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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...

< Prev1011121314151617181920Next > [38 pages, 1485 answers]

Do you fantasize about other girls or your girlfriend?

Q.   This is a question for the males. For those of you with girlfriends/fiances/wives/partners etc do you always think of them when you think of sex and your fantasies? So when your maybe daydreaming or watever it is that gets you thinking, who a...

A.   25 March 2011: @ BettyBoup The key word in that phrase is "little." An overall insecure girlfriend is a pain - and that's before you consider the effect on her own happiness. Short version is that being a little insecure keeps a woman on her toes, givin... (read in full...)

Do you fantasize about other girls or your girlfriend?

Q.   This is a question for the males. For those of you with girlfriends/fiances/wives/partners etc do you always think of them when you think of sex and your fantasies? So when your maybe daydreaming or watever it is that gets you thinking, who a...

A.   25 March 2011: I'll fantasize about whoever. Pretty girl who walks by on the street, ex-girlfriends, Scarlett Johansson, they're all fair game. I'm pretty confident most guys are the same way. That said, two caveats. First, these are just fantasies, and I... (read in full...)

Help me to be more confident around girls

Q.   Hi, I was just wondering if you could give me some advice on how to become more confident and outgoing around girls. Im 15 years old, athletic, quite good looking and quite inteligent. Please give me help as it is really annoying me and I just want ...

A.   25 March 2011: This is a really, really broad topic, so I'll just give you a few pointers. Better to have a handful of ideas you will be able to remember and act upon than a complete dissertation you can't remember any of. Just remember, you weren't born kno... (read in full...)

I am concerned that my soldier boyfriend wants to use me for sex before his deployment, but I don't know how to tell him.

Q.   Hey All, My boyfriend is in the Army. He's deploying soon and I'm currently in a college a solid 7 hours away from him. I want to be able to see him before he leaves but since he has such a short window to be home, I have to miss school. Thi...

A.   25 March 2011: I think this skirts the fine line between "using" you for sex, and using sex as a way to spend time with you. Under normal circumstances, people can both spend time together *and* have sex. Guys like both, provided the girl is worthwhile. But... (read in full...)

I pushed him about commitment and may have pushed him away

Q.   A short question to help with a lengthy one...! A guy I really like has been unsure if he wants the commitment of a relationship, (we were seeing each other and it was going really well before he suddenly got all mixed up about it) and basicall...

A.   25 March 2011: The way you first start seeing a guy sets the tone for your future interactions, in large part because how you expect to be treated up front determines how he believes you deserve to be treated. By seeing him (sleeping with him?) you set the tone... (read in full...)

How can I get him to realise that he can't let his friends get in the way?

Q.   Okay, so.. There's this boy in my year that I really like.. I first liked him before Christmas last year, but he had a girlfriend then (which I didn't know about), he promised me that if and when they broke up, he'd go out with me. So we stayed...

A.   25 March 2011: "...he promised me that if and when they broke up, he'd go out with me." This is a *huge* red flag. Re-read it until you see that. He was keeping you waiting in the wings as a backup. And you were OK with that? You cheapen yourself by allowing... (read in full...)

Should I be angry at my boyfriend for sharing his fantasy??

Q.   Last night while I was in bed with my boyfriend making love, he asked me if I had any fantasies lately. I said no but asked him if he did. Earlier on ITR I introduced a little kinkiness to our sex life by talking about fantasies together to turn ...

A.   25 March 2011: It sounds like he started to say it in the heat of the moment, but caught himself at the last second - entirely understandable, our guard is (and *should* be) down during intimate times. It's the easiest time in the world to say something stupid. ... (read in full...)

He left me when I was a month pregnant and I never hear from him until a year later when he wants to marry me!?

Q.   Hi everybody,Please help!My boyfriend left me when i was a month pregnant.I take care of myseslf during all my pregnancy time.I had never heard about him and I did not know where he was neither.I took over everything on my own,no child support,and ...

A.   25 March 2011: Depends on the situation. If the pregnancy was accidental - or worse, against his express wishes - then you can understand why he would need some time to come to grips with things. Guys have zero choice regarding pregnancy, but are still expected ... (read in full...)

Troubled son--what do I do with him?

Q.   I have a 16 year old who I am now so ashamed off. He has really gone off the rails. I have been a single mum for many years and my current partner stepped into his life when he was about 6 yet he does not appreciate or respect him and keeps ...

A.   24 March 2011: Children of single mothers are significantly more likely to act act. This is a relatively extreme case, but it's one of the risks people take when becoming single parents, by choice or otherwise. In particular, a lot of kids have a very hard time ... (read in full...)

Is it weird that I don't like to kiss the guy I'm sleeping with unless we're in a relationship?

Q.   I've only been sexually active for the last year and a half, and I've only dated 2 of the 8 guys I've slept with. Nonetheless, I've come to realize that I don't feel right kissing the guy unless we're in a relationship. Is it weird that I put ...

A.   24 March 2011: I think the bigger concern should be the fact that you've been with 8 guys in 18 months. That's not a healthy lifestyle to get into. You may want to look into it. However, regarding the kissing question, it's unusual, but not really "weird."... (read in full...)

Sex is no longer on my agenda

Q.   I have been with my husband for 6 yrs, married less than 1 yr. I'm never in the mood to have sex. I believe this is due to that fact I have been feeling down lately about my body as I've put on a few pounds. But I also don't find my husband sexy ...

A.   24 March 2011: OK, two things to look at here. 1) Your body. Lose the extra pounds. Go on an exercise program. Join a gym, commit to going at a certain time. Bonus points for getting your husband to go to the same gym, especially if you do different workouts... (read in full...)

Am I really creepy to guys?

Q.   EVery guy i have a crush on ends up finding out and becomming creeped out. Am i really creepy to guys?...

A.   24 March 2011: You'll have to give us some more information. Can you list any specific complaints? Perhaps things you've done that you suspect may come across as creepy?... (read in full...)

Would a girl laugh at my penis when its not erect?

Q.   i wondering if my 6-7 inch dick (erect)is big enough to do the job? when its not erect its maybe about 2 inches. i kind of feel embaressed when its not erect. i feel like a girl would laugh when she felt it not erect....

A.   24 March 2011: It just means you're a grower, not a show-er. The first time a chick sees it, it will almost certainly be erect. After that it won't matter, they'll know what you have.... (read in full...)

Why are people so judgmental?

Q.   Why are people so judgemental? On here there are a lot of aunts and uncles, who seem to think that because a young questioner asks a question about love and relationships, they need to discourage this young person from being grown up and thInking ...

A.   23 March 2011: "One last query: Would you have answered differently had there not been an age displayed?" Nah, I'd have assumed from what you wrote that you were a teenager - or at least that you were referring to advice directed at teengers. If you changed ... (read in full...)

How do I overcome the awkward silence and show him an amazing time?

Q.   hi i am 22 years old and i will be going out with the guy abt 25-26 years of age for the first time..well he will be visiting my place for a day or two..and i live in a small city,so we dont have much to do around here like go skiing,or hiking..its ...

A.   22 March 2011: I don't know what there is to actually do in your town, but generally, anything that requires you to keep your hands occupied (drinking coffee, painting, driving, even playing video games if you're really desperate) will tend to make conversation ... (read in full...)

How do I change the way I am?

Q.   Hello, Recently me and my boyfriend have had huge fights, we have been together for 2 years, recently the fights just seem to be him having goes at me, pointing out all my flaws, calling me arrogant and other things. And he says that unless i ch...

A.   22 March 2011: I think you should take some time to figure out if the things he's mad about are real, objective flaws, or if he's just yelling at you and being unreasonable. If, after very careful consideration, you've decided you want to change something, the o... (read in full...)

Is it possible to predict before marriage that a couple's sex life will suck 5-10 years after they get married?

Q.   Almost every one of my guy friends who has been married for more than 5 years or so has told me their wife has lost almost all interest in sex. Many go for a month or two without it onb a regular basis. They also tell me about friends of theirs who ...

A.   22 March 2011: @ Chigirl and Aunty Bim Bim (awesome name, by the way): Never been married, myself. I've seen friends and family torn up by divorce, though, usually because they stopped keeping their wives interested, and their wives made little effort to help t... (read in full...)

Guys do you prefer to approach or be approached?

Q.   On a night out what do you think of a girl that makes the first move to approach a guy? Do guys prefer to approach the girl themselves?...

A.   22 March 2011: For most guys, it's a real event whena girl approaches. It makes us quickly assume the girl likes us, and wants us, and is a huge ego boost. That's because chicks rarely approach most guys. It's not so much that we *prefer* to approach, as it ... (read in full...)

Is it possible to predict before marriage that a couple's sex life will suck 5-10 years after they get married?

Q.   Almost every one of my guy friends who has been married for more than 5 years or so has told me their wife has lost almost all interest in sex. Many go for a month or two without it onb a regular basis. They also tell me about friends of theirs who ...

A.   22 March 2011: Short version: Are you getting married? Y/N If you answered Yes, your sex life is going to suck. Long version: After marriage, women have no incentive to have sex with their man. Either he meets their demands, or they divorce him and... (read in full...)

Where is the world going? And yes this does affect relationships.

Q.   "Where is the World going? And yes this does affect life and relationships." The original question received from an anonymous female in the UK aged 26 to 29 and called "Where is the UK going" inspired this article. And you might think this does ...

A.   22 March 2011: I'm going to respond to each of your points by number, for convenience. 1 - Change) Economic instability and societal instability tend to go hand-in-hand. There is a certain amount of mutual cause and effect here, but as for relation... (read in full...)

What does a man feel emotionally when receiving oral sex?

Q.   Hey guys....I read something once that "Giving a man a blow job is like giving a woman flowers" What kind of feeling does it give a man when she wants to give him a bj? Is it just a feel good sexual act or do you guys feel a connection with ...

A.   22 March 2011: During the act? Thoughts don't really translate into words. It's just awesome. Never gets old. After, though, is when I really think about how great it is. It's a great expression of devotion from a woman, and I realize that. It's reinforc... (read in full...)

Should I continue to pursue a relationship with a girl who is now going back to try and work things out with the father of her child?

Q.   I been talking to this girl for the past 4 months and when I met her she just gotten out of a relationship with a guy she has a daughter with. This guy lives in another state and about a month ago he came down to see his daughter and in the process ...

A.   22 March 2011: In general, you should never date single mothers, especially before your 40's. You will always be second place to their child, and you will never be rid of the father. You can do much better. However, the deciding factor in this case is that you... (read in full...)

How do I react to my 15-year-old friend who got pregnant...and wants me to be the godmother?

Q.   Okay, I got a text from my friend, who is only 15. She said that she was expecting a child, a baby boy, she was 23 weeks pregnant. The father and I both used to be best friends for a while. He is also 15. They're both in the year below me at ...

A.   22 March 2011: Two things: 1) Never, ever respond to a request for life-long commitment if it's given by text. If she really wants you to be Godmother to her child, she can ask in person. 2) Among other things, a Godparent promises to be responsible for ... (read in full...)

Why are people so judgmental?

Q.   Why are people so judgemental? On here there are a lot of aunts and uncles, who seem to think that because a young questioner asks a question about love and relationships, they need to discourage this young person from being grown up and thInking ...

A.   22 March 2011: I love it when people come looking for an argument. 1) Maturity is easy to fake. I know 30-somethings that do it every day. It is especially easy to fake your maturity to yourself - people think they're smarter and more mature than they actually... (read in full...)

I am a Christian in love with a Muslim, and I am afraid of alienating my family.

Q.   I've been in a LDR with my boyfriend for almost a year. I really love him and the time we spend together, our relationship just feels right to me. My only concern right now is religion, if it even is a concern. I'm Christian and he is Muslim. I'...

A.   22 March 2011: I think the biggest concern should be his family's reaction, not yours. He may be alright with your faith, but I'd be willing to bet his family would be very upset about it, and likely pressure him into leaving you. I've heard horror stories about ... (read in full...)

My bf and I have done everything but have sex, and he doesn't like to talk about it. Does that mean he doesn't want to have sex with me?

Q.   I am 17 years old and me and my bf have been going out for over a year now. I was wondering if anybody could interpret my bfs actions. He has me very confused. We have done everything sexually except actual intercourse. He is very shy but is happy...

A.   22 March 2011: It's possible, but more likely that he is just uncomfortable talking about it. This is especially likely if you're more experienced than he is. Maybe he was just raised in an enviroment where talking about sex was uncommon, or maybe he just doe... (read in full...)

I cant make a decision about our relationship!

Q.   Ok, i will keep this short and sweet(ish). I am a 24 year old girl and I have been in a stressful relationship for three years. I love this man very much, I know him inside out and he knows me just as well. However, we break up. A lot. And i...

A.   22 March 2011: "He has a quick temper but is also incredibly loving and attentive." For many girls, this is basically crack. It's dramatic and exciting and unpredictable. Most chicks are far more attached to those traits than to simple happiness or contentm... (read in full...)

Should I let this hate manifest and use it as a drive to push past her or is it unhealthy?

Q.   me and my gf just broke up recently after a very passionate year together. neither of us fell out of love until after the unexpected departure. we were even still in love after the break up. then she got a new bf 3 weeks after and im nothing to her ...

A.   22 March 2011: Hate is a normal and natural emotion. When it becomes an issue is when it doesn't go away; that's unhealthy. In the short term, hate will give you the energy to refocus your life into things that don't involve her, and the resolve to avoid contact ... (read in full...)

I don't think I can fulfill what my girlfriend wants from me!

Q.   My girlfriend said that I am selfish and a heartless person, because I don’t think about her first. She began to list all things that caused her to be upset. 1. Week 1: Saturday to Friday - I go to work full time from 8 to 5pm and take one class o...

A.   22 March 2011: OK, the long and short of it is that she is giving you crap just to see if you'll put up with it. All girls do this; she is an egregious example, but not abnormal. Consciously, she wants everything in the world - including the mutually exclusiv... (read in full...)

Guys: is this because you liked the attention or are attracted?

Q.   Hi quick question but guys only on this one please. Say you meet a girl out and you ask her to join you and the rest your friends that youre with when you move on to a different place (say met them in the bar but you are planning on going to another ...

A.   20 March 2011: Sorry, there's no way to say with this amount of information. Generally, a guy assumes that if a girl asks for his number, she must be *really* interested (since girls seem to expect guys to take all the initiative) - so we know he thinks you like ... (read in full...)

When choosing someone to marry, do you use your heart or your head?

Q.   I really need help... I have been with my boyfriend for more than 5 years. We have gone through so much together. We really had our trials but in the end what got as through is the foundation of our relationship. He's really my best friend. My ...

A.   17 March 2011: Either one would say no. Your heart's all screwed up because you're letting yourself be exposed to the jerk(s) you like and comparing it to your nice-guy boyfriend. What you need to be doing is building up your boyfriend, encouraging him, and... (read in full...)

B/f thinks if I have sex with another girl it will help our relationship

Q.   Hello DC aunts and uncles. I'm in need of advice, I will make this short. My boyfriend honestly believes that if I have sex with another girl it would "help" our relationship. Personally thats a load of bull. I know it won't I know things will only ...

A.   16 March 2011: Your boyfriend is full of it, and you've fallen in love with a prick (most likely *because* he's a prick). Unless he has a laundry list of redeeming qualities you haven't shared with us, I'd say leave him for a guy who can be satisfied with ... (read in full...)

Why are guys such pigs?

Q.   Why are guys such pigs? Ok, so I've recently started talking to a guy from high school. I've been out of high school for about four years, and it's nice to be able to reminisce with him. So we've been talking. And suddenly, he starts telling m...

A.   16 March 2011: It's not harassment, he's hitting on you. He's doing a crappy job of it, but still. Either tell him you're not interested and stop flirting, or you accept that you're signalling interest by flirting, laughing, and thanking him. You said you're f... (read in full...)

If he's got a girl, then why is he walking me to class?

Q.   Why would a guy walk around with a girl? Like from class to class? Are they friends, or is there something more there? If he is interested in her, would he take the time or make the effort to still say hi to me? What do you think?...

A.   16 March 2011: Depends. If he's the cheating type, he may be hedging his bets, seeing if he can set something up on the side. If he's not, maybe he just likes hanging out with you? Every single interaction a guy has with chicks doesn't have to be about se... (read in full...)

Love hurts! But why?

Q.   Many people believe that love is a sensation that generates when Mr. or Mrs. right appears.Many people approach a relationship either consciously or unconsciously, they believe love is a sensation based on physical and emotional attraction that ...

A.   16 March 2011: All those things you say "many people believe" are not quite what really happens. "Many people believe that love is a sensation that generates when Mr. or Mrs. right appears." Or Mr./Ms. Wrong. Some of the most desperately, deeply in-love p... (read in full...)

Marriage has gone from husband/wife to mother/father

Q.   I've been married for 7 years, and have two beautiful children who mean the absolute world to me. Since our first child was born, our relationship seemed to go from husband and wife to father and mother, with the entire emphasis of our relation...

A.   16 March 2011: First off, it's good to see you so devoted to your kids. Keep that close to your heart. Now, your wife is wrong in denying you sex. Exclusivity requires availability. And as you said, she is getting all her emotional needs met through your kid... (read in full...)

Would you rather be single, or with someone you don't know is lying to you about having cheated on you?

Q.   Is it better to be alone or in a relationship with someone who has betrayed you in the past by cheating, and who continues to lie about having been faithful and committed throughout the relationship? Is it true that what you don't know, can't really ...

A.   15 March 2011: In the strictly hypothetical sense... If you believe in subjective morality, then what you don't know really can't hurt you. You're happy, so everything is good. If you're a normal, well-adjusted person who believes in objective morality... (read in full...)

How do you play hard to get by text?

Q.   How do you play hard to get when texting a guy? I know most people don't like the idea of the 'play hard to get' game. So please, if you're one of them, this question isn't for you. ...

A.   14 March 2011: Don't do it by text. Ever. "Hard to get" works by using words and actions to seem disinterested, while conveying with body language and facial expressions that you actually *are* interested. This is what drives guys to chase you - and by chasi... (read in full...)

How to break up with a manipulative smooth talker bf

Q.   Dear Cupid My bf of 2 years often never calls for a week/two and then suddenly pops up again in my life. Whenever i question him, he says he was busy with work or other stuff. Never communicates anything to me before he disappers. I ...

A.   13 March 2011: Block his calls, delete your contact info with him. Change your number if it's really necessary. However, if you must talk to him to get him to stop, here's a little fable. Socrates, famous for his persuasive skill, was imprisoned and about to... (read in full...)

Why am I a bad person because I use prostitutes?

Q.   Dear All, I am going to ask few questions which might offend some of you if they do please pardon me and try understanding my query. I have few basic questions about life which I want you to answer but before that let me give you some insight abo...

A.   13 March 2011: "If I tell you that not even a single girl... has ever considered me worth while giving me a second glance let alone dating does it sound odd." Nope. Sounds normal. You have acquired all the traditional markers of a good, decent, and honorabl... (read in full...)

Males: What's your ideal woman look like?

Q.   Hello everyone, Do men prefer a clever, curvy, brunette or a skinny, clever, blonde? Males veiw . . . Thanks everyone...

A.   13 March 2011: A lot of things are tough to generalize. There is some data on a few things, mostly done by evolutionary psychologists, but some of it is disputed - for instance, lighter hair tends to indicate youth, which tends to indicate fertility, so blonde ... (read in full...)

Justified in my divorce request?

Q.   I have been with my husband for a little over 4 years, married almost 3 years now. When we are alone together, everything is great. We enjoy each other's company and can chat for hours. However, I know he fits only into one aspect of my life -- he ...

A.   12 March 2011: Your husband is right - this is a terrible, shallow reason to leave. You have every right to expect him to change, of course, but you have to work with him and realize this is not something that everyone can just "leave unsaid." Talk with him... (read in full...)

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