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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...

< Prev89101112131415161718Next > [38 pages, 1485 answers]

We talk on phone but never on facebook. Why?

Q.   Hi everyone, i appreciate u guys alot. Just have a quick question i need answers to. My boyfriend and i are very much in love with each other, we are both on facebook, but he never posts on my wall or say anything to me on facebook, he talks to ...

A.   3 May 2011: He probably just doesn't want his girlfriend-talk aired out publicly. Either its sexual in nature, or its lovey-dovey, or its otherwise the kind of talk he wants kept private. If he doesn't use the chat function, it's because he wants to say those ... (read in full...)

It is domestic abuse. So why would some try to blame the victim? What's their mindset and the payoff for doing it?

Q.   i work with T who has recently been subjected to domestic abuse, and is still having this happen to her, at home. But something happened this week, people talking behind the back of T. And it has shaken my trust in some of my co-workers. Am i m...

A.   3 May 2011: Had a response all thought out, but Cerberus and MishMash have already said it, and better than I would have. So I'll just second what they said, and add a bit here. You hear it all the time from abuse victims, male or female, that they hate how... (read in full...)

How do I deal with my sadness and frustration at still not being married?

Q.   I envy my friends that are married. Well except for the ones that are in bad marriages. I dreamnt of getting married ever since I was a little girl. I have been engaged a couple times in the past but the relationships didn't last because those guys ...

A.   3 May 2011: Alright, we're getting somewhere. We see what you have to offer, but it needs to be examined under the light of what men value, and what is "wife-valuable" versus what's "girlfriend-valuable." Also need to consider how effectively you advertise ... (read in full...)

What's the secret to attracting a woman?

Q.   Please tell me what REALLY TURNS ON A WOMEN. What gives her that spark to feel so attracted she'll jump into your arms?...

A.   3 May 2011: Well, there's no one "secret" to it. But it's easier than a lot of people think. Just remember these two principles and you should be able to figure things out. 1) Observe actions, not words. What a girl says she wants is meaningless, it's who... (read in full...)

How do I deal with my sadness and frustration at still not being married?

Q.   I envy my friends that are married. Well except for the ones that are in bad marriages. I dreamnt of getting married ever since I was a little girl. I have been engaged a couple times in the past but the relationships didn't last because those guys ...

A.   2 May 2011: @ Anon: Hmmm. Perhaps your area just has a different social situation. Things like different age groups or gender ratios can affect the situation. I did specify young men - under 27, most (not all) guys have a tough time with women. A lot stil... (read in full...)

Where have all the good men gone? Any suggestions on how to find them please?

Q.   I've been actively dating for the past year. Overall, I've been extremely disappointed by the experiences I've been having. I've found many to be extremely selfish, immature, and have no respect for women. I've found that some men treat women li...

A.   2 May 2011: Are you presenting yourself as a quality woman worth investing in? Emphasis on the "presenting" part. Without knowing anything about you, I could say that whether you're a saint or not, failing to effectively make these qualities known would doom ... (read in full...)

Penis size insecurities......

Q.   OK, so we've seen the barrage of penis size questions. Got me so curious I decided to actually measure mine. What I encountered was that it may be impossible to get an accurate measurement because there are probably 13 ways to measure it. I know ...

A.   2 May 2011: Hmmm. As an engineer, I'll have to say I am fully in favor of developing a universal measurement standard here. All the anthropometrics data seems to be missing this information. In practical terms, measurement should be in average and maxi... (read in full...)

Bothered by the idea of losing my Virginity to a non-virgin....

Q.   Hi all, Just gonna be simple about this. I am a 17 year old boy who wants to save my virginity for marriage but I am bothered by the idea of losing my virginity to a non-virgin. I would just feel slighted in that I wasn't their first and they d...

A.   2 May 2011: This is a normal way to feel. Now, on the one hand, it's impossible for every virgin to lose it to another virgin, simply because some people sleep with more than one virgin in their life. So if you're planning to hold out for another virgin, ... (read in full...)

My Depressed boyfriend wants space. Can anyone tell me how to get through all this?

Q.   I have been with my boyfriend for 3 plus years now. He's had a history with depression and has had episodes where he'd leave for several hours or a day. He recently went through a custodial fight with his ex wife over his kids and lost. She took...

A.   2 May 2011: Short term: Take words out of the equation. Touch would be a much better way to deal with things right now. People seriusly underestimate the effects of simple non-sexual touch. It's a very effective, primal way of communicating love that affects ... (read in full...)

How do I deal with my sadness and frustration at still not being married?

Q.   I envy my friends that are married. Well except for the ones that are in bad marriages. I dreamnt of getting married ever since I was a little girl. I have been engaged a couple times in the past but the relationships didn't last because those guys ...

A.   2 May 2011: I'm going to try to point out the issues with a few selected statements, then point you in the right direction. "Plus it seemed like they wanted to marry my body instead of marrying me for my 'sweet warm hearted' personality." You need both y... (read in full...)

Should I become a total jerk for my own advantage ?

Q.   My ex-girlfriend dumped me three times and it's been one year since she dumped for the third time for small reason. I have heard that girls always find nice guys easy target to be dumped and retaken , is it true? If it's true, than why not should I ...

A.   2 May 2011: Chicks don't like assholes because they're mean and abrasive, they like them because they're confident and outgoing. Girls like consideration and kindness, they just like confidence more - enough, in many cases, to put up with all kinds of nasty ... (read in full...)

Should a guy really forgive a girl for being rude because she is on her period?

Q.   Is a woman's cycle really a reason to forgive her sudden bitchiness? ...

A.   2 May 2011: A woman is allowed to demand forgiveness for her PMS attitude if she forgives her man for being a horndog caveman when he has an erection. Or, in all seriousness (since tone doesn't carry well over text), people have self-control and ought to... (read in full...)

Do you think it's disprespectful for a guy to dance with another girl at a club?

Q.   do you think is it disrespectful for a guy dancing with any girl in the club while he has a girlfriend? and telling his girlfriend" hey baby im going out with my boys, then ofcourse i'm not gonna dance with my boys over there, only dance, but not ...

A.   28 April 2011: I don't, personally. I'll dance with girls while I'm in a relationship, and I don't mind if the girl I'm with goes out dancing, either. We know who's coming home to who. But it's not what I think. Are *you* comfortable with him going out dancin... (read in full...)

I don't feel the love between us anymore

Q.   I hate the fact that my husband has to work closely with a very good looking, actually hot looking girl. I'm very possessive and jealous type. I ask too many qs to my husband. I'm constantly suspicious. I also have self esteem issue, weight ...

A.   28 April 2011: I think you're inventing problems where there aren't any. It probably has something to do with the stress of a 6-month-old baby. That can mess with your perception - where previously you'd see him on his phone and know he's working hard to ... (read in full...)

Met a nice girl, but she's sending me mixed signals! We have a great time together and then, she won't pick up my calls. Should I ask her what's going on?

Q.   A few months ago I met this really nice girl on my course. We got chatting and I asked her if she'd like to go for lunch one day. She agreed and we had a great chat, got to know about each other and she even mentioned that I should go visit her in ...

A.   26 April 2011: Girls always find time to return calls for men they're interested in. They will make time, and they won't forget,no matter how busy they are. I wouldn't get your hopes up. That said, it can't hurt to try one more time. Call up (or meet up in pe... (read in full...)

So, being in a FWB situation, I'm wondering if these signs mean his commitment-phobia is starting to go away-or am I wasting my time?

Q.   I am having a friends with benefits relationship with a man. Before we started sleeping together, I knew he had been burned in relationships before and didn't believe in commitments.... that he only "hangs out" with girls. I got out of a ...

A.   26 April 2011: Guys are only very rarely willing to change a FWB situation into a relationship - generally, that situation completely tanks a man's view of that girl as relationship material. I think this sounds like the beginning of an exception, though, ... (read in full...)

How do I overcome my status as a "divorced" man? It seems women think I'm damaged goods!

Q.   Okay, so I joined match.com, and I'm a little dispondant. I'm divorced, I was treated badly by my ex who was emotionally and physically abusive to me, and after trying everything I had to leave for my own safety. I have ticked the divorced box...

A.   26 April 2011: Dating sites are a numbers game. Unlike in real life, a person can quickly compare hundreds of people to their 500-point checklist, cross off anyone who doesn't meet all criteria perfectly, and still have leftovers. It's kind of dehumanizing, if ... (read in full...)

Should I play hard to get or just be myself?

Q.   okay so iv been texting this guy for a couple of weeks now, he works with a couple of my friends and iv seen him before, a couple of times, but i have never actually spoke to him face to face. Im worried that if i text too much or come across as ...

A.   25 April 2011: There's no reason it can't be a careful balance of both. You can "play" without "playing games," and be yourself the whole time. But there's a lot of fun in the chase, so long as its done with both people playing in good faith. Playing hard to ... (read in full...)

Did he just say those things because we were having sex?

Q.   my boyfriend and i have been together for 6 months. We are both grown adults. We have discussed love and we both feel that we love eachother, but neither of us ever say "i love you" to eachother (because we are both afraid of heartbreak) last night ...

A.   25 April 2011: Sounds real to me. Some guys have a hard time with compliments due to bad experiences with girls when they're younger. They mistakenly assume that you can compliment a girl to make her like you, and are roughly disabused of that notion as teena... (read in full...)

My feelings have went flat toward boyfriend, is this normal?

Q.   Hello all. I think i need some advice..its always the same issues with me but they get better...then come back haha. I've been with my man now for nearing a year and Im 18years old. At the beginning of the relationship there was butterflies and ...

A.   25 April 2011: It's hormones. Your hormonal cycle, throughout a day and throughout a month, have a great deal to do with the kind of behavior your find attractive. It's easy to get caught up in thinking it's determingin the kind of man you find attractive (like ... (read in full...)

One date, I want to buy her a small gift, is it too soon?

Q.   I recently met a girl and we seem to get along great (common interests, fun to be around, laugh alot) even though we've only been on one date so far. We've talked on the phone quite a bit and texted. We have wanted to get together again real soon ...

A.   25 April 2011: Don't get her anything yet. This early in the relationship, gifts only create more pressure for both people. It almost comes across more as a bribe than as a gift. This is also why I usually advocate going dutch on the dates until you're more ... (read in full...)

I can't make her cum with fingers or oral, and I've got no rubber for sex...how do I find her G-spot?

Q.   i can't seem to make my gf cum by my fingers... she doesn't let me touch her clitoris cuz she says it is too sensitive..we can't do oral either cuz she isnt comfortable yet and we have no rubber for sex.. any tips other then the g-spot because i can'...

A.   25 April 2011: I'll echo the sentiment that you are too young to be having sex. Even if you can get a rubber, don't do it just yet. However, for future reference, you don't have to touch the clit directly to stimulate it. You can stimulate the clitoral hood, a... (read in full...)

I need creative ideas for a date for my husband and I!

Q.   I need help on a date idea for me and my husband. We have been having ALOT of problems lately and I have decided for ME TO TAKE HIME on a date. He has told me I’m boring before and that is b/c i probably am. I'd much rather stay at home than go out ...

A.   22 April 2011: Good for you taking the steps to make things work. And good for you, hearing criticism and working on improving things rather than getting upset about it. Your husband's a lucky man. The "boring" comment and the bickering might tempt you to rea... (read in full...)

How can you tell if a guy only wants sex or does he really care about you?

Q.   Hi guys. Can you tell me how you know a guy only wants to sleep with you? Are there signs, things he does, says, etc. that shows you he only wants sex with you? And if he really cares about you as a person and has feelings for you besides the...

A.   22 April 2011: It's easy to fake an interest in a girl's personal life - basically the male equivalent of faking an orgasm (make the right noises at the right time and they'll believe it). Further confounding the issue is that a guy who likes you for more than ... (read in full...)

Does anyone ever feel sexually inadequate when they know their partner has had many more partners before you?

Q.   Does anyone ever feel sexually inadequate when they know their husband/wife/girlfriend/boyfriend has had many more partners before you? I'm in a very loving relationship with a wonderful man. We've discussed marriage multiple times and we're both ...

A.   22 April 2011: If a guy only wants to be with you for one night, or a short fling, your lack of experience and skill in bed is an issue. If a guy genuinely wants to be with you for a long time, lack of experience is not a problem (and in fact, is probably a good ... (read in full...)

I don't know how to help him be the person I know he wishes he could be?

Q.   My best friend who i grew up with has had so many problems that effect his daily life, the main being when he was younger he had to have ear ventilation tubes and this has effected his speech a lot. He has a stutter and takes a while to get his ...

A.   21 April 2011: My brother had the same procedure done, actually, and with the same result. He struggled for a long time with it, and still has a very distinctive speech pattern. It helped him a little to deliberately slow down every word a little, but the ... (read in full...)

How to handle the question about previous relationships?

Q.   hi everyone, i was on a date a few days ago, and the conversation was going well untill the girl asked me when my last relationship was. im a 26 year old guy, and i was honest i said that i had never had a girlfriend before. she seemed horrified by ...

A.   21 April 2011: Most people judge others very strongly on their past. For a lot of women, this includes assuming there is something wrong when a guy doesn't have any previous relationships. This generally goes away once they've gotten invested in a relationship ... (read in full...)

How much is too much when it comes to honesty?

Q.   Dear Cupid, Currently i'm in a relationship for 4 months with this girl i met...the thing is when she asked about my past, i only told her that i broke up with a girl once before about 2 yrs back..i never told her that a year after that i got...

A.   21 April 2011: No reason to list rejections, unless she asks about rejections. We all have those, they're part of life and I don't see why you would even keep track. Certainly, never lie, and never withhold information that would be pertinent to her happines... (read in full...)

Why is my boyfriend suggesting all these sex improvement operations for me?

Q.   Been with boyfriend for 10 years, have always been there for him in every way. I take care of myself financially, stay fit, work out four days a week, dress sexy, do what I can to keep things exciting. The other night he brought up me having a ...

A.   21 April 2011: Depends on how he brought it up. You don't want to punish him just for expressing himself, but at the same time if he's going to be suggesting surgery, he needs to be doing so with the utmost respect. Frankly, it's hard to be respectful when ... (read in full...)

Marry former porn actress?

Q.   There is an organisation for former porn actresses called Pink Cross. These women now won´t have sex any more before married. The question is: Would you have married a former porn actress if you knew she had quit porn and now take distance from this ...

A.   21 April 2011: I'd certainly be willing to be friends, talk to her, work with her, or otherwise treat her as a human being. But not date her, sleep with her, or marry her. Partly, this is due to my aversion to meaningless sex (I've only ever had sex in long-ter... (read in full...)

What is the mind of a woman like?

Q.   if a woman suggests sexual activity to most any man, he's willing, probably eager, and more than likely thrilled. If most any man suggests the same to a woman, she'll say no, probably be offended, and very likely will decide that he's a shallow ...

A.   21 April 2011: A number of your basic assumptions are wrong. Nothing to be ashamed, many men much older than you have the same assumptions. Best to get them out in the open and work to correct them. It can be very helpful to have some accurate generali... (read in full...)

Does anyone have any clue what might be putting guys off or if I'm doing anything majorly wrong?

Q.   This Is probably a question that gets asked alot but I figured it wouldn't hurt asking. I've never had a proper boyfriend in my life and when I talk to people about it they tend to say things like you havnt met the right guy yet. But lately I...

A.   17 April 2011: People have a very hard time assessing their own attractiveness, even down by individual traits. I'll try to comment on what you've listed, and on whatever I can extrapolate from that, but if any of it sounds grossly off-base, just discard it as ... (read in full...)

Please rate the experience for me.

Q.   I'm 17 still a virgin, I think of it as a major accomplishment. I'm young and I'm not super model gorgeous but I'm very pretty people are always shocked when they find out I'm a virgin and they never believe me. My friends all not virgins keep ...

A.   16 April 2011: Good for you on holding to your principles. It can be tough to do, with peer pressure and all, but it's good and worthy of respect. I can't rate the first time from the female perspective, but I can tell you that whether it's the first time or ... (read in full...)

Must a guy make the first move?

Q.   I have known a girl for sometime now. she likes me but pretends she don't. I want to be sure she likes me before making a move. Must a guy make the first move?...

A.   16 April 2011: In short, yes, you have to make the first move. Unless you're devastatingly handsome or fabulously wealthy. Making the first move takes confidence, anyway, and confidence is sexier than money or looks. Why do you have to be sure she likes yo... (read in full...)

Would adding her on Facebook put us in the dreaded "friend zone"

Q.   Alright kind of a long question here. Alright, so there was this girl who lived in the room next to me in residence at university and about 2 weeks ago she mentioned that she and her boyfriend had broken up but she seemed to be over it from what I ...

A.   16 April 2011: Don't worry about missing your shot. Everyone hesitates. What's important is that you learn from this and become a better person. Facebook will not put youin the Friend Zone, hesitation will. Do not wait to ask her out. Do you know how many... (read in full...)

Questions about sex for the first time.

Q.   Hiya, last night i had sex for the first time with my boyfriend. Im already confused! On two occasions we had to use a new condom because it wouldnt stay on - is this normally what happens? Also, as it was my first time i assumed it would be real...

A.   16 April 2011: Good for you and your boyfriend. I hope you two enjoy exploring this side of yourselves. Anyway, for your questions. The condoms may be the wrong size, or you might be putting them on wrong. Google some instructional videos and watch them tog... (read in full...)

How much to shave.

Q.   I'm new to sex and everything and i wanted to know do i shave it all off keep some? i would ask my boyfriend but its embarrassing and i dont know what to do! ...

A.   16 April 2011: Look, here's the more important issue. If you're not comfortable enough to talk to your boyfriend about your pubes, you're not mature enough to be having sex. Would you avoid discussion contraception just because it's embarrassing? Ask him. So... (read in full...)

What would you do in the case of paternity fraud?

Q.   What would you do if you were to find out the child your wife/spouse gave birth to you was not yours? ...

A.   16 April 2011: I'm not sure if this is supposed to be hypothetical or not, but I'll answer as if you were asking what you ought to do. If you signed the birth certificate, or if you were married to her at the time of birth (birth, not conception), there's ... (read in full...)

Do I deserve to be loved again?

Q.   I never been a real relationship... But a few months ago I met this guy online and we fell in love with each other... We became girlfriend and boyfriend... We see each other on cam often, spend hours talking on the phone, and I did show him my upper ...

A.   15 April 2011: Well, you've made an honest mistake here. It happens. What matters is that, rather than repeating the mistake, you pick yourself up, stand proud, and learn from it. This means securing some form of commitment from a man before you give too much ... (read in full...)

Do you think this will get "A's" attention?

Q.   I'm attracted to this guy lets call him 'A' but he seems shy so he has never spoken to me but gives this impression that he is also attracted. Anyways, his friends with this other guy we'll call him 'B' who i've spoken to once and he hangs round ...

A.   14 April 2011: Careful not to send B the wrong message. A lot of nice, friend-type guys can develop attraction for a girl once they get to know her, so be on the lookout for that, and don't give him the wrong idea. That would be a passable way to get into A's... (read in full...)

Tips for lasting longer

Q.   Hey guys I have a bit of a sex problem arising. I'm not going to say I am the most gifted at it by any means so here's the problem. I'm dating this girl who has been with a few guys in the past and during sex not one of them has been able to las...

A.   14 April 2011: TranceDr has the right idea about not comapring yourself to past lovers. That way lies insecurity and unhappiness. But, the goal of lasting long for its own sake is a fine one, so here's some ideas. Long term, your best bet is to train yourself... (read in full...)

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