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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...

< Prev1819202122232425262728Next > [38 pages, 1485 answers]

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...)

Everyone needs to be aware of bullying and put a stop to it

Q.   This is a tip for people who are being bullied. PLEASE TELL SOMEONE IF YOU ARE A VICTIM OF BULLYING NO MATTER WHAT TYPE IT IS OR HOW SMALL. It is devastating to hear on the news about a young person committing suicide over bullying. I do not ...

A.   5 December 2010: One would imagine the martial arts experience only makes it harder for her. These days, zero tolerance policies make self-defense a quick ticket out of school. Having the power to defend oneself and no way to use it must suck. She has my ... (read in full...)

Does pre cum have sperm in it?

Q.   Okay so no criticism please. I have a couple of questions here. First, I'm on my period so I had a tampon in, but me and my boyfriend sort of had anal, but it was mostly just him rubbing his penis on my butt, but I could feel that there was precum. ...

A.   5 December 2010: Yes, it's possible for some sperm to be in precum. With that said, the situation you describe makes it extremely unlikely that you've gotten pregnant. He didn't go in your vagina, you had a tampon in, you weren't on your fertile phase, you're a... (read in full...)

Spit or swallow?

Q.   When giving a blow job is it better to spit or swollow? My boyfriend of 4 months has recentley asked me to give him a blow job, but im not sure whether to spit or swollow. I've heard it tastes horrible but if i spit, where do i spit? I really dont ...

A.   4 December 2010: Swallowing is definitely way better. Aside from the psychological component, swallowing it as it comes out just feels much nicer. No reasonable guy will consider spitting to be an insult, or even having them finish off outside of your mouth - ... (read in full...)

Guys, what do you like when looking at a gal?

Q.   this is just for abit of fun really lol. I've never had a BF, and honestly aint that interested, but lately I've decided that I'm going to make abit more of an effort with my apperance/clothes etc etc. Then that got me wondering what guys actua...

A.   3 December 2010: Long hair, good waist-to-hip ratio, a pretty face with that kind of makeup that looks like she's not wearing any. Wearing very tight clothes that completely cover the breasts is more alluring to me than cleavage, whatever the size - and for smal... (read in full...)

I really want a boyfriend. How can I get one?

Q.   I desperately want a boyfriend. I know this sounds really desperate but most of my friends and friends of friends have now got boyfriends and I am like the only one not to have a boyfriend can you please help me on this subject how will i get...

A.   3 December 2010: Well, you're going to have to answer a few questions for yourself. Not judging, just helping you strategize. Do you want a boyfriend just to be like your friends, or do you view a boyfriend as a means to your own personal happiness? If the form... (read in full...)

Coping with my fiance's extremely promiscuous past

Q.   I'm falling apart trying to deal with my fiance's questionable past. I've been reading similar posts from other guys on the subject for the past few months, and although they've helped a bit, the extreme nature of my case leads me to create my own ...

A.   3 December 2010: Alright, so she's been with around 250 people, she was not (and definitely still isn't) a believer in monogamy, she's had two kids out of wedlock to bad boys, she's divorced, she had sex with people while dating you (still counts even if you weren't ... (read in full...)

A question for the female aunts...

Q.   I have a vagina question for the ladies. Is it true that during intercourse,if a woman wants she can move her vagina muscle to speed up her man to cum?...

A.   3 December 2010: Not a lady, but I know what you're talking about here. It's called the PC or "Kegel" muscle. Next time you go to the bathroom, stop peeing halfway through. The muscle that lets you do that is the Kegel. You can excercise it same as any other ... (read in full...)

Would you consider his magic number high for his age?

Q.   Is 22 sexual partners for a 27 year old male a lot?...

A.   3 December 2010: MSNBC says the average man sleeps with 20 women in his life (the study does not take "lying your ass off" into account). This figure is deceiving because the median is seven - median would be a better indicator in this case; if you have ten guys, ... (read in full...)

How do you know when you've done the right thing?

Q.   Hi, I've been going out with my girlfriend for almost three years (anniversary next week) and she moved in with me in April. However over recent months we've been drifting apart, or should I say I have. She made it clear that I was the one and ...

A.   2 December 2010: Just want to second Dirtball's advice. He's got it right here.... (read in full...)

Why is it we "hurt the ones we love?"

Q.   Why is it we "hurt the ones we love?" I know it's an old saying but I think there is much truth to it. We hurt the ones we love most. I wish it weren't true or even knew how to change it. It is no secret that I love my wife very much. It's no se...

A.   2 December 2010: Set the tone for your interactions before they begin. If I'm feeling angry on my way home, I stop, take a deep breath, and come up with something positive to do the moment I see her. A five-to-ten second kiss works, and so does a slap on the ass. ... (read in full...)

What should I do if a girl gives me eye contact?

Q.   When the girl I like stares at me I tend to look quickly away because I get nervous. Can someone give me tips on what to do if this happens again. Should I maintain the eye contact?...

A.   2 December 2010: Keep looking. Don't stare wide-eyed or anything, just keep looking, taking in the details of her face, and smile after a few seconds. Raise your eyebrows a bit when you smile or it looks fake. If she smiles back, walk over and say "Hi." Just ... (read in full...)

How can I be more confident and feel more sexy?

Q.   Any tips for confidence? hi I've started dating a guy and we have great sexual chemistry between us. Thing is I've rescently put on a bit of weight and with it lost a bit of confidence. any tips for having more confidence in my sexy self?..he m...

A.   2 December 2010: Start eating healthy and going to the gym. Besides helping you lose the weight, which will always cause self-doubt, both activities actually make you feel happier, more energetic, and more confident. Try getting most o fyour calories for breakfas... (read in full...)

Love Triangle, Mr. Big vs. Aidan. Who Should I Choose?

Q.   I'm in a Love Triangle, which you could compare to Sex and the City's Carrie-Mr.Big-Aidan. And I don't know who to chose. In my case I've been in a relationship with Aidan for a year. He's the sensitive type that would do anything for you.He's down ...

A.   2 December 2010: First, remember that show was written specifically to create appealing drama and garner ratings, not to portray a realistic way of handling relationships. Real life is rarely so forgiving. Anyway, relationships where one party leaves another ... (read in full...)

Will a rebound help me get over a broken heart or will it just postpone the heartbreak?

Q.   Me and my boyfriend of two years just broke up a few days ago. It has been in the works for some time and I have been getting closer to a friend of mine. He wants to have a relationship with me and I think I want to also. He knows I have just ...

A.   2 December 2010: I'd say take the shot, but try not to make it a rebound. Love does not wait for convenient timing, but it's also fragile when mishandled. Try to form a real relationship with this guy, but take it as slowly as you can. It'll be easier to get over ... (read in full...)

Do I really not have adult rights at 18?

Q.   Do I really not have adult rights at eighteen? I went to the ER and they told me they needed my mom's signature. Then my mother told me she made an appointment at the gynecologist because I have irregular periods and told me the doctor will need to ...

A.   2 December 2010: Not to put too fine a point on it, but you're not exactly talking like an adult. Re-read your last three sentences. I understand this is frustrating, but there are two points to consider. 1) Are you on your parents' insurance plan? If so, yes,... (read in full...)

He ran off when I told him I'm pregnant!

Q.   ok im 27 weeks pregant with his baby and i told him. he ran off now he's with someone knew and there 5 years his junior do fellas get with girls that quick or is it cold feet and as soon as he sees the baby he will wake up or is he/all men like ...

A.   2 December 2010: Depends. It sounds like you and he did not deliberately conceive. If you decide together to have a baby, most guys will stick around, and the ones that don't are rightly considered scumbags. If, on the other hand, it just happened by acci... (read in full...)

Girlfriend has a low sex drive

Q.   I'm 27 and I've been with my girlfriend, 26, for almost 3 years. I love her, but there is a big lack of sex; averaging once a month or less ( we sleep together almost every night). In fact we never really had a lot. Every once in a while, we would ...

A.   1 December 2010: Generally, I think low sex drive is a problem that can be fixed, but if you never had that honeymoon period of doing it like rabbits, she probably never will. Unless you believe you can live with this kind of sex life forever, I'd say it's time to ... (read in full...)

What's with this threesome double standard?

Q.   My boyfriend told me he'd like to try a threesome. I told him I'd do it but that I'd also like a threesome but with another guy. He went from totally enthusiastic that I said yes to furious. I told him I didn't want him to do anything with the other ...

A.   1 December 2010: Keep in mind as you read this, I'm not trying to call it fair, or morally justify it, just explain how he's thinking. On those grounds, I'm completely against threesomes in general. I think you'll have a very difficult time finding a guy who does... (read in full...)

Worried about these little black bits!

Q.   I really want to do things with this lad, but you know when a man shaves loads round their mouth? Well, "down there", has gone like that because ive shaved too much! Even when i shave it again you can see little black bits. What do i do?!...

A.   30 November 2010: As a guy, I can tell you that the dark stubble around my face never goes away unless I use a straight razor - which takes way too much time and effort unless I have an interview or a special date planned. You could wax if you want all of it gone,... (read in full...)

He'd rather touch himself than touch me!

Q.   I dont know where to start or if my marriage is too far gone. He has informed me that he would rather masterbate to porn than to touch me. We do not have a very active sex life and he has always stated it was because of his depression. I find out ...

A.   30 November 2010: It sounds like he's given you the two parts of the problem. 1) Depression. Either that's causing the lack of sex drive, or the meds he is taking for it (if any) are causing that. Talk to whoever's prescribing it. Also consider that sex naturall... (read in full...)

Has anyone got any good pickup lines?

Q.   there is a girl who i have a crush on but i dont know what to say to her when i ask her out, any good pickup lines?...

A.   30 November 2010: You can use a pickup line if you make it blatantly obvious that it's a joke, and you're not taking it seriously. A better plan, especially for the scenario you've listed, is to say Hi, ask her about her weekend, make a joke about it, then ask if s... (read in full...)

I eat less than my boyfriend and exercise more, so why am I the one gaining weight?

Q.   I eat less (including less unhealthy stuff) and exercise more than my boyfriend, but I am getting fat and he isn't at all! Why? It's making me insecure!! ...

A.   30 November 2010: His metabolism is probably just faster than yours. When you say you're getting fat, does that mean your body is expanding, or just that the number on the scale is increasing? Remember, the number doesn't matter, how it looks matters. Muscle... (read in full...)

Is he going to marry me? Or not?

Q.   Please help! My boyfriend of one year seems unsure if he wants to marry me. This really hurts me because at this pont am ready to be married to him. He used to be so sure about getting married--but lately he said.. we didnt get along so well that he ...

A.   30 November 2010: Is it more important to you to *get* married, or to *be* married? The former is easy, just find some dupe who won't sit back and think about it. The latter is more difficult. The kind of guy willing to go that route is going to need time to ... (read in full...)

Why is it so bad someone my age has sex?

Q.   Hi, I was thinking today, why is it so bad someone my age has sex? I assure you I haven't but I was talking to my mom and she said as long as you are responsible(using multiple forms of birth control) and had sex with someone you trusted and knew ...

A.   30 November 2010: People your age have a harder time planning long-term. The risk of babies and STD's are more abstract until you've seen a few friends end up with them. Not to mention the emotional aspect of it. Additionally, the earlier someone has sex for the ... (read in full...)

Why do cheaters feel entitled to lie, sneak and hurt others?

Q.   Hi all, when I read through questions and answers I read about people cheating on others (my ex did it to me) It literally tore me apart. But my question is; If you are a cheater, Why do you do this? Why can't you get out of a relationship honestly ...

A.   29 November 2010: OP: Wasn't wrong of you at all to shout it to the world. My point is that it doesn't happen often enough - and the ones doing it are always the ones who learned they were being cheated on, never friends or other associates. Think of any ... (read in full...)

Why do cheaters feel entitled to lie, sneak and hurt others?

Q.   Hi all, when I read through questions and answers I read about people cheating on others (my ex did it to me) It literally tore me apart. But my question is; If you are a cheater, Why do you do this? Why can't you get out of a relationship honestly ...

A.   28 November 2010: They do it because no one judges. No one calls cheaters out. Friends don't stop being their friends, or tell the victim of cheating. People knowingly sleep with attached individuals, and don't care that they're stealing someone's affection. ... (read in full...)

My girlfriend wants my baby to remember me by

Q.   ok im going out with this girl in new york but im moving to florida and were in love and she wants to have a baby that she can keep so it like a piece of me i cant even tell my parents anything how would i tell them how would i tell her mom i dont ...

A.   28 November 2010: For the love of God, do not listen to her. 1) You will owe child support if she ever decides to collect. That can add up to a tremendous sum of money, especially if she turns up after a few years. Just because she says she doesn't want it now, ... (read in full...)

My boyfriend keeps referring to the issues in my life as "baggage"1

Q.   I'm going through a tough time right now and need some advice. I am In love with a man who constantly refers to the things going on in my life as baggage. To break it down these are the things he has issues with and how I'm dealing with them. Firs...

A.   28 November 2010: I'll break this down by issue, but with one additional thought - he's probably seeing the combination of all of these as a very bad sign about you, which is really what tips the balance from "issue" to "baggage" in his mind. Also, I'll assume "... (read in full...)

International Day of Tolerance

Q.   I am sure there are some who know what day the 16th of November is, and I am also sure that there are some who don't. The 16th of November was declared the 'International Day of Tolerance' and its purpose is to spread peace amongst all races and ...

A.   27 November 2010: "Spirituality" may have a meaning, but far too often I've seen it used as a way to claim some higher purpose to doing whatever someone feels like at the time. Yes, that happens to every philosophy or religion; my point is that holding ... (read in full...)

He wants kids but I don't, sick of his nagging

Q.   i'm 22 years old and my boyfriend that i've been with for 3 years wants to have kids...and he keeps naggin me about it...i don't know how to tell him that i dont really want kids..... at all... well idk mayb wen im like 40 but im young and i luv the ...

A.   27 November 2010: 40? I hope you were exaggerating for effect. Female fertility hits its peak at 27. Things start to get rougher in your 30's. At 40 you could very well find it difficult to conceive, and the kids will be more likely to have disorders like autism ... (read in full...)

I was overweight as a child, now I feel I'm ugly. What is pretty?

Q.   Hey I really need a good bit of advice to get me out of the funk I am in. To give u some background: at school from age of 10 to about 16/17 I was v.overweight and not very pretty. I was picked on but never picked to go out with! Boys used to alw...

A.   27 November 2010: The power of good looks is very real, but very fleeting. Ask yourself, what else do you have of worth? Is there anything you don't have, but could develop? Obviously, having never met you, I couldn't say what, but here are some ideas - sense of... (read in full...)

Will talking about intimate subjects cause a problem in our marriages?

Q.   Hii...I am married and happy.I found a guy who is my close friend.We share couple of intimate topics.He is also married.We feel that we are getting attached and loving eachother.I too feel to spend the max time with him.though we never met just that ...

A.   27 November 2010: It might. If your husband is not your primary source of emotional satisfaction, it's easy to convince yourself you've fallen out of love with him - or to do it for real, and you'd have only yourself to blame. It's "emotional cheating," and it puts ... (read in full...)

Why do guys pretend to be someone else to get you to talk to them?

Q.   why would guys who like you pretend to be someone else to get to talk to you? ive had a few guys do this to me now and i click on straight away when they pretend to be someone else....

A.   27 November 2010: For the same reason you wear makeup, heels, and a pushup bra, or shave your legs. First impressions are important, and men are largely convinced that they have to show that they are funny, confident, and experienced within the first 30 seconds of ... (read in full...)

I want to stop being rude!!!!!!!!!!!!

Q.   ok, so here is the deal im gettin married in less than 30 days. lets call her miss bee, well miss bee and i have been together going on 10 years. i love her deeply, we have two sons and have been together since high school. ok so my ? i have been ...

A.   27 November 2010: Not sure what you can do about being on the phone, but whenever she gets home, before either of you says a word, grab her and give her a kiss - 5 to 10 seconds long. Hold her close while you do it. Should have a pretty calming effect, and you ... (read in full...)

She gave me her number, what's the next step?

Q.   I have started a course a couple of weeks ago and there is a girl on it who I really like. I want to ask her out but I'm shy to do that so what I did was I talked to her during the breaks on the course to get to know her and see what we have in ...

A.   26 November 2010: Who cares what her intentions are? Make a move. Force yourself to act against your shyness. How lonely would the world be if we could only ask out girls who already reciprocated our affection? The vast majority of relationships start as people ... (read in full...)

There's always someone out there who is better looking, more intelligent, etc.

Q.   I feel very inadequate. My boyfriend is attracted to another girl. She's more intelligent than me, more beautiful (her face is better looking than mine), more physically fit, and more socially skilled. I don't know what to do about it. I'm ...

A.   26 November 2010: I hate tearing someone down to build another up, but just to point out - her being more intelligent does not matter much, unless he's also way smarter than you are. Really, once a girl is smart enough to hold a decent conversation, female ... (read in full...)

Is it true that honesty in a relationship is the only way to experience true love?

Q.   People lie everyday believing that sometimes lies are necessary to protect someone's feelings. But do lies lead to an emotional disconnection with the person being lied to? Are lies barriers to true intimacy and growth within a relationship; even ...

A.   26 November 2010: Depends on the lie. There are white lies ("Of course you don't look fat.") and there is flat-out romantic fraud ("I'd never cheat on you.") Just remember what the two of you signed up for when you became exclusive. To use the above examples... (read in full...)

I don't like the idea of anal sex!

Q.   My boyfriend wants to try anal sex, but i just don't like the idea of it. Is it uncomfortable, or anything? Or should i just not bother trying it :/...

A.   26 November 2010: It's up to you - just as a reminder, this may be a dealbreaker for him. You have a duty to yourself not to exceed your own limits, but that imposes no duty on him to stay with you. Doesn't make him a bad guy, or you a bad girlfriend, it just mea... (read in full...)

He's a good man but has commitment issues

Q.   My boyfriend broke up with me on Nov.19. He said our relationship was not what he wanted and that he really does'nt know what he wants. He is 49 years old and never been married. The longest relationship was 3 years. The love this man very much, so ...

A.   26 November 2010: I can offer one possibility, but I'd give it only a slim chance of working, so don't get your hopes up. You'd probably still be better off moving on. Relationships are as much about economics as about romance. Guys like that, decent men who don'... (read in full...)

Seeking advice. She got pregnant, we're not together, now what?

Q.   I need some perspective on pregnancy towards what I should do. I was dating a woman for a few months, we were practicing safe sex, but a couple of times we didn't. She got pregnant, and decided to keep it. We broke up around the same time. That was ...

A.   26 November 2010: Just want to second KC100's opinion. She clearly gets it, and has covered almost every point adequately. The only point I would add is that if you are not in a relationship with the mother, she is going to start bringing home guys she's dating a... (read in full...)

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