Date or wait?
June 10, 2013 8:13 AM   Subscribe

I'm a man in his mid-twenties. I've never been in a relationship. I've never even taken anyone out on a date. I want to rectify this, but I think my mental health and my living situation prevent me from doing so. Should I even try to date? If not, what should I do? Details inside.

I don't have many friends. None of them are close. No friends of mine have ever been very close. I never learned how to make and keep friendships when I was young. Likewise, I never learned how to form romantic relationships with women. No one has showed any interest in me. I've been too anxious to show interest in anyone else. I haven't had sex. I haven't kissed anyone.

I feel ashamed of this fact, so I do my best to hide it, though it must be obvious to any observant person. I've always been anxious around women, particularly those I'm attracted to.

Social interaction in general makes me anxious. I easily convince myself that I'm not really welcome. After an hour or so of conversation, I stop talking and withdraw from the group. I rarely think I have anything valuable to add.

For a long time, I thought I was basically unlikable. I still have trouble saying I have any good qualities. I've been depressed for a long time. I'm currently getting therapy for the anxiety and the depression.

I've lived at home since graduating college. I pay my parents a below-market but not inconsequential rent. Most of my income goes to my student-loan payments. My job isn't in the field I studied for, and I don't expect a promotion, a raise, or a change to a better job anytime soon. That said, the pay gives me a little room for recreation. I try to pay as much toward my loans as I can. If I wanted to, I could wipe out much of one of my loans, but I would need to wipe out much of my savings with it. I don't like the thought of not having any money for an emergency.

I'm going to be taking swimming lessons this month. I try to swim as much as I can. Unlike other kinds of exercise, it feels good, though my form is bad. I feel much less anxious after exercising. I hope to start a regular swim routine on the weekdays.

I'm inclined to think I should get my house in order before trying to date. I can't imagine a woman my age would want to date an unattractive, poor, sexually inexperienced wreck who lives with his mother. If she did, I doubt the relationship would last long, and if it did, it probably wouldn't be healthy.

At the same time, I should find some way to become less socially stunted, particularly at my age. I can't learn how these interactions work if I don't ever try them. I don't know whether it's possible to recover after such a long time, though.

Given all this, should I try to date? If so, how should I do it, and how should I handle not having a place of my own? If not, what should I do instead? What should be my attitude toward my inexperience?

You can reach me at
posted by anonymous to Human Relations (34 answers total) 9 users marked this as a favorite

Most dating relationships start as friendships. Work on getting some friends, then dating. This isn't as bleak of a situation as you think. There are plenty of nice women out there who don't have a lot of money or sexual experience and are possibly living with their parents while trying to pay down their student loans. In some ways, sexual inexperience is a good thing because it means that you don't have bad habits or think All Women Like This. So work on yourself, work on making some friends, and try to feel less badly about your situation. It's temporary and it'll get better with work so put some work into it.
posted by kat518 at 8:23 AM on June 10, 2013 [7 favorites]

Relationships with people go on a spectrum of intimacy like : aquaintences - friends - dates - close friends - partners. And it sounds like you want to jump right into the most challenging (but most rewarding) intimate relationship of a partnership. I think you need more practise at the other (lower stake) levels of friendship so you can learn how to be healthy in a relationship, assert boundaries, be compassionate and empathetic towards others. A volunteer position (with other people) using your skills is a great way to build up your relationship experience while also contributing positively to the community and meeting possible new friends.
posted by saucysault at 8:25 AM on June 10, 2013 [5 favorites]

I feel ashamed of this fact, so I do my best to hide it, though it must be obvious to any observant person.

I'm sincerely baffled by this. What discernible, observable trait do you think distinguishes people who have kissed or had intercourse from people who have not?

I can't imagine a woman my age would want to date an unattractive, poor, sexually inexperienced wreck who lives with his mother.

To paraphrase Shit My Dad Says: "Son, let women reject you themselves. Don't reject yourself for them." Plus, I think it will be helpful for you to understand that you -- in common with everyone else - can have like, 30 one-off coffee dates before you find someone with whom you share mutual attraction and have a second coffee date that can even vaguely be construed as "dating" because that's just... how it works.

If she did, I doubt the relationship would last long, and if it did, it probably wouldn't be healthy.

That's the depression talking. Ignore it until you get better and it goes away.

So you know, try online dating. Have 10 20 or 100 one-off coffee dates and you'll get really good at them. That seems like your biggest hurdle to me: putting yourself out there is a much bigger barrier to cross than learning to kiss.
posted by DarlingBri at 8:27 AM on June 10, 2013 [8 favorites]

You need to look at the things you've said about yourself as just facts that are part of who you are, not the most important things or even things that should drive the narrative of your life. Have you tried online dating? First, writing an engaging profile should help you figure out what things about yourself are laudable. Secondly, getting dates will help you get better at dating.

I never thought of myself as particularly desirable to girls, and I had to do a lot of reaching out to people online to get a small number of dates, but it will click at some point and you'll be going on dates. A little confidence can go a long way.
posted by moviehawk at 8:30 AM on June 10, 2013

You can recover. The secret is that everyone feels lost at this stuff sometimes, and even a ton of experience doesn't prevent you from sometimes feeling nervous. Every person has some things they feel anxious and insecure about, even the people who you think have it all together. So you're not starting at as much of a deficit as you think.

The only way to get better at interacting is to start doing it. I think you should try now. If you keep waiting for the perfect time, you'll never do it.

You can do it living with your parents. However, if you can swing moving out I would try to do so, just because it opens up your world and forces you to grow some. If you can't do it, that's okay.

Start doing things that make you feel good about yourself. If you frame everything in a negative way, it will be hard for even the most wonderful things to be seen as positive by your brain. It's okay to be realistic, but at some point realistic becomes negative. If you really think you're unlikeable, why? Are you intentionally mean to people, do you make them feel bad? If so, then you've got some stuff to work on. You probably aren't though. Not everyone will like you, and that maybe doesn't even really have to do with you, but that doesn't mean you're unlikeable.

Girls don't care that much about how experienced you are, btw. And they don't want to date someone more because he's been around the block. If you find someone you like and they like you, then you can figure out the experiences together.

Make some friends that you enjoy spending time with. On preview, good points about starting with friends and lower level intimacy. Walk before you run and all that. Just start, and keep at it even if you feel sometimes like it's not paying off.
posted by KAS at 8:34 AM on June 10, 2013 [1 favorite]

If you wait until you're an ideal dreamboat that no one in their right mind could ever possibly not want to date, then you'll be waiting for a very long time indeed. You need to work on yourself, sure, but a lot of what you see as a problem is not something that anyone else but you can see. There's no way that anyone can tell that you're a virgin just by looking at you. You'd have to tell them for them to be sure.

You absolutely have to start getting yourself out there. It is scary at first, sure. There will be rejection. But there will also be people who will enjoy your presence. People who will love seeing you around. They say that you miss 100% of the shots you don't start taking some. Get out there and start growing!
posted by inturnaround at 8:41 AM on June 10, 2013

Honestly, I'm not going to lie to you and tell you to reach for the stars like some other people will do, because I hate doing that kind of forced-urged-optimism "think positive andyour life will magically fix itself!" stuff, especially to people who are essentially rational and smart, and you do strike me as level-headed, rational and smart. Which, by the way, is a very nice quality. (I say this as a 25 year old female who works in a call center and barely supports myself, so close to your "target demographic")

So here is brutal, harsh-ass honesty for you: I would not date a virgin again. I've dated two, and I'm done. However, more women at about my situation in life would once or twice, more than you think. The main problem with virgins is that they are very clingy and needy as a general rule, and for someone like me, I can't afford to get pulled down with someone who has never handled te rush of positive and negative emotions that come with breakups and sex, etc. I know many people will hate this answer, but my honest advice to virgins is to just get it over with as soon as possible and don't expect your first to be a lasting relationship.

For the other stuff: Living with parents isn't so much a dealbreaker for itself, except that it makes it impossible to have sex. But tons of girls/women our age have roommates who may even be less accommodating of sex in a shared living situation, so that's not your biggest obstacle.

Underemployment is no biggie, it's practically the norm, as are student loans.

No friends is a bit worrisome, but can have Reasons. No friends without Reasons is kinda bad, mostly for aforementioned "clinginess."

Main thing is, I can't save anyone, I have enough problems.

Do get an okcupid account, and do try, but don't get discouraged, and try to just enjoy talking to people and the slow process of improving your life step by step, piece by piece. Do not hang all your hopes on a Perfect Relationship with an Understanding Girl.
posted by quincunx at 8:43 AM on June 10, 2013 [3 favorites]

Poor = lots of girls are poor as well, so you're relatable.
Living at home = lots of girls in your age and in these economic times live at home, so you're relatable.
Sexually inexperienced = many girls are in the opposite situation, meeting men that are way more experienced - you're relatable.

Unattractive = it's your self-loathing that's most unattractive and will drive the most likely of potentials away, no matter how rich, attractive, penthouse dweller you might be. Seek help for this part first, the rest will stand a much better chance.
posted by Kruger5 at 8:43 AM on June 10, 2013 [1 favorite]

Should you work on getting your house in order? Absolutely. Should you refuse any and all social interaction prior to that unidentified date in the future when Everything Is Fixed? Hellllll to the no. You have said you never learned to build or maintain friendships. Well, dating is basically a long friendship with sex, so, friendship is a thing you have to learn about.

So add it to your list of things that will constitute getting your house in order: learning how to be a friend and have a friend. Are you in therapy? If so, your therapist can be a great ally in helping you take the not-close friends you have, and turn them into closer friends. If not, I'm sure the MeFites can recommend a number of useful books!

Nobody can tell that you're a virgin. That's your depression and its intense self-focus talking. Literally the only thing anyone is going to know from looking at you is "well, that's a dude, probably." OK, maybe they can reasonably extrapolate, "that's a YOUNG dude."

I get the sense from your question though that you want our permission to continue not-dating, because you don't feel ready. In that case, you absolutely have my permission. But please, please do consider the making-friends project, even if you Don't feel ready--leaving your comfort zone is going to have to happen at some point, and there's no time like the present, and that's a relatively low-stakes way to start.
posted by like_a_friend at 8:45 AM on June 10, 2013 [1 favorite]

I can't imagine a woman my age would want to date an unattractive, poor, sexually inexperienced wreck who lives with his mother. If she did, I doubt the relationship would last long, and if it did, it probably wouldn't be healthy.

You cannot read women's minds. Therefoe you do not have any idea about who women will and will not date. Nor can you predict the future in regards to the length of the relationship and the health of that relationship. You do not know the answer to any of these questions you presume to answer. Ask yourself if you have no experience, how can you know the answers to those questions?
posted by Ironmouth at 8:47 AM on June 10, 2013 [1 favorite]

I would say: It's not that you shouldn't try dating, far from it, but that maybe your first priority shouldn't be dating. Make some decent friends, first. Having no real outside friends is far more unhealthy from a relationship perspective than anything else you mentioned, and having real outside friends will make getting your life in order easier, give you some support in meeting people, possibly even lead to meeting somebody, who knows.
posted by Sequence at 8:53 AM on June 10, 2013 [1 favorite]

Work on making closer friends with people first, then try dating. Dating can be an extension of friendship. You can do both of these while living with your parents; you're not alone in this situation.

Find some meetups. Meet people. Cut down on the negative self-talk, on telling yourself people don't want to talk to you.
posted by RainyJay at 8:59 AM on June 10, 2013

There's lots of great advice here. I know a guy who has struggled with some of the same issues including the virginity and feeling unattractive. He's met the love of his life now, not through any deliberate searching, but by gradually putting himself out there and developing the confidence to be himself and talk to people in social settings. Basically, he was just being his awesome self and happened to make a new friend and it blossomed into something more. I can assure you that the woman in question does not think of him as poor, unattractive, or any of those things.

Speaking for myself, a woman with different but related issues (social anxiety, feeling unattractive), getting out there socially is the one thing I have done for myself that has improved my self esteem the most. For me it was a hobby group that broke me out of the prison I had built for myself. Once I had grown comfortable being around people again, only then was I ready to meet the guy I love now.

The thing is, I know everyone gives that advice, and I waved it off for years because I was sure it was a pile of shit. But then hey, I was going out weekly to meet up with my knitting friends, and I could recognize that it really did make a huge difference and made me want to make other changes in my life too.
posted by cabingirl at 9:02 AM on June 10, 2013 [2 favorites]

Date! Absolutely do not wait.

From your intro, I was expecting something really bad below the fold. But you're doing fine! You're employed, you've got a roof over your head, you're not in trouble with the law or suffering from a major personality disorder or paying maintenance on 5 kids. So you're a virgin, big whoop. Trust me, nobody can tell just by looking at you.

I'm deliberately being a bit flippant here to emphasize that you're okay. You really are. Your biggest obstacle to getting out there and meeting women is not recognizing that.
posted by Salamander at 9:02 AM on June 10, 2013 [1 favorite]

You really don't seem to understand that the vast majority of women are kind, caring, empathetic, and really just want to be in a healthy and happy relationship with a kind, caring, and empathetic man. Not a rich guy, but a really, really good guy who tries to improve himself every day to be a good boyfriend or good husband and a good person to his neighbors and community.
posted by discopolo at 9:07 AM on June 10, 2013 [11 favorites]

I can't imagine a woman my age would want to date an unattractive, poor, sexually inexperienced wreck who lives with his mother. If she did, I doubt the relationship would last long, and if it did, it probably wouldn't be healthy.

This is a self-fulfilling prophecy simply because how much genuine respect would you have for a woman who chooses to date a dude who you think is unattractive, poor, etc.? A relationship that isn't founded on mutual respect is inherently going to be short-lived, unhealthy or both.

Make self-esteem a big priority in your therapy sessions. Work on seeing yourself for a real human being, and not a Frankenstein's monster of perceived failings. Once you start valuing yourself, your idea of dating won't be nearly as catastrophic, and that will help with the anxiety.
posted by A god with hooves, a god with horns at 9:08 AM on June 10, 2013 [2 favorites]

But you really have to learn to genuinely like yourself and other people before attempting to have a relationship. Also, you have to be giving in a relationship, and not focused on using it to lessen your loneliness, feeding your ego, or just getting sex.
posted by discopolo at 9:11 AM on June 10, 2013 [2 favorites]

I lived at home at your age and dated! Lots of women are in the same boat as you. I agree with other posters that you should focus on making friends first. When I was in my mid-20s, the only red flag I would have seen with you is your lack of friends.
posted by parakeetdog at 9:12 AM on June 10, 2013

Women are more understanding than you imagine. I think many women your age would understand crushing student loan debt and would understand living at home to try and pay some of it off. After all many of them are also struggling to pay off debt. You sound like you have very low self esteem and therapy would do you a world of good. I dated a couple of guys on my twenties who lived at home. They came to my place. It was a big deal.
I think you should try and date. You are looking for someone to love you as you are(not some idealized version of you)
posted by bananafish at 9:15 AM on June 10, 2013

I think it's important to make friends. Having other relationships that you value is a key to making a romantic relationship work: you can't hang all of your hopes and dreams for happiness and human interaction on one woman. People who do have friends still make that mistake all the time, and therapists would usually call it codependence. Make friends first and see how they can enrich your life even though you don't have sex with them. Then start to dip your toe in the dating waters.

And I must echo advice above re: coffee dates set up online. You can easily go on TONS of them without ever encountering a spark. I've had plenty of relationships, kissed, had sex, been asked out, asked out (and received a yes), and so on and so forth, but in my entire online dating career never got so much as a good night kiss or a second date. It's a numbers game and it's also just awkward for certain kinds of people. So please don't be discouraged if you start trying OkCupid and it doesn't work for you. There are LOTS of other ways to meet women, but don't worry about that just yet.
posted by telegraph at 9:30 AM on June 10, 2013

Ask your therapist to coach you on developing relationships, with friends and with women. It takes some practice to learn how to make friends, and your therapist can help you deal with the fact that a lot of people have a full slate of friends, or don't click with you, etc., and hang in there until you make some friends and date some women.

Get a 2nd job, mow lawns, whatever, and take a Dale Carnegie course. A lot of people have gotten a lot of benefit from it, and it's a safe environment to learn people skills. Get books from the library on how to talk to people. It's a learn-able skill.

You have a job, savings, and a plan to deal with your finances. Plenty of people don't have jobs, have lots of consumer debt, don't have a plan. You're doing fine. Here's a fact: you see the surface of other people, and they seem to be doing fine. But you'd be amazed to find that many people have the same interior fears that you have, or are a financial mess, or are dishonest or mean, or are scared to death. You're dealing with your fears, you're getting in shape - way to go!

Start taking classes - Adult Ed., pottery, whatever. Go to lectures and events at the library, museum, art galleries, etc. Let people talk to you, and learn to talk to people. To be interesting, it helps to have interests, and you need to get out of the house. Even if it's just going to a coffee shop every Tuesday after work, and a bookstore every Weds. after work. You can start to chat just a little with the now-familiar clerk. It's not friendship, but it's practice.
posted by theora55 at 9:39 AM on June 10, 2013

I was in your shoes not long ago---much less experienced than I should have been for my age, really insecure about it, sure I would be alone forever etc. And I wound up meeting a lovely guy who had some personal issues which were ongoing but being healthfully dealt with, and who confessed to me on the second date that he was shy about sex and not that experienced because he had surgery as a child and has some scars from it. I can't tell you what a relief that was! And it was so ironic because this was his big thing that he was insecure about, and it actually was a selling point for me. I felt like he would not judge me for my physical issue because he knew what that felt like. I came clean to him about my history in this area and he was slow and gentle with getting me comfortable. Two years later, we are still together, the stuff he was working on has for the most part cleared up, our intimacy stuff has no problems and we are happy as can be.

My point is, the relatinship won't be just about you. You have no idea what sort of background the girl will have and what her needs will be. Maybe she'll feel like because you worked so hard to get her, you'll appreciate her more. Maybe she is happy to meet someone who has no expectations or past experience to compare her to. Maybe she shares an interest with you that she'd love to talk about. You never know!
posted by JoannaC at 9:44 AM on June 10, 2013 [2 favorites]

See if your therapist can recommend a therapy *group* for you. This can serve as a transition from social awkwardness and isolation to getting experience in relating to others and eventually forming close relationships.

I am not your therapist and do not function as one on the internet. Just friendly advice that also happened to work for me personally.
posted by DMelanogaster at 9:52 AM on June 10, 2013 [1 favorite]

I don't think you should decide not to date yet because of any of your reservations about dating.

As others have touched on, dating is very unlikely to happen unless you start interacting with people. Clubs, churches, causes, volunteering, classes, work, support groups could all be the place. I suppose bars could be thrown in as well but some bars have a dynamic of insiders/regulars testing, initiating, or rejecting newcomers which would likely be hard someone socially inexperienced.

I'll suggest toastmasters. I've not been but a few of my most introverted friends who have been counted it as vital in their achieving their social confidence.

Eye contact. If you have problems making eye contact, its going to be a priority to accustom yourself to being OK with it. People who don't make eye contact seem to be telling people they want to be left alone. No eye contact can also be unnerving to some people.

If social anxiety has been a part of your not interacting with people there are many approaches that could lessen your social anxiety.Besides easing into social situations you could try therapy or medications.

There will be some blunders. Everybody makes social blunders. The only way to avoid social blunders is to never socialize. Don't blow things out of proportion. Don't be black and white about things. It is not that people are either likable or unlikable, socially competent or socially incompetent. Everyone is a mixture of traits. The most beloved of people have people who really don't like them. Traits that one person finds charismatic other people find annoying.

You will be fine.
posted by logonym at 10:02 AM on June 10, 2013 [1 favorite]

Nobody wants the person who doesn't want themselves. None of the circumstances you describe will make you unattractive to women, it is your attitude alone that is the problem.
posted by mani at 10:08 AM on June 10, 2013 [2 favorites]

I am something of a future version of you. I hadn't dated anyone until I was in my 20s, and my group of friends was always pretty small, and mostly formed thanks to my more out-going friends who made connections to people, and I just joined in. I was awkward around women I liked. I was over-thinking everything, imagining that if I dated anyone, I would most likely ruin whatever friendship we had, so friends was good enough.

I was lucky that my first girlfriend was more assertive than I was, and asked me out. That broke the ice for me, and I tried (and succeeded) in asking other women out, once I realized that I should just try and learn from my efforts.

Now I'm happily married and we have a kid, but I'm still socially awkward. I need to push myself to talk to people, and it helps if I just go and talk to people, before I get the chance to think about all the ways I could mess up my introduction or come across as a weirdo. Practice, practice, practice.

If you're uncomfortable with presenting yourself to people, you could join Toastmasters or some other group that helps people present themselves to others. I've thought of joining for a while, but haven't made the time to do so.

The main problem with virgins is that they are very clingy and needy as a general rule

I think this isn't so much about virgins, as it is that inexperienced daters can be clingy. I was at first, but I don't attribute that to being a virgin. Being with someone who liked me was a rush, and I didn't want to spend much time away from her. But again, experience helped there.

You'll have some awkward experiences and non-great dates, and maybe some relationships will sour. But there will also be great experiences, splendid dates, and fantastic relationships. Focus on the good that could happen whenever you think of all the ways something could go wrong. Or just plunge in and introduce yourself, all the while thinking upbeat thoughts. Living with your mother, being poor, and being inexperienced haven't stopped other people from being in happy relationships. To paraphrase sh*t my dad says, let women figure out why they won't date you. Don't do it for them. And another suitable aphorism is "the perfect is the enemy of good" -- don't wait for the perfect moment to act, go ahead and put yourself out there when you're feeling good. There is no perfect moment, but plenty of good times to introduce yourself and make friends or get a date.
posted by filthy light thief at 10:09 AM on June 10, 2013 [1 favorite]

Dating kinda sucks, be warned.

It's uncomfortable and awkward when it's happening, and it leads to feeling rejected or else rejecting someone else, both of which are unpleasant. Not always, but often.

It's nothing special about you if you have a sucky date. It's normal. It's impossible to not take it a little personally, but don't take it too personally. Some unpleasant dates--maybe a lot of them--are part of the ticket price to get in the door.

In general, you're not going to improve much socially unless you do things a little outside your current comfort zone. You gotta fall down some learning to walk. Good luck and hang in there.
posted by mattu at 12:06 PM on June 10, 2013

Consider a couple of swimming lessons too. Better form means better enjoyment, better exercise for your muscles, and maybe the admiration of a female swimmer.
posted by Cranberry at 12:07 PM on June 10, 2013

In addition to the above I would like to give you some financial advice: get IBR for your loans. I know they will take longer to pay off and I know you'll end up paying more money in the end, but bear with me as I present you two scenarios:

1.) 10 years from now you're still in your current position. Your job offers no hope or possibility of advancement, you're still living with your parents, you're still doubting your self-worth. But now you're ten years older. And your debt is paid off. Whoop-tee-doo.

2.) 10 years from now you moved out of your parent's house, paying for an apartment with the money you saved on debt payments. Or you still lived with your parents but supported yourself through a job search. Or you kept the job but took night classes at a community college for accounting or programming or some employment-related skill. Or you took a fun class like improv or pottery (swimming is fantastic exercise but usually not very social) and met new people, maybe even a girl! At this point your debt is not paid off, but you have friends/skills/experiences that you wouldn't otherwise have, and besides, President Warren just passed a national student debt forgiveness measure so you're in the clear!

The point is that if you can make things happen now that will significantly improve the quality of your life then what the hell are you waiting for? You're in a bad place, and the sooner you can get out the better. This is your life. Your debt? That's just a number on a page.
posted by Ndwright at 1:09 PM on June 10, 2013 [4 favorites]

Pay no attention to some of the more cynical answers here unless you are looking to merely get laid. In fact, if that's all you're looking for, don't read any farther.

Ok... so if you're on this paragraph I will assume that's not all you're looking for.Getting your house in order is fine but don't let that stop you. Your future partner will work with you on that one.

Just remember this: it doesn't matter who you are, where you're from, what you look like, where you live, or how much you make... there's someone out there for you but if you continue to be your own worst enemy (as you appear to be) you will never meet this person. Get out there, talk to people, be friendly, cultivate a hobby... you will meet someone. Repeat as necessary.
posted by brownrd at 2:09 PM on June 10, 2013

Yes, you should absolutely start dating! I'm a 38 year old woman and for real I couldn't tell you if anyone I've ever met has/hasn't been a virgin. It's really not the scarlet letter you think it is. If you come across as quiet and shy, a woman may think "hey, this is a quiet and shy dude!", but I guarantee you they won't automatically extrapolate to "and he's never had sex and I must leve the room now!" As previous commenters have mentioned, quiet and shy and not a lot of experience can actually be a positive for a girl who is the same way.

I also seriously wouldn't worry about being talkative at the start of a night out with friends and quiet towards the end. NO ONE has ever said "man, that guy is a real asshole. He just won't stop being silent!" People probably really enjoy hanging out with you because you listen.

So here's what I'd recommend. Make a goal to go on 10 first dates through Internet dating. Like people above have mentioned, even if you have a robust sexual/dating history 90+% of your Internet dates will stay in first-date only territory. So during these 10 dates, don't stress out. Don't even wonder about whether there will be a second date. Your goal is 1-2 hours of conversation with 10 different women. You may send one follow up email afterward saying "thanks, I had a fun time!" If she asks YOU out, go on a second date. If she doesn't, don't worry about it. I guarantee you it is just the way most of these things go and has zero to say about you as a person. (You might wonder why I don't suggest you ask out the ones you're interested in. That's because I don't want you to get too caught up in the "everything depends on this!" mindset. Use these dates to figure out what makes you like some girls better than others. Then use that knowledge in your NEXT 10 dates to ask no more than 4 of those 10 on a second date.) This may all sound super silly/stilted to you, but the beauty of this is, there is no secret magic to it. Do all of this and you will be DATING. And once you're confident enough with that initial step that going on a date in and of itself doesn't worry you, then you should have a good idea of whether or not you like THIS girl, as opposed to just wanting A girl. And then, voila! You're in the same boat as the rest of us!
posted by MsMolly at 6:04 PM on June 10, 2013

There is nothing wrong with you except your attitude and once that changes, there is no reason at all why you shouldn't be really successful at dating! You're employed, you're well educated, you're financially responsible because you're paying off loans. You're getting healthy and you want to be in a loving relationship. Sounds pretty good to me. Lots of women will find that attractive.

The virgin thing, there are many, many women out there who would love to take you under their wing and teach you what works for them. If you're eager to learn and positive about it, you can have an awesome sex life in front of you. Much more appealing than a player who think they know it all. I would view it as "Your willing pupil" kind of thing instead of what focusing on what you don't know.

You just need to get out there. Focus on meeting people and forming basic friendships first, as everyone else has spoken about. If you try dating and it doesn't work out right off the bat, it's not you. Seriously, no one finds someone straight away, it's a numbers game so don't let it get you down. But the main thing you need to work on is just convincing yourself you're good enough, because you totally are.
posted by Jubey at 6:52 PM on June 10, 2013

Just a small data point re: the thought that anyone who looks closely enough can tell you're a virgin. I've had some partners that were virgins, and I had no idea until they told me. I may have had more that just didn't tell me. It probably feels obvious to you, but won't necessarily be obvious to anyone else.
posted by RogueTech at 2:33 PM on June 12, 2013

Mod note: From the OP:
Thanks for your advice, everyone. I'll return to this thread when I waver.

It seems the consensus is that I should focus on friendships and self-esteem rather than dating (Which is not to say that I should rule out dating entirely). Luckily, I'm in therapy and my swimming lessons start in July. I hadn't thought of group therapy, but that couldn't hurt, either. I was taking improv lessons not long ago. I might return to them. I also like the idea of Toastmasters: People have complimented me on my speaking voice.

I'm using You Need a Budget to organize my money; inspired by this thread, I took an account of my expenses and incomes. Though paying the bare minimum toward my loans wouldn't free up enough money for me to move out, I could use it to take classes and whatnot. I'll look into income-based repayment.

Returning to the main question, though, I think these two comments of discopolo's are the truth:
You really don't seem to understand that the vast majority of women are kind, caring, empathetic, and really just want to be in a healthy and happy relationship with a kind, caring, and empathetic man. Not a rich guy, but a really, really good guy who tries to improve himself every day to be a good boyfriend or good husband and a good person to his neighbors and community.
But you really have to learn to genuinely like yourself and other people before attempting to have a relationship. Also, you have to be giving in a relationship, and not focused on using it to lessen your loneliness, feeding your ego, or just getting sex.
And this advice is good enough that it appeared twice:
To paraphrase Shit My Dad Says: "Son, let women reject you themselves. Don't reject yourself for them."
Self-deprecation and black-and-white thinking have been habits of mine since elementary school. Therapy, time, and effort should help me break them.

posted by jessamyn (staff) at 4:36 PM on June 12, 2013

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