Miss Information: I'm overweight, shy, and insecure. How can I lose my virginity?

Miss Information

Have a question? Email . Letters may be edited for length, content, and clarity.

Dear Miss Information,

Breaking up is difficult, especially when you were never a couple. We met at school. We were both twenty-one and single. I started falling in love with her, and then she started dating a thirty-three-year old. I told her about my feelings and she was amazing about it, even though she said she wasn't sexually attracted to me and couldn't see us as a couple.

We had amazing dates and loved holding hands and being arm-in-arm. It might not have been right, but I enjoyed every single moment. Her boyfriend rarely did anything with her, so I may have simply been filling a void.

I eventually found out that she was going to break up with him because he wanted to have sex and she didn't. At first I was relieved and excited, but I quickly became scared and started imagining the worst. She's slender. He's a former weightlifter. She wants to break up. He doesn't. She's alone at his place. Arguments escalating to violence. She winds up hurt. And so on.

I tried calling her cell the day she was going to break up with him but couldn't reach her, so I called her house, and her older brother picked up. They don't get along very well, so he only knew that she'd left work and nothing about what she had planned for later. He invited me out for coffee and took a liking to me, which made me want to be with her even more. He felt his sister was being used and that the boyfriend was no good, and that it was time for him to step in. Awesome!

Not awesome. I received a call after getting home. She found out what I told her brother and was angry, which I understood since what she told me was private. However, I put her safety over any sort of intimate relationship I'd been longing for.

I've tried calling her a few times since and even bought her flowers but no luck. It's been two months and her birthday is coming up. I plan to call her to wish her a happy birthday but I'm not sure what that would mean. I do, however, know that the call will be the extent of it.

I'm still wondering though if I should have said anything to her brother, if I did good by putting her well-being above my desires, and if I should wish her a happy birthday. — Alive and Well

Dear Alive and Well,

There's a thin line between concerned friend and stalker-in-training. Perhaps "stalker" is a harsh word. Why don't we go with "unintentionally selfish and overbearing?" It's the only phrase I can think of to describe a lovesick schlemiel who goes out for lattes with his non-girlfriend's estranged brother, shares secrets that weren't meant to be shared, and leverages a fantasy about dating violence to position himself as the Superman to his crush's Lois.

You do want to be Superman, Alive and Well, however much you may be in denial. The history between you two may be twisted, but it's very clear that you adore this woman — so much so that you're willing to look beyond all the negatives. (Like her not liking you. Aaaaaand her already having a boyfriend.)

You've managed to convince yourself that you're being some kind of altruistic super friend, but it's my duty as an advice-giver to tell you that you're not. The day-of-the-breakup worrying, the meeting with the brother, the birthday call — all of those are attempts to deepen your relationship with her. You say you'll ring her up, say happy b-day, then leave it alone. I don't think so. Because I've been there. We've all been there. You want her to interpret it as a touching gesture, a welcome relief from the searing loneliness of having all her friends ditch her on her special day. Maybe she'll ask if you're free that evening. Maybe you'll wind up having coffee and pie with a candle in it at a cozy little diner. Then, she'll lock herself out and have to spend the night at your place. Without pajamas.

Not going to happen, Alive and Well. Vigilance and (arguably) good deeds alone will not make someone love you. Moreover, if you genuinely believed her safety was in question during this breakup business, offering her an escort to his house and/or giving a vague heads-up to a neutral friend should have been the start and end of it. The rest is up to her. As far as the phone call, do the best thing for her well-being (and yours) and drop it. She knows how where you are if she wants to find you.

Dear Miss Information,

I'm a twenty-year-old straight male virgin with very little experience with women. Actually, make that no experience. Generally, I've either been rejected or haven't even taken the chance. I have always had pretty crappy self-esteem. I'm not that attractive, not very tall, pretty overweight, and slowly becoming more introverted and insular.

Whenever I talk to people about my lack of a sex life, I get told, essentially, "Just wait. It will happen," and, "You don't need to rush it." I feel that these are some of the biggest lies ever told. Maybe I'm being a little paranoid. I know there isn't some conspiracy to make me stay a virgin forever. But I don't think my friends really "get" my anxiety about sex and sexual relationships; beyond the physical pleasure, it's important to me to have someone value my body and share hers, and make a connection.

Am I wrong in that belief, especially since I have never been close to the real experience? If that's the case, would changing my outlook really transform me and help me meet women? Should I be annoyed with my friends, or are they speaking some truth? — Right or Wrong

Dear Right or Wrong,

Your friends are right and wrong. (Don't worry, this gets more helpful.) They're right in the way that inspirational photo plaques in your nana's bathroom are right. "Good things come to those who wait." (Imagine a hungry tomcat peering into a fishbowl.)

They're wrong in the sense that there are some steps you can take to help your virgin era come to a close. You need to create a social life and emotional foundation that are conducive to losing your virginity. Getting out of the house more often will help, as will cultivating relationships with female friends and getting in the habit of talking to strangers (especially female strangers), even if it's something as stupid as asking for directions you don't need. The journey of a thousand penises starts with a single smile. Other steps include taking better care of yourself and losing weight if you need to, as well as visiting a shrink and signing up for an online dating site.

I know what you're thinking with that last one. Oh sweet Christ, the rejection. Yes, there will be rejection. But guess what? It's happened to every single non-virgin out there. I don't care if you've already tried a few and failed. Try again. You want to join the club? You gotta pay the price.

You ask if you're wrong in the belief that sex is about connection and the meaningful sharing of bodies. I'd say you're right. Sometimes. Other times it's a drug, an escape, an experiment, a psychological weapon, or simply mindless fun. When your friends take a blasé attitude towards your concerns, this is them trying to tell you that your first-time expectations may be a little unrealistic. It takes multiple partners and perspective to come to this realization, and I don't blame you for not being there. I wouldn't be either. What you need to do right now is realize that you have value, my good sir, whether or not you've found someone to value your body through the act of intercourse.

Readers, any other recommendations for Right or Wrong? Are there any special tricks to succeeding at online dating if you're lacking in the looks and experience departments?

Comments ( 32 )

Dude #1 is a creep. Dude #2 needs a professional. A few years back one of my friends was post divorce from the only woman he'd ever had sex with. He was convinced he'd never have sex again and this attitude prevented him from getting laid. Rome Girl and I staged an intervention and got his ass to a high end brothel in Barcelona where we got him well and truly laid. Two weeks later he got himself laid by a non professional who became his girlfriend for the next year - and was able to do this because simply getting sex at all, even if it was paid for, upped his confidence and made him feel and appear far less desperate.

bart commented on Jul 19 10 at 1:20 am

Holy sh!t, is that Bart from the Blog-A-Log?

@Bart commented on Jul 19 10 at 3:07 am

I will say that, having been in one long term relationship, and it being your only sexual experience is pretty daunting as well. (perhaps not as much as the first time, but still.) I got lucky enough to find a great girl and enough alcohol to get over the second hump, but even if you have to pay for it: you do what it takes. Gratz to Bart for taking the bull by the horns for the friend.

Ryan commented on Jul 19 10 at 3:39 am

RoR, I feel your pain. Here's the thing with low self-esteem: girls can smell it. Trust me, I used to stink of it, and I didn't sleep with a girl till I was 24. Contrary to what we like to believe, girls don't gravitate toward tortured souls like us unless we look like the sparkle vampire guy, in which case we wouldn't be outcasts. My advice to you is to think about what you really want here. If you just want to stick your dick in something, that's easy. Save your benjamins and hire a pro (you want to really splurge here, or risk taking home a lasting souvenir). If you want a girl to hang around you all day and tell you how wonderful you are, hang out with your mom. If what you want is a mutually loving relationship with a girl you respect, start respecting yourself. That was the hardest lesson and the most helpful when I was really down on myself. You have to turn yourself into someone you like before anybody else will like you, and then it becomes less important for other people to like you because you like yourself. You win no matter what. Two hints: 1) learn to cook from scratch. It's great, it will score points with quality ladies, and I guarantee you'll drop pounds if you eat stuff you make yourself instead of processed crap. 2) Join a yoga class. I hated it at first and I do NOT recommend hitting on anybody there until you know them really well, but it does magical things to you. My girlfriend wishes me to add that she admires big guys who go to her classes because it shows that he's committed to changing his life no matter what other people think. She also suggests judo as a manlier exercise option. Godspeed!

mario commented on Jul 19 10 at 3:58 am

Hi Dude #2! For starters, you're only 20. When you're 25 onwards, then start seriously worrying. For the moment, don't pressure yourself, you're only young. Most people only lose their virginity earlier out of fear and social pressure, no matter what your friends tell you. You've got the most important thing down- sincerity. You can work out all you want but you can't fix assholism. Seconding Miss Information's advice about getting new clothes, seeing a shrink and working out. Clothes and workouts and physical wellbeing, at the very least, will make you feel better and look better and be more confident. Jogging/gyms are also a way to meet people sometimes :) Martial arts is dorky but you'll make friends, of both genders, and is more interesting than just a treadmill- try karate. You don't need to be a bitter alpha male; it's true that those guys are sexy and get laid more, but we don't actually *like* them. Get out there, be true to yourself, fail a couple of times and learn from it. The failure is important, because it'll happen- it happens to everyone. You just need to learn from it instead of letting it get you down. For online dating, I recommend OkCupid- high proportion of girls, for a dating site, fun algorithms. Just don't start messages with "I'm really good at oral sex" (I get that a lot) or be overbearing and you'll be fine :) There is no shame in online dating, ok? You're just widening your net. Hooksexup personals seem good too but I haven't used them. Good luck man ;_; write back in 6 months and update us!

Caitlin commented on Jul 19 10 at 4:30 am

Yep, it's me from the blog-a-log.

bart commented on Jul 19 10 at 5:40 am

Seriously dude 2, ignore some of the advice above, you really don't want to lose your virginity to a prostitute. For all sorts of reasons including how cheap it is likely to make you feel, but most importantly because visiting prostitutes is the sort of thing that only assholes do. Right now, your unlucky and initially unsuccessful with dating. It's a bummer, but doesn't compromise you. Becoming an asshole on the other hand, does compromise you. Don't do it.

alex commented on Jul 19 10 at 7:22 am

@#2, don't outsource to a pro. Sex is kinda like driving a car, in that the first time you do it it's special and Hooksexup-wracking and needs to be done with someone who understands how important it is to you (but not done with your mom - that's where the similarities end). Six months after starting, it's still fun and worthwile and definitely important, but all the pressure's off and you can start having *fun* with it. Outsourcing sex is fine once it's an activity, not a huge psychological barrier. The biggest thing you can do is feel better about yourself. As a formerly-300+-lb-fatguy who lost it at 28 (the horrors!) now in good shape and happily married, I know exactly where you're coming from. Go learn something new, and get good at it. Doesn't matter what it is. Learn to cook, that's an awesome one. Learn to cook decent food (you don't have to be one of those raw-vegan weirdos, but don't make pastries for a hobby if you can't see your toes without a mirror) and you'll feel in command of something. Get some exercise, but do it in a way that puts you in touch with a community. Judo is good, aikido is good, hiking (with a club) is good, crossfit is f'ng awesome, and there are others. Don't go to those places hoping to meet women; you give off this "hey, I'm just here For The Ladies" vibe and you might as well get 'creep' tattooed on your forehead. Life really is one of those things where, once you stop worring about it, it takes care of itself.

eric commented on Jul 19 10 at 8:05 am

To #2, I lost my virginity at 22 for different reasons. But, the longer I waited, the more pressure I put on myself and the bigger of a deal it became to me and my friends. I had intimacy issues before and thought having sex would make them better. It didn't and I still have them. The sex was anti-climatic in more ways than one and having it won't solve your other problems. Find the route of the weight issues, the shyness, etc. and the rest will fall into place.

zerocaloriesweetener commented on Jul 19 10 at 11:04 am

for guy #1: https://forums.xkcd.com/viewtopic.php?f=7&t=31442 only you're being worse. yikes.

mp commented on Jul 19 10 at 11:17 am

This advice actually works for both guys: The biggest problem some guys have in dating is that they try and connect and connect and connect. Be your own person. State your own opinions, agree to disagree, walk away from rude people, cut your losses with women who don't want to date you. No person is worth selling out your self-respect. Guy #1, have some standards. Wow, she let you down easy? What a saint. Now thank her for that, and go find someone who actually wants to be with you. For both of you, it's not just about being good enough for HER. A woman has to be right for you as well. It's hard when you're still a virgin, but thinking about your requirements for a partner, and making sure potential lovers meet your standards will help your self-esteem, and avoid having that "desperate vibe."

Hooksexupsystem commented on Jul 19 10 at 2:13 pm

Guy #2, I felt your pain for a lot more years than you so far have and I know it isn't fun. I'd had setup dates, but never more than once, and never had a single success asking a woman out on my own. But keep your ears open for unexpected opportunities. A women I'd know casually for years who had been married got divorced. The idea of asking her out had never crossed my mind. She made it known to me, nearly too subtly since I wasn't used to that kind of thing, that I should. Turns out she'd been giving me signs for 3 months that I hadn't ever picked up on. After 3 dates, a bunch of text messages and phone calls, and one truly embarrassing round of herb infused over the clothes fumblings, she deduced my secret. She bluntly asked about it and I abandoned my plan to lie if such a question arose and told the truth. A few days later, she helped take care of my little problem. We're no longer together but I have wonderful memories now and I'm so glad I never saw a pro. I'm also now much more open to speaking with women, fell into a new social group because I could now keep up with some of their stories, and see opportunities around me that I would have never seen before. Chin up. And make friends with your hairdresser.. hint.

notme commented on Jul 19 10 at 3:46 pm

ROR -- Erin's advice is dead on. My boyfriend, who I've been with for 8 months or so, is 31 years old. He'd never really dated before me. He'd definitely never had a girlfriend or had sex. I'm 28, and while I've dated tons, this is the longest relationship I've ever had. I don't know if he's "the one" or anything like that, but we're happy now, we have a lot of fun together, and things are great. My boyfriend only ever started an online dating profile because his friends bullied him into it. I was the first person to message him. We've been together ever since. Things will happen when they're going to happen, but take Erin's advice about building a social life and your confidence. Join a club for a hobby you have and love or a skill you'd like to learn. I go to some photography group meetings and I take dance lessons. Neither ever got me laid, but I am a much better photographer, I'm now on a dance team, and I've met some fascinating people. And, to hell with being insecure about your weight. I'm most definitely fat. I have been my whole life. I let it hold me back all through college, but fuck that. It doesn't make me a less valuable person, or less deserving of happiness. It may make me less attractive to some people, but so does having brown hair, and I'm not going to get worked into a lather about that, either.

CAK commented on Jul 19 10 at 8:28 pm

Wow, I can't even wrap my brain around the creepiness of letter number 1.

S.S. commented on Jul 19 10 at 8:58 pm

Hint for dude #1-if a woman says she isn't sexually attracted to you-and she cant see the two of you as a couple-you are not on a "DATE."

jp commented on Jul 19 10 at 9:10 pm

"Getting out of the house more often will help, as will cultivating relationships with female friends and getting in the habit of talking to strangers (especially female strangers), even if it's something as stupid as asking for directions you don't need. The journey of a thousand penises starts with a single smile. Other steps include... visiting a shrink and signing up for an online dating site." Yeah, that's the advice I took a quarter century ago. Now I'm a 48 year old virgin with no women, no friends and loads of debt from dating services, therapists and anything else I could spend time and money on in hopes of expanding my social experience. Sadly, all that happens is that you train yourself to make small talk with total strangers. Which, unless the women are attracted to you already, does nothing to make them want to actually go out with you. If you're not comfortable with approaching strangers, you should probably learn how (acting lessons wouldn't be a bad idea) but it's not gonna get you over that hurdle between women being friendly to you and women actually agreeing to date you.

93 commented on Jul 19 10 at 9:24 pm

Hey #2, the best thing you can do for yourself is be able to like yourself. Women pick up on low self-esteem and desperation very easily. Also, I've noticed people I've dated tended to project their own attitudes onto other people, so if you don't like yourself, it might translate into a negative attitude toward your partner, and vice versa. I've also noticed that some guys who haven't had sex/in awhile get bitter and frustrated about it and end up intimidating their partners. Don't do that. ;) Also, never, ever complain to a potential sex partner about your lack of sex life. One guy I was briefly involved with did that, and it sounded like he was more obsessed with getting sex than he was interested in getting to know me. So...he didn't get sex OR me. The advice above about hobbies and social activities is sound. Also cultivate respectful relationships with the women around you and use respectful language around women in general. Good luck :)

Marie commented on Jul 20 10 at 12:59 am

Right or Wrong. Dude, you have nothing to worry about. I got out of my introvert through meeting ppl online, and being introduced to women by my friends. I waited till I was 27 to lose my virginity...yea....27. To me, it wasn't a big deal. When it comes it comes. But if u don't feel confident about yourself, then make the change now to change the way you look. Start exercising. Once you gradually go down in weight and have a better body, that'll build your self esteem up. It built mines up big time, and I wasn't all too afraid to approach a female. Make the physical change, first. It makes a big difference.

England commented on Jul 20 10 at 1:45 am

#2: I wonder if your bad luck with women means you're focused on pursuing conventionally attractive types. Or maybe you're only interested in women who you perceive as "super-hot" and out of your league, which makes you act self-conscious and awkward. So: strange question, but would you consider dating someone fat? That is, 50 lbs. overweight or more? There are lots of smart, sexy women out there who get ruled out by most men because of their weight, and know what it's like to feel "on the outside looking in" because of that. Some end up exploring alternative sexualities, and are enthusiastic about FWB and other non-commitment-centric arrangements. If you aren't a total creep, and are considerate and upfront and YOURSELF, you might find someone who digs the idea of "showing you the ropes" and sympathizes with your situation. Having it be casual-ish might alleviate your anxiety. (And maybe it'll even grow into something more. Sometimes serious relationships grow from casual flings where the guy starts out somewhat fat-phobic, but changes his mind after loads of great, adventurous sex.)

LC commented on Jul 20 10 at 2:10 am

Guy #1: just because her boyfriend's a big dude and he's getting dumped by a smaller lady doesn't indicate that he will definitely physically abuse her. If you're worried that a friend is in an abusive relationship, there are more useful ways of helping--like talking to her about her relationship instead of pretending that it doesn't exist until you want it to end--and none of which include following her around like a sad puppy. A person has every right to be livid with you if you go and air their dirty laundry for them to people that have absolutely no business knowing about it. Calling her on her birthday is just creepy and sad. You'd do well to leave her alone, because to her, you're not a knight in shining armor, you're the creep who couldn't mind his own business.

claire commented on Jul 20 10 at 8:48 am

Lots of good advice for guy #2 above, except for the prostitutes. (If you know she's just in it for the paycheck, and you think that's the only way you can get laid, it really screws up your outlook.) Here's something else. Try saying things that make people smile. Will that get you a girlfriend? Maybe, maybe not. (There's a lot of disagreement on that front.) What it will do is make you more comfortable interacting with people, and you need to get that down before you start pursuing romance. There WILL be times when you screw up and unintentionally hurt someone, like guy #1 up there, so be ready to apologize profusely when that happens, and don't let it discourage you. Don't lose weight just to make yourself "more attractive." There are plenty of fat guys with girlfriends out there, and if that's your motivation, you'll quit trying when you find one of your own. Instead, lose weight because it makes you feel better and feel better about yourself. Good luck!

JCF commented on Jul 20 10 at 8:56 am

LC: are you seriously suggesting that only the most attractive women exercise the option to reject men? Don't kid yourself; women of all shapes, sizes and ages reject or accept potential partners for all kinds of reasons, and just assuming that your odds will improve if you "lower your standards" only insults them and demoralizes yourself. Read his letter again. He's not overburdened with an excess of self-esteem so much that he's only hitting on the most conventionally attractive women he can find. And suggesting that it's his own fault for being too overconfident is only going to exacerbate his frustration. Fat women have the right to choose who they go out with just as much as anyone else, and being rejected by fat women doesn't feel any better than being rejected by anyone else. It's all just more pain.

93 commented on Jul 20 10 at 10:53 am

93, I obviously don't know you and don't know why you have had no luck with women in your 48 years, and why Miss Info's advice did not work for you, as I think it does for most people, but I am impressed that even with the amount of rejection you've experienced, you haven't just given in to hating women as many men in your situation have (remember the health club shooter?) Don't lose that. I wish the best for you.

LM commented on Jul 20 10 at 2:30 pm

Regarding Dude #2: Regarding the "professional" help: @Bart 2 and @93 are right. Those who preach against "professional" help obviously haven't gone that route, because they don't know what they're talking about. If I had not made that move to "break" my virginity at 21, I might still be a virgin today at 41. It DOES give give you confidence because a) you know what to expect, and b) unlike what JCF says, you don't "think that's the only way you can get laid," you just realize its an "option" for sex. This makes you act less desperate with real-life girls and value them more for them. You know there's no reason to settle for someone you don't really care for just because she will have sex with you, because know you can get that if you're willing to pay the dough (I do, however, advise going to Nevada for this, where it is legal and regulated). It's not true that only "assholes" visit prostitutes; in my observation, "assholes" don't need any help getting laid. I've tried nearly all the suggestions people have posted on this board. Online dating = don't write it off, but for a guy it's like playing the lottery. Yoga = tried it for the exercise, met a lot of married women who probably thought I was gay. Gym = I recommend; not for meeting people, but it'll make you feel a lot better about how you look. My advice: girls like "bad boys" and guys who can make them laugh; if you can't be the former, work on the latter.

Gar commented on Jul 20 10 at 3:47 pm

Oh, and I would like to add something else. My experience has been very similar to that of @93; despite what I mentioned before, I still have terrible luck with women, but I will mention something that I have had some success with: Travel abroad. Go solo, or, at most, with only one friend. Don't do any packaged tours or cruises, just plan your trip yourself. You know how the foreign exchange student always got plenty of attention from American girls? Well now YOU'RE the foreign guy. YOU'RE the one with the accent (and it doesn't hurt that the rest of the world seems to think all Americans are rich, even when you protest otherwise). And you've also put yourself in a situation where, not only is it easy to find an excuse to talk to a girl, often it's a necessity: "How do I get to [X]?" "Can you recommend a good [restaurant/hotel/bar]?" "Do you speak English?" Your appearance matters less because you've got the "sexy" foreign accent. They will be amused by your attempts to master the language, but admire you for trying. If you meet someone you like and you can't close the deal, give her your e-mail address; if she likes you, she'll e-mail you - and maybe the next time will be the charm, or, if you're really lucky, next time she'll come to visit you. It has happened.

Gar commented on Jul 20 10 at 4:57 pm

93 would you care to share your story here? I'm not sure if you're an American or not, but it may not matter and you can ask the lady who runs the site.

Harold commented on Jul 20 10 at 8:03 pm

Dude #2. Take up drinking. That's got me laid more consistently than looks, charm or intelligence. Liquid courage for you, and panty remover for them. Have at it!

Felix commented on Jul 20 10 at 8:54 pm

Travel abroad. Now I think that's a truly good suggestion. It goes both ways though... as a girl abroad I got more attention from higher-quality men as well...

@Gar commented on Jul 21 10 at 10:55 am

@Gar, maybe you're having bad luck with women because you push them all into a tiny box and assume we all want assholes or "bad boys." How long will it take people to realize that different people have different preferences? really, just not that complicated. Assholes have trouble getting laid all the time. Check yourself.

TS commented on Jul 21 10 at 1:18 pm

@93: I'm glad that my comment gave you an opportunity to feel self-righteous, but I don't think it has anything to do with what I actually wrote. To spell it out: the more people you exclude from your dating pool, the worse your chances are of finding someone. That's just simple math. Many guys rule out fat women not because they find them unattractive per se, but because of the social stigma attached to dating them. Get over that stigma, tell it to go to hell, and suddenly the number of available women has doubled (or more). This has nothing to do with whether or not "fat women have the right to choose who they go out with" (of course they do), or "lowering your standards" (only if you think that dating overweight women = low standards). Nor does it have to do with "overconfidence": lots of guys with lousy self-esteem still aren't willing to give up their fantasy of ending up with a Marilyn Monroe/Drew Barrymore/whomever lookalike.

LC commented on Jul 21 10 at 1:41 pm

For some reason my comment was deleted. Oh well.

Harold commented on Jul 21 10 at 7:18 pm

the advice from the commenters was much more interesting and I thought often helpful, I hope #2 came back to read them, he sounds like a nice guy and I hope he got laid with an understanding woman and they became good friends if not a couple.

Ferberzz commented on Jul 22 10 at 12:01 am

Dear Miss Information,

Dear Alive and Well,

Dear Miss Information,

Dear Right or Wrong,

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