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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...

< Prev1314151617181920212223Next > [38 pages, 1485 answers]

My boyfriend won't celebrate Valentine's Day and I'm disappointed!

Q.   I've been having problems with my boyfriend, he smokes (cigs), drinks (even though he's underage), and uses very dirty language. I've often felt that he is dragging me down to his level. Recently, I moved out of my parent’s house into an apartment ...

A.   10 February 2011: You say he's smoking, drinking, and dragging you down to your level. He's mooching off you, and I'm willing to bet your parents hate him. He's had "many" girlfriends despite being 20 or younger, and the breakups were bad enough that he has a ... (read in full...)

Where does one draw the line between romantic super boyfriend and needy co-dependant?

Q.   How can I be there for my girlfriend without being smothering? I'm having trouble, I want to be supportive, Loving, caring, sensitive, and kind to my girlfriend. I Love her very much and I also like doting on her. I like giving her attention an...

A.   10 February 2011: When in doubt, err on the side of not being available enough. Better to have that air of detachment than to smother her. The operative part of that sentence is "when in doubt." If you know what you're doing, be as supportive as you like. ... (read in full...)

Should I be concerned after a bad proposal?

Q.   My bf and I have been dating for 20months. I have a long history with him. We were friends before we dated for about 8yrs. I love him very much and have been wanting him to ask me to marry him. He actually proposed to me two days ago. It definite...

A.   8 February 2011: Thanks for the follow-up. Good luck with the coming engagement and marriage. If you can continue to examine your actions and motivations the way you did here, you will do well.... (read in full...)

Are there good guys out there? The ones I've found so far aren't

Q.   Recently I have started going to a counselor because of these “mini-depression episodes” that I have. This term “mini-depression episodes” is a term that I use to describe the times that I am uncontrollably sad, irritable, and hopeless. I feel that ...

A.   8 February 2011: Gotcha on the "not necessarily a relationship thing." Two things though. One, you're not the only one who could be telling people about the guy you're hooking up with - I guarantee he's bragging to his buddies. Word gets around. Two, you'd be... (read in full...)

Should I be concerned after a bad proposal?

Q.   My bf and I have been dating for 20months. I have a long history with him. We were friends before we dated for about 8yrs. I love him very much and have been wanting him to ask me to marry him. He actually proposed to me two days ago. It definite...

A.   8 February 2011: The fact that he proposed at all should be enough. Yes, it's nice if it's romantic - but what's more important is that you have your own story, and your own future. I'm sure you realize just how overly-entitled it's sounds to want a proposal... (read in full...)

Are there good guys out there? The ones I've found so far aren't

Q.   Recently I have started going to a counselor because of these “mini-depression episodes” that I have. This term “mini-depression episodes” is a term that I use to describe the times that I am uncontrollably sad, irritable, and hopeless. I feel that ...

A.   8 February 2011: "Hooking up" is by it's very nature not exclusive. You can ask for an exclusive relationship, but unless you're explicitly going out with someone they will generally assume they can get more on the side. Moreover, guys rarely respect booty-calls ... (read in full...)

I've got the French maid costume, but what do I do after I put it on?

Q.   My boyfriend has told me before that one of his fantasies is for me to dress up as a french maid. As we are at different universities we hardly see each other at all any more, so I thought I'd surprise him when I go to visit him next. The thing is...

A.   7 February 2011: Draw it out as long as you can. Anticipation is as sweet as the real deal. Play the role to the fullest. For instance, cook something, and bend low over the stove - or just put all the ingredients on the bottom shelf of the fridge. Or make a ... (read in full...)

My friend can't have kids? Can she carry mine?

Q.   My friend just found out she can't have kids . She's very upset and she's 16. Can my friend carry my baby even if she can't have kids?...

A.   7 February 2011: Ask your doctor, and your friend. Seriously, even if anyone here was a qualified physician, you haven't told us anything about *why* she can't have kids. For instance, as fi_the_tree pointed out, if she's just missing eggs, she may be able to ... (read in full...)

Why are women devalued after sex but not men?

Q.   Why is it that after sex , a man devalues a woman and views her as " cheap stuff " or " slut " but you don't hear women calling men " cheap " ? Why is it that for a woman to be able to make the man stay interested in her, i.e. want her not jus...

A.   7 February 2011: "Real love is given freely with your whole heart and soul, without the fear that you need to compete." This question is about the earliest stages of a relationship - first week or two, and the need to wait for sex. Sure, once the relation... (read in full...)

How did my boyfriend know that I was having my period?

Q.   this is a really awkward question to ask, but my boyfriend today asked me if i was on my period.. when i asked why he just said answer, my first day was today so i said yess??? and he said i knew it! I was like oh was i being moody? and he said oh ...

A.   7 February 2011: If it was your behavior, he probably wouldn't say it was - he would lie and claim it was something else. I've never heard of voice changes during periods. Still, there are other signs he may have caught on to. If you normally wear shorts o... (read in full...)

My boyfriend always think I'm flirting and can not accept that I am bisexual

Q.   I'm female and I am bisexual. My boyfriend knows it! I don't deny it and I never will. He hates the fact that I am and he even told me so. I make it clear to him as much as I can that I love him and no one else. However, everytime we are with my f...

A.   7 February 2011: Well, I can't tell him what to do, since he's not the one writing in. So I'll try to explain his motivations, then you can decide what to do with that info. First off, really examine whether or not you are flirting. A lot of girls (and guys, fo... (read in full...)

Protocol on going to strip clubs

Q.   Hello guys, do u think is it ok for the guys while they are in a relationship and want to go strip show club either with you or his friends and let u go with your female friends too? and also i asked him if he go to striptease club before a...

A.   7 February 2011: Re: Guys in relationships going to strip shows If you're both comfortable with the thought of each other going to strip clubs, then go for it. I don't think it's conducive to a healthy relationship, but if you're both fine, then that's your cal... (read in full...)

Whatever happened to holding hands and watching the sunset?

Q.   So, alot of things have been hard to adjust to since I got out of the Army. Not the least of which has been dating, or...not dating, I suppose. I like to think I'm a nice guy, outgoing in public, but private at home. I own my own house, and c...

A.   7 February 2011: Girls are used to being treated poorly - if you don't believe that, nex time a girl says that a guy treats her like a princess, start asking questions about how often her boyfriend makes her cry, cancels dates, or gets blind drunk on weekdays. ... (read in full...)

If you live together first does it hurt your chances for marriage?

Q.   I'm separated, soon to be divorced after a long term marriage and am just beginning to date again. A lot seems to have changed since I was last single. One of the things I don't understand is that at lest where I live, it seems that everyone wants ...

A.   7 February 2011: Stanford did a study on this a few years back, saying that yes, cohabitation significantly increases the chance of divorce - not that the chances are exactly low anyway, as you point out. Of course, marriage isn't even a commitment anyway - as you... (read in full...)

Why are women devalued after sex but not men?

Q.   Why is it that after sex , a man devalues a woman and views her as " cheap stuff " or " slut " but you don't hear women calling men " cheap " ? Why is it that for a woman to be able to make the man stay interested in her, i.e. want her not jus...

A.   4 February 2011: @ Anon "A lot of what you say holds..." It's entirely possible to see a woman as a real person and still realize that sex and romance are competitive - there is winning, there is losing, and there are competitors. Trying not to say "players... (read in full...)

My parents told me the girl I'm dating isn't socioeconomically acceptable!

Q.   Dear Cupid, I'm 24 and i really love my girlfriend so2 much...however, my parents don't approve of this girl.. they consider her as not being of the same level socioeconomically....i don't care what her parents work as, or what type of house she ...

A.   4 February 2011: CaringGuy is right, you have to be willing to make a firm decision here. Decide what is more important. That said, you can try to dig up the reason they're concerned - is it a status thing? Or are they concerned about the future mother of their... (read in full...)

I only have $50 to spend for Valentine's Day!

Q.   So I'm broke for valentines day I just lost my job and I don't know what to do we don't live together so we can't do anything like breakfast in bed or a romantic bath help please! I only have like 50 bucks thanks in advance !...

A.   4 February 2011: If you're not in your parents' house, you can spend the night together and have breakfast in bed. Pay your roommate $20 to leave the house for a while and then sleep on the couch. They can go see a movie while you stay in, maybe rent one. Or, i... (read in full...)

We love each other but lately we're arguing all the time

Q.   Ok so I've been dating this guy for almost 3 years now. About a year ago, we started talking about getting married...but he recently told me he wants to wait until he's done with school and has a job (we are both mid-twenties, I graduate in April, ...

A.   4 February 2011: Stress will do that to a person. It makes folks pick a fight, often over trivial thigns, because they're at their wits end. But it takes two to fight. Don't engage him when he's in that kind of mood. It causes rational points (for instance... (read in full...)

Do man usually lose their sexual self after 40?

Q.   Well, I really would like to hear as much opinion as possible. Do man usually losing their sexual self after 40? Or this is rare? How common is the diminished sexual desire, and non medical based erectile problems? Please help me out.....I was ...

A.   4 February 2011: There are a lot of factors at play. One is that, yes, after 35 or 40 the parts just don't work as well as they used to, he has less testosterone and other sex hormones to give him his sex drive. This can be countered by regular excercis... (read in full...)

Why are women devalued after sex but not men?

Q.   Why is it that after sex , a man devalues a woman and views her as " cheap stuff " or " slut " but you don't hear women calling men " cheap " ? Why is it that for a woman to be able to make the man stay interested in her, i.e. want her not jus...

A.   4 February 2011: Ooh, fun question. First, women are worse to each other about the whole "slut" thing than men are, generally. At least that's what it looks like to me. And putting out early for one person makes it a good bet (not a guarantee, but still a very g... (read in full...)

Should I have waited till marriage so it would have been more special?

Q.   dear readers, me and my boyfriend have been going out got four years now and well we have had sex and all. so really the thing imtrying to say here is that i always had this dream that i would wait untill marrige. or atleast be older than i was...

A.   3 February 2011: Waiting is a good thing, true. But it's not the tradition, the wait itself that is so important, as the reason behind it. Still, before anything else, you should be proud of yourself for really thinking on this, rather than just rational... (read in full...)

How can I reassure her she has nothing to worry about?

Q.   All my best friends are female, and this majorly bothers my girlfriend, who has major trust issues. I was wondering if there was any way for me to effectively ease her worries or is this something she has to deal with herself? ...

A.   3 February 2011: This isn't about trying to convince her - you need to let her know that, once you've promised to be faithful, your word is your bond. Keep your promises in all other aspects of life. And if she's still going to be insecure, let her know it's ... (read in full...)

Do men treat their girlfriends differently???

Q.   Do men treat their girlfriends differently? If so, why? I broke up with my ex just over a year ago. I thought I was getting over him quite well until I saw some photos of him on a social networking site with his new girlfriend. She talks of...

A.   3 February 2011: Yes, guys treat different girlfriends differently. Sometimes it's because we got older and wiser; sometimes just because we got jaded. I think both are at work here. With his last girlfriend, he clearly spoiled her... and they broke up anyway. ... (read in full...)

Why would a guy move slower, sexually, with a girl?

Q.   I'm 24F and I've been dating a 26M for a little over a month now and things are going great! We see each other a few times a week and we seem to be content with the amount of time we spend with each other since we both work and I go to school ful...

A.   1 February 2011: The public boner is mostly a function of testosterone levels. He's probably more high-T than some of the guys you've been with, and is therefore more easily aroused. That, and he hasn't been desensitized by his previous experiences. That's a good ... (read in full...)

Why swallow? whats the pleasure?

Q.   dear readers, i would like to ask the men out there and possibly the women why men like a girl to swallow their semen? why is it attractive to men to see there girlfriend swalllowing the product of their energy? some women say it tastes awfu...

A.   1 February 2011: It literally feels better. I'm not sure why in a physical sense, but it does. It's also wonderful in a psychological sense, being so loved, wanted, accepted, and most of all *desired* by a girl that she'll gleefully swallow. Sure, she's going to... (read in full...)

He wants a blowjob but I don't like doing it, what can I do?

Q.   i have been in a sort of relationship with a boy, we are both same age(17). at the start we were just good friends he would come up for a drink, then things started to change we would kiss at weekends and then i saw him during the week and we would ...

A.   1 February 2011: You're in a "sort of" relationship? What exactly does that mean? Make it an official relationship, then give it some time before you get sexual. If he's with you both for the commitment and the wait, he's a keeper. If not, move on. Now, on... (read in full...)

My ex has anger management issues. How can I get him to move on?

Q.   There's this guy in school whom I admired (a crush admiration only).. But eventually,i found out that he has anger management issues,so i didn't like him anymore,and so my classmates told me to distance myself a bit from him. But i was afraid t...

A.   1 February 2011: Alright, you really should have said no at your first opportunity. By saying yes, you gave him more to lose when things ended, and made things worse. Next time this comes up, keep that in mind. Do not let fear rule you, ever. It's possible... (read in full...)

Am I too slutty for a serious relationship?

Q.   So, I'm searching for a serious relationship. I've never had one. I know this guy who is really nice and friendly, but I only saw him as a friend... until two weeks ago saturday we went to a party and he held my hand and was really nice to me. I had ...

A.   1 February 2011: First off, in response to "I know what I'm doing," *no one* knows what they're doing. There's no shame in that. Anyway, putting out too early (oral and handjobs included) convinces a guy that he is not special, and you have probably done the same... (read in full...)

I've received messages from my boyfriend's ex. Is he lying to me?

Q.   My boyfriend went to visit his hometown a few weeks ago for a week after we had had a huge bust up and I thought we had finished until a few days after he left I spoke to him and we were ok. Since he's been back our relationship has been brilliant ...

A.   1 February 2011: He's cheated more than once - and more importantly, he knows that if he cheats on you, you'll keep dating him. He almost certainly did cheat on you again. In any event, if you love him, and his ex loves him, despite his cheating ways, odds are... (read in full...)

I think she wants me to pop the question but I'm terrified!

Q.   I've been dating my girlfriend for a little over a year. We have become very close over the course of the past year. Recently, she has let me know that she is ready to move onto the next phase of our relationship, i.e. she wants me to pop THE ...

A.   1 February 2011: Hmmm. The new info about the ex-girlfriend changes things up a bit. This does take the focus off the pressure on you and put it more on your own relationships. Keep it in mind for when you do think about marrying, though - and at least wait until ... (read in full...)

I think she wants me to pop the question but I'm terrified!

Q.   I've been dating my girlfriend for a little over a year. We have become very close over the course of the past year. Recently, she has let me know that she is ready to move onto the next phase of our relationship, i.e. she wants me to pop THE ...

A.   1 February 2011: The prospect of getting married should scare you, it's a bad decision. This has nothing to do with commitment issues (I doubt you have any such "issues" anyway, at least not enough to be worth apologizing for) - first, because you are capable of ... (read in full...)

The most difficult question ever: What is Love???

Q.   Last night my boyfriend asked my what does love mean to me. I told him it means everything to me .He said i dont understand. I told him its hard to describe love for me. Then he told me how can i love someone if i cant even describe what it is to ...

A.   29 January 2011: If he needs a quantitative answer, tell him love is funny chemicals in our brains that make us behave like idiots. It's evolution's own adaptive form of sexual attraction that leads to strong feelings of loyalty and affection, causing two people to ... (read in full...)

Whats the appropriate age for sex?

Q.   dear readers, i wanted to know when you people think is the appropriate age to have sex? i know you are supposed to when you and your partner feel ready, but is there a time that is t young? is 14 or 15 to young? what if you had been with your...

A.   29 January 2011: 15 is too young. I'd say 17 is the bare minimum, and probably best to wait until 19. Doesn't matter that you've been with a guy 2 years - in fact, I'd say add a year to guys' ages, making it 18 to 20 for them. If you're not ready by then, there's ... (read in full...)

How can I tell my mistress to get an abortion... NOW!

Q.   Hi. Just seeking some advice. I have been married for 7 yrs been with wife for almost 15. she's older than me by a couple of years (I am 37 my wife is 43 and my lover is 35). , but I think she is my soul mate. I cheated on her before this time, but ...

A.   29 January 2011: At this point, it's about damage control - never too late to start doing the right thing. First, the abortion isn't happening. It's legal in many states at this stage, and I suspect it's not a moral issue for your mistress any more than it is fo... (read in full...)

Sometimes I feel as if I have a room mate and NOT a wife!

Q.   Me and my wife have been married for 4 years and I have had lost my job and we had a baby and I have noticed that lately she has lost interest in sex, she has worked a lot more hours the last few months but here lately been saying I have a headache ...

A.   29 January 2011: Take her out. Do stuff together in the home, like cooking. Drop your kid off with someone else, share a few drinks and put on some music, then just talk with her. You have to warm her up for these things, can't just ask for sex right when she' ... (read in full...)

Am I wrong to be angry with him for making these money decisions without me?

Q.   am i wrong here? i have been with my boyfriend on and off for a year and half. he was getting a lump sum of money and we were going to get married sometime this year but i think thats not going to happen...anyways he got the money early today and we ...

A.   29 January 2011: First off, you get to feel angry, that's always okay. It's how you act that matters. Right now, it's his money, and you're not married. The fact that he's even spending money on a TV for the two of you is already very generous. And he made the... (read in full...)

Honeymoon & Birth control

Q.   My fiancé and I plan on not using protection on our honeymoon except for when she says it's time to start "being careful". That should be about the last few days of our week in Florida. She isn't okay with birth control so I will use a condom. Her ...

A.   29 January 2011: The chances are high. Condoms are one of the least effective means of preventing pregnancy - better than pulling out, sure, but not good enough. And the cycle is not a perfect predictor of fertility; it can vary depending on the environment, or ... (read in full...)

Are love and marriage a deadline?

Q.   Does anyone else think women now a days are more in love with the idea of "love" and "marriage" then they are with the true meaning behind it. I keep meeting more and more women who talk about marriage like a dead line rather then the importance of ...

A.   29 January 2011: While I agree with your assessment, and that it's a bad thing, in fairness to women they do have something of a deadline. Their youth and fertility are two of their primary "selling points" (if someone has a better term for this, please feel free ... (read in full...)

Drunk "I love you"?

Q.   So what do you think if someone rings you up or texts you in the middle of the night to say "LOVE YOU xxx" Is this a drunken expression of a deep emotional feeling, or merely a drunk expression! What makes people say "I Love you" at times...

A.   29 January 2011: I can't tell you how many people I've said "I love you!" to while drunk. Then proceeded to tell them why. And everyone else at Denny's. Or to the cops. This probably doesn't mean anything, unless you two have a history together. Go hang out... (read in full...)

How important is the ring?

Q.   She said "If I got an engagement ring I didn't like,or was to small I would return it and buy something I really liked." Part of me laughs at this the other part is scared out of my mind. Who would say something like that, I thought engagment was ...

A.   29 January 2011: This girl wants to get married, not be married. She wants a big party. This is one of the bigger warning signs out there - I'd bet good money that she'll turn into a serious bridezilla. Double or nothing she falls out of love and initiates a ... (read in full...)

Why do women often think too much into how to act with their guy?

Q.   Why don't girls realize how easy it is to be a "catch?" I see so many posts that involve girls who will resist some sexual acts, or just being sexually aggressive, because they don't want their partners to think they are a slut. That's just not ...

A.   27 January 2011: Nice article. Each of the points is true and, more importantly, easy to understand. What's missing, though, is the fact that a lot of guys are flat-out unreasonable (women, too, but this isn't about them). Everyone is prone to the "If this is ... (read in full...)

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