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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...

< Prev56789101112131415Next > [38 pages, 1485 answers]

What do guys prefer?

Q.   Do guys who normally prefer the "bimbo" look on girls (meaning bleached or dyed long hair, tanned skin, skinny, revealing clothing,) also like "average" girls or not so much? ...

A.   17 June 2011: Depends on what the guy is looking for. A one-night-stand? A fling? LTR? Think of it this way - if a guy just wants to get laid, no strings attached, is he going to talk to the girl in the stripper pumps with the plunging neckline, or to the s... (read in full...)

Is wanting to cuddle a sign of neediness?

Q.   Well, I'm dating again after a long sabbatical, and I've found a girl I really like. However, I'm finding it hard to be affectionate. I'm worried that it may be too much to soon. After our fourth date she came over the next night to hang out. We sat ...

A.   17 June 2011: It's fine to want cuddling, although you're right to want to avoid the image of neediness. I think you're overdoing it a bit here, though. Just take up the dominant position in the cuddle. To use the couch as an example, sit straight up as if yo... (read in full...)

Why doesn't my boyfriend feel comfortable with me wantimg a threesome knowing I'm bisexual?

Q.   i have a boyfriend who i love and he loves me to and i wouldnt try to change him in anyway..! i like guys and girls and i have dealt with females my whole life but slowed down at 19... (im 23) but a few months ago i told my bf i like girls and h...

A.   17 June 2011: Not every guy is a raging horndog. If he actually likes you for you, there's a good chance he'd be uncomfortable with the thought of you having sex with anyone besides himself - and that includes other girls in threesomes. I'd be willing to bet ... (read in full...)

Is it worth trying to confess to him?

Q.   I expected this guy to tell me he liked me but he didn't and now high school is officially over for us both. This is the silly part. We have NEVER had a conversation with each other. We are also possibly complete opposites. He's very popular and ...

A.   17 June 2011: Confessing to a crush all at once is a certain way to destroy your shot at it, despite what you see in movies. And as much as girls want guys to always make the first move, the downside of that approach is that you will miss opportunities as the ... (read in full...)

Why do women keep walking all over me? And what should I do about my ex?

Q.   [Mod Note: 2 posts have been combined into 1] my gf has been blowing hot and cold never letting go of her past. (i was her rebound) which over the time we were together i came to realize. She has lied to me about contact with her ex several times i ...

A.   17 June 2011: The minute you let someone walk all over you, they lose all respect for you. Respect is vital in any relationship. Why would this girl, or any other, bother to treat you well if you take them back after they lie, or let them see their ex while ... (read in full...)

Why would a musician want to be with a girl who is outspoken and not crazy over his band?!

Q.   I have been seeing this guy for about two weeks now who is the lead singer in a band and I don’t understand why he is still interested in me when I know I am blunt and direct at times, nor do I take much interest in his band. They’re really good, ...

A.   16 June 2011: You like him, and are attracted to him, and are honest with him. So that's one point in your favor. But you're differentiating yourself from other girls by liking his music without liking him for his music. Different is good. Addit... (read in full...)

I did not get pregnant after my partner ejaculated within me. Does this mean I won't be able to have kids?

Q.   Helpppppppp!!!!!... I had unprotected sex with my partner and he ejaculated inside of me in June 5th, i got my period i believe on june 11th. may i not be able to have kids?...

A.   15 June 2011: While that's certainly possible, it's far, far more likely that you just got lucky. While you risk getting pregnant anytime you have sex, the time you list would not be during the most fertile part of your cycle. Don't take this as an excuse t... (read in full...)

How do you say no when a guy asks you out?

Q.   When a guy asks you out, and you don't like him that way, how do you say no? Because there is this guy who likes me (I've had over twelve people, a few of which i don't really know, but they knew my name, tell me. He stares at me in class. He always ...

A.   11 June 2011: Maybe he overreacted because he's got issues, or maybe he overreacted because he got emotionally invested in her. If the latter, she may have had a hand in it by not shooting him down quickly and clearly (do you know if this was the first time she ... (read in full...)

Girlfriend/Boyfriend Loosing/lost Interest

Q.   The Views posed in this article are controversial. Read with discression. Women and men are guilty of pushing thier views on to the other person and putting restrictions on the things they would normally do when single. The biggest one is. ...

A.   10 June 2011: Glad you liked all that. I understand the rebellious attitude completely, too. Haven't quite grown out of it, myself, and I kind of hope I never do. If I had to guess, I think it's not just a rebellious attitude at work, but an issue with trust. ... (read in full...)

Should I confess to my husband?

Q.   I have been married for 3 yrs and have a little boy. I have not been happy in my marriage for a few years now, just feel as though I'm not appreciated and feel tied to the kitchen sink. Recently I have been confiding in a male friend at work and ...

A.   10 June 2011: He deserves to know what he's getting into if you're going to get back with him. If you feel tied to the kitchen, would I be correct in assuming he's the primary breadwinner? If so, that only increases his right to know who he's providing for. ... (read in full...)

Should she give the engagement ring back?

Q.   After 2 years with a wonderful girl I proposed... She said yes! We were planning on moving in together and then got into an argument about money. She says I had a look in my eye like I was going to hit her.... I wouldn't touch a hair on her head! ...

A.   10 June 2011: Engagement rings are actually a fairly young tradition, less than a century old (unless you count royalty, or the grass rings woven around the wrists and ankles of brides-to-be in Celtic tradition). But that aside, "traditionally," the ring was ... (read in full...)

Questions from health class

Q.   so in health class we are having the sex education talk and i'm not planning on having sex anytime soon hhahaa no worries specially cause i'm 15 but anyways my teacher said that sex should not hurt unless the guy is going too hard.. and i mean i ...

A.   10 June 2011: Good on you for waiting for sex. It's rewarding to wait for the right person and circumstances, I hope it all works out for you when you start. There are a lot of positions that can increase a girl's pleasure during sex - and that's leaving ... (read in full...)

I still do love her. And I do want her back. So how can I get her to come back to me?

Q.   hey my ex broke up with me 2 months ago and we were together for 1 year and a half. Tomorrow is the last day of school. but she completely changed. now all she does is hang around the people I'm jealous of, she sings a lot now and she only sang in ...

A.   10 June 2011: OK, this is hurting because you aren't allowing the breakup to finish up cleanly. She's not coming back, and after how she's acted, I'm not sure she deserves to. Maybe you love her, but that love is misdirected. There are worthier girls out ... (read in full...)

My first relationship was controlling -- how to get past it?

Q.   Hi.. i know my situation is complicated but bare with me please.Ok im 16 and 6 months back i was seeing a guy for 1 yr and 4 months we meet through a prank call ironic i know but he knew my best friend at the time he was new.Problem was my best ...

A.   10 June 2011: I know this hurts. Life's rough sometimes. Up until the cheating part, I'd have said that it was just an extreme case of not knowing how to date someone. Everyone is a terrible boyfriend/girlfriend the first time around, objectively speaking... (read in full...)

Girlfriend/Boyfriend Loosing/lost Interest

Q.   The Views posed in this article are controversial. Read with discression. Women and men are guilty of pushing thier views on to the other person and putting restrictions on the things they would normally do when single. The biggest one is. ...

A.   10 June 2011: Anyway, that was fun. Thanks for putting up the article.... (read in full...)

Girlfriend/Boyfriend Loosing/lost Interest

Q.   The Views posed in this article are controversial. Read with discression. Women and men are guilty of pushing thier views on to the other person and putting restrictions on the things they would normally do when single. The biggest one is. ...

A.   10 June 2011: I think you're trolling, but I love feeding trolls. This is gonna be fun. With that in mind... Not sure where to begin here, so I'll pick at random. "Well this can damage things because your telling someone they cant do something..." ... (read in full...)

Is it wrong to break up with a friend because you find their way of life offensive?

Q.   It seems like to be a good friend means to be supportive. And we are all told we should not be judgemental. But what happens if a friend has habits you find offensive and which go against your value system? Are you a terrible person if you want to ...

A.   8 June 2011: Nothing wrong with being judgmental. Anyone who says otherwise is judging you for you opinions, the dirty hypocrites. Besides, it not as if you're advocating passing a law against her kind of behavior, you're just choosing to distance yourself ... (read in full...)

When is it the correct time to ask a girl out before they say "we are just friends"?

Q.   i have fallen into this situation many times. i always meet new girls and well i get to know them but then when i ask them out they say that im just a friend. is it because i know them to much? when is the correct time before i get in the "friend ...

A.   8 June 2011: As soon as possible. At the very least, make it clear that you are interested the first time you meet a girl by getting her number, then calling within two or three days to meet up. The exception is if you know for a fact you'll keep seeing a... (read in full...)

Is he after 9 years growing apart? We love each other but what is going on?

Q.   I have a problem, my bf and I have been together for 8 years going on 9 years. I'm currently going to school and he is to. we are both finishing school in a couple of months. Anyways, there was a time when he and I where very close. He would hug me, ...

A.   8 June 2011: You didn't say anything in the post about flirting or playful behavior with him. Are you taking the time to tease and flirt when you talk? Do you stop randomly to rub his shoulders or grab his ass? Do you wear heels and a short skirt around the ... (read in full...)

He's controlling and has anger issues. So why do I want him back?

Q.   I dumped my ex twice within a three month period. He was controlling and acted more as my father than my boyfriend. He would ask me what I was doing when I was too busy to text him back quick enough, or when I occasionally didn't initiate contact. ...

A.   7 June 2011: Most women are into dominant, powerful guys. Your case is just a bit stronger than the average, and you are attracted to the fact that you can't control him and he's willing to assert himself so brazenly. The only real way to fix it is to cut a... (read in full...)

What is it really like to be a mistress?

Q.   What is it really like to be a mistress? I have been propositioned by a married man I've known for 2 years. He is 24 years older than me and he really turns me on. Obviously I know this is wrong but it all just sounds amazing. Plus he's had a rocky ...

A.   7 June 2011: How much you'll enjoy it depends on your personal capacity for guilt. If you can stomach the idea of aiding and abetting a man in betraying someone he swore loyalty to, you'll enjoy it up until the moment you realize that only 3% of mistresses ever ... (read in full...)

I just get the feeling that I give give give, and get nothing in return.

Q.   Hello. Recently i have been unhappy. I keep thinking maybe i am just being stupid, melodramatic, and childish. But i cannot shake the feeling that i don't mean anything to anyone. I am an only child, so loneliness is always a factor but its n...

A.   7 June 2011: It sounds like you're going through a real low point from the breakup. We've all been there in varying degrees - you're not alone. Take comfort in knowing that many people have had similarly bad times, and if they can survive and be happy again, ... (read in full...)

I thought we had a connection, what went wrong?

Q.   i met this guy online a couple months ago. we messaged back and forth a few times, and talked on the phone a few times. ive done the majority of the initiating, and it takes him awhile to return a message, but he always sounds happy to hear my voice ...

A.   7 June 2011: I see two main possibilities here. 1) He's a nice guy, who's probably been burned in the past, not enough to screw him up, but enough that he takes things slow and steady. In this case, he does indeed notice the googly eyes (love that term) an... (read in full...)

My ex has moved on with a new guy, who's very different from her ideal guy. What do I do now?

Q.   Hello, I'd just like to say thank you very much in advance for taking your time to read this and reply.. About a month ago my ex girlfriend broke up with me after 2.5 years. I met her when we were both 16, yet I was one year older than her school-...

A.   7 June 2011: "I knew I'd miss her and vice versa... We spoke every day" This is where the problem started. It's not bad to keep in touch with an ex, though I don't think it's a great idea most of the time, but in this case you allowed yourself to believe ... (read in full...)

What's the deal with slapping during sex?

Q.   Hi I am curious to know why some men like to slap women around the face when having sex,do they have some sort of problem or are they violent types and like to dominate women do they care about the person they are hitting or is it just some sex...

A.   7 June 2011: Unless you're talking real, bruising slaps, it's not a violent thing. It's just part of cutting loose for some people, part of the more animalistic side of our nature. Generally speaking, in bed, men like being dominant and women like being ... (read in full...)

Did I miss the relationship train?

Q.   It would be wonderful to get some insight regarding how to get over something. I would like to share my life with someone, but I have been feeling a little down. I have always had guys as close friends and never got into a serious relation...

A.   7 June 2011: You're going to have to lower your standards in some area or another. The average and median age of marriage is lower in Mexico than in America. Even here, Latinos get married earlier than white folks. What that means is that, as you've noticed, ... (read in full...)

Why shouldn't a girl ask a guy out?

Q.   I"m gonna make this as short as possible: I like this guy at my college who is also a close friend. I have only told 2 people about this because 1. I don't want the whole school to know and 2. because no one actually thinks I'm being serious!! ...

A.   2 June 2011: There's no reason not to ask him out. No one would look down on you, and he may very well respond positively to it. At the very least, it demonstrates your own confidence, to yourself and others. That said, I know most girls really, really p... (read in full...)

What exactly is so enticing to a guy about releasing onto a girl's stomach/chest?

Q.   dear cupid, soo, this might seem like a weird question, buuut it's just something that's been on my mind lately. soo, hopefully, somebody on here will be able to answer it. hahaa...anyways...here goes. my boyfriend and i were just about as close t...

A.   2 June 2011: It's mental/emotional. It's just awesome to have a girl so into you that she's going to let you get off all over her. Plus, you can see her whole body as you do it, so there's a strong visual element, too. If you want to make it even better f... (read in full...)

Do you think its ok to have a couple's profile on Facebook and for me and my BF to share it together?

Q.   My boyfriend made the suggestion last night that we delete both of our facebook profiles and create a new one that is a couples profile and share it together that way the people that add us or that are real true friends will not have a problem ...

A.   2 June 2011: This sounds like the twenty-first century version of getting your names tattooed on each other - instant breakup material. I'd say don't do it.... (read in full...)

Awkward Virgin Moment

Q.   So, I'm having a little problem with something that's been bothering me for a while now. I am a virgin, 18, that was dating my first and only girl last year. We got along great and connected prefectly! Then one night, her parents went out of town ...

A.   1 June 2011: You can't count on the girl to escalate or take initiative unless you're in a rock band. Don't sweat it, though, those awkward first steps are part of the whole experience. My first time sharing a bed with a girl was the same way; I had no idea ... (read in full...)

What to do when a girl keeps flaking?

Q.   So,there was this girl I used to  date (note: first and only girl ive ever dated past a first date)... I liked her a lot.  If i had a list of everything I wanted in a girl, it would have been her. We dated for like a month and a half...but she was ...

A.   1 June 2011: If she flakes consistently, it means she doesn't like you, in either sense of the word, she just likes the attention you give her. It means she's selfish and doesn't want a relationship or friendship, she just wants the benefits of one without the ... (read in full...)

Why do guys keep hurting me like this?

Q.   Why does this keeps happening to me? what is wrong with me? Am all cried out! I've had 4 boyfriends who I felt really strongly about. I did everything a good girl would do. I wasn't easy, I stick to the rules and made them all wait a reasonabl...

A.   1 June 2011: I'll second everything YouWish said. It's important to remember that if you pick the wrong guy, nothing you do can change what they'll do. There is no way to be an awesome enough girlfriend for a cheater to decide not to cheat, or for a jerk not... (read in full...)

My cousin is going to blackmail me unless I do sexual things with her, and she's only 13!

Q.   help cupids! im in a really BAD situation. basically, my cousin is blackmailing me for not doing sexual things with her. let me explain. my cousin admitted to me she loves me (though previously, i think she just adored me and now i know its jus...

A.   1 June 2011: First off, stall her while you set up a defense. One false accusation could destroy you, and she sounds like she's got serious enough issues to do that. "If I can't have you, no one can!" Speak to your parents first about this. Not to hers. H... (read in full...)

I was falsely accused of a crime, and my girl hasn't treated me the same since it happened!

Q.   We been togther for just over 4 years. For first two years we had sex almost everyday where ever we could, and when we both had the same days off work we spent the entire time in bed having sex. She held my hand everywhere we went, wasnt bothered ...

A.   1 June 2011: What's the point of a relationship without loyalty? She walked the moment you received some wild accusation, and even now is frigid. Given her new frigidity, the way she's avoiding you, and the way she's only warm when there's no way she can see ... (read in full...)

Kissed another....Should I tell my hubby???

Q.   I've been married 2 years, together for 9. Last year I kissed another man on 3 separate occassions. I felt disgusted about what I did and put an immediate stop to it. I never told my husband. I was able to live with it up til now. We just bought a ...

A.   1 June 2011: If you'd done it just once, that'd be one thing. Anybody can lose control for a second or two, and most reasonable people would forgive that. I'd still advise telling him, but not too strongly, and if he were to come on this site saying "My wife ... (read in full...)

His comment about my weight were rude and uncalled for, what should I say to him?

Q.   I've been dating my bf long distance for almost 15mths now. Since I've met him, I've gained about 10-15lbs. Two nights ago, we were texting and I mentioned that I had started a new workout the day before and my body was achy because it was s...

A.   1 June 2011: Let it go. It was a joke; one which was based in reality, but still a nicer way of saying it than "Lose the weight." If you get upset about this, not only will you be less happy, but you'll look crazy and hypersensitive in front of him. Better t... (read in full...)

Why has she stopped being interested since I told her that I like her?

Q.   So I like this girl, and she liked me for a time, we were talking, texting, meeting up. But all of a sudden since I told her I liked her she doesnt seem interested and is always too busy to meet up. I feel I've lost my chance with her but is there ...

A.   1 June 2011: You took the mystery away. Girls want relationships to "just happen" as if it were fated, rather than a conscious and informed decision by both parties. It's only after the relationship has begun that they start wanting to spell things out. ... (read in full...)

How do you respond when a guy compliments you?

Q.   There is a guy i've known for about 2 years now, i'd say we were quite good friends, but in the last year he keeps talking to me online and telling me that im beautiful and gorgeous, which is really nice and I do like compliments, he will also write ...

A.   1 June 2011: Compliments in general are easy: thank the guy, and offer a compliment in return if you have one. I think this case is special, though. If he's writing poems for you, he really wants to date you, and you need to avoid leading him on. A lot of g... (read in full...)

8 years, 1 child, another on the way..how do I get him to marry me?

Q.   My fiance and I are both 28 and have been together for eight years. We have a three year old son and I'm currently 8.5 months pregnant with another boy; we even have three fur babies (a dog and two cats)! We've talked about it several times when we ...

A.   1 June 2011: Come up with something in his life that will improve, and stay improved, if he marries you. What does he stand to gain? If he's happy with your family as it is, why would he want to change it? If you phrase it in terms of your "expirat... (read in full...)

Is there any man out there who is satisfied with just one good woman?

Q.   Can someone please tell me what is wrong with men? They say they love you, it feels right together, you have so much in common..... you are both having fun and things are great......Then why oh why, do they seem to think they need more than 1 ...

A.   1 June 2011: It's not most men, not by a fair margin. There's selection bias. Cheating men are more heavily represented in the dating scene. Think of it this way. Say you have three guys who are faithful to their girlfriends, and one guy who is cheating... (read in full...)

What are the defining qualities that you look for in a man, from initial attraction to wanting to develop a relationship with someone?

Q.   Question to the women out there on dear cupid... What are the defining qualities that you look for in a man, from initial attraction to wanting to develop a relationship with someone? I only ask this for a little advice as I struggle quit...

A.   31 May 2011: This is a good question to ask the women in your own life - be they friends, sisters, or your cousin's roommate's ex girlfriend. Compare the answers they give to the guys they have actually dated. You'll notice a huge discrepency between what ... (read in full...)

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