, and we used that to turn ourselves on for a while. ...

A.   6 December 2010: This is a cuckold fetish. Basically, it's triggering the instinct to screw a woman immediately after she's been screwed, during your last chance to impregnate her (obviously a tremendous oversimplification, but you can research the more in-depth ... (read in full...)

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