Should I date now, or wait until some life improvements I'm working on come to fruition?
June 23, 2012 8:51 AM   Subscribe

For the first time in my life, I feel confident enough to start dating. Thing is, my life situation isn't great at the moment, but should hopefully be better in the next 3-6 months. Should I actually start, or hold off?

First, the bad things: I'm a 27 year old male virgin. I live with my dad in a disaster mess of a house. I'm about a hundred pounds overweight. I've never even so much as kissed a girl. In short: stereotypical basement nerd. For a long time, I've just been blindly moving forward in my rut, doing a (frankly) mediocre job of running a small web consultancy, playing video games, thinking woefully about myself, and pretty much sticking to my not-particularly-outgoing routine.

However, fueled by a gradual series of realizations and positive experiences, I've finally started to break out of the above. I've lost 40 pounds and am committed to slimming down. I've made plans to phase out the business and take a position with one of my clients within the next several months, improving my money situation to the point I can move out. Most importantly, I believe I have a much more positive attitude about myself and what I have to offer: I've traveled a lot, I've had an unconventional upbringing that gives me a unique perspective, I'm good at conversing with people, and overall I am a positive, helpful person. (Always have been. Just not always towards myself.)

But, still, I know I have a lot of work ahead of me on improving myself. There's a manageable but significant amount of debt I need to pay off, some minor but important health and style issues that need to be addressed, and I really don't know if I can comfortably bring anyone back to this house without some major work. (Not to mention just being kind of embarrassed about never having moved out in 27 years, y'know?)

So, herein lies the question.

As mentioned, I have never been in a relationship before - indeed, I've never had sex or even so much as kissed someone. But for the first time I think I have enough self-confidence to actually start dating, to handle potential rejection, and not to go completely head-over-heels with the first woman who lets me into her bed.

I want to make it clear that this isn't about wanting desperately to be loved or fulfilling some internal need I think I have. I'm just bored with not having dated for so long, excited to be feeling so much better about myself, and really just wanting to finally get out there and meet people. Even if I have some failures, I think I'd really be satisfied to just have the experience. And if a relationship works out on any level, someone to talk to about some of the things I've been going through would be great; while I have good friends and I do talk some about this stuff, none of them are on a level where I talk too much about what I've been going through. (I've had such close friends in the past, though we drifted apart during long periods of travel.)

I actually already started dabbling. I set up a profile on OKCupid, messaged a few girls, received responses, and event went on one first date. That actually went really well, though we wound up not having a second date due to circumstances on her part.

Despite that, I've been having some second thoughts. Not in a "OMG I suck" kind of way - like I said, I'm actually really confident about my future prospects right now, and I'm genuinely eager to get out there. But if my situation isn't going to improve dramatically for another few months, and for now I have this list of things that are traditionally turn-offs… is it better to hold off until I've laid more groundwork and actually have more concrete to show about myself? Or am I making too many assumptions about what others might think - should I just get out there, let people see who I am, and let the chips fall where they may?

Part of me thinks the "wait" side is just self-doubt coming out to show itself again. And part of me thinks the "get out there" side is just being impatient, and that I'd have a much better chance with women that interest me if I weren't still living with family in a messy house while closing a business.

I realize there may not be a "right answer" here, but I feel like I've gone around in circles in my head in the past week! Any additional opinions folks can offer here would be really helpful.

And, finally, apologies for the long-windedness… perhaps I'm being self-centered, but I felt like some of the details here might be important, and as an anonymous question, it's a bit harder to clarify.

Not sure if this is strictly necessary, but if anyone wants to get ahold of me, they can do so at
posted by anonymous to Human Relations (23 answers total) 13 users marked this as a favorite
Don't wait "until" to start doing the things you want. That's a classic way to put off things you think you don't deserve.

Date. Live your life the way you want to. You deserve it.
posted by xingcat at 8:56 AM on June 23, 2012 [26 favorites]

Listen to xingcat for he speaks the truth :)

Your current living situation might put some people off, but so what? You know it's going to change soon, because you're getting your life together so if you get knocked back because of those issues, you know that they're going to change soon. Meantime, maybe there's someone there right now who'd be delighted to go out with you & doesn't care about any of that stuff! It's win, win all round in other words.
posted by pharm at 9:01 AM on June 23, 2012

Stop waiting for your life to be perfect! You might have a better chance in 3 weeks time (for example) but why waste the next 3 weeks? One life, one chance, etc! Get out there and make the life you want :)
posted by lifethatihavenotlivedyet at 9:03 AM on June 23, 2012 [2 favorites]

Go now. Waiting until whenever just means that you'll build up more anticipation and all the stress that goes along with that. And while this might not be to everyone's taste, you could get some sexual experience by paying a professional, if for no other reason than to get the first time jitters over with.
posted by Ideefixe at 9:04 AM on June 23, 2012

Don't wait. I have a friend who is around your age in similar circumstances and he's been waiting for damn near our entire friendship, and it makes me so sad. You may have some things that turn off women you'd like to date, but guess what? Those ladies are going to have things that turn you off too. While the "things" may change over time, that fact that there just will be some incompatibilities just not going to change, regardless of what life improvements you make.

But here's a pro-tip: having a plan and following through on it is a major turn on and it works far more in your favor than "wait and see."
posted by sm1tten at 9:12 AM on June 23, 2012 [4 favorites]

Don't wait! You're already on a great trajectory, and have momentum built up. Use it to your advantage!
posted by Fig at 9:54 AM on June 23, 2012

When I was 27, I dated a guy who had a bit of a rough patch, but who was on the upswing. He had a major depressive/suicidal episode in college which cause him to move back in with his parents. By the time I met him, some 6 years later, he'd graduated from a local college and gotten his first job, but he was still living with his parents and trying to manage his depression. He was honest with me about it and I respected him for pulling his life together. We only ever came back to my place because going to his parents would have been awkward. He moved out of his parents place maybe 8 months after we started dating (he did invite me to move in with him which would have been a mistake--- live by yourself first!!). We broke up for other reasons, but ten years later I still respect him for accomplishing so much after such a hard time and he's grateful to me for helping him through a difficult time, and we're still friends.

So I would say start dating, but be honest. You've accomplished a lot and you're working on bettering yourself and the right girl will see that. Trying to deceive or cover up will start you off on the wrong foot for having an honest and trusting relationship.
posted by bananafish at 10:02 AM on June 23, 2012 [2 favorites]

I can't speak for all women but I know I'm more likely to give the benefit of the doubt to someone who is actively working on stuff. You're overweight but enjoy walking around downtown with me? I'll cut some slack. You're in a not-great living situation but you're busting hump getting your business squared away and the home life is next on the to-do list? Okay, I'll stick around to see how it turns out.

Nothing is less attractive to me than complacency (except dishonesty) and nothing is more attractive than get-up-and-go-ism. You are working on intransigent problems and making great progress! Use the positive changes to fuel more positive changes and let your enthusiasm show to the girls you date.
posted by workerant at 10:19 AM on June 23, 2012 [2 favorites]

I really don't know if I can comfortably bring anyone back to this house without some major work. (Not to mention just being kind of embarrassed about never having moved out in 27 years, y'know?)

Separate from the "should I date or not date" question, I would point out that PLENTY of people live in shared housing situations, which is both cheap(er) and conducive to dating, and I hope this is on your short to mid-term agenda.

But I am with everyone else is saying "Go forth and date!" The statistical odds are that most first dates don't really work out anyway but honestly the more dates you have, the better you get at it.
posted by DarlingBri at 10:40 AM on June 23, 2012 [1 favorite]

Generally speaking, women love a guy working on himself rather than a guy wallowing and waiting for things to be perfect.
posted by Ghostride The Whip at 11:04 AM on June 23, 2012 [2 favorites]

If you try, the only bad thing that will happen is that maybe some women won't be interested in you. But this will happen anyway! Nothing to worry about - go forth!
posted by Ragged Richard at 11:28 AM on June 23, 2012

Unless you are the most incredibly lucky man in the entire world, you aren't going to meet the one right away. Start dating now. You don't have much experience. Commit to making mistakes and learning from them for the next 6 months. Go out with as many different women as possible (without sleeping with them) and find out what your type is.

Ask lots of questions. Challenge yourself to know as much about each ladies personal story as she will tell.

As a woman who dates I can tell you, we don't expect much of where you live. In the beginning of a relationship, I am more interested in how a man treats me than how he treats himself.

Good luck! Have fun!
posted by myselfasme at 11:53 AM on June 23, 2012 [1 favorite]

Get out there and date! But since the house needs major work, why not do that as well? It will make you feel better about your living situation every day, is a nice gift to leave your dad, and housework and remodeling can be good physical exercise.

Good luck!
posted by cyndigo at 12:52 PM on June 23, 2012

During my divorce, I saw men. I never once brought one home. We met elsewhere. Your living situation is not a show stopper.

The only reason you should consider maybe waiting is so you aren't shooting too low-- by that I mean that women who would not give you the time of day now will after you have achieved a few more goals. I don't really think that is a reason to wait (for one thing, I always like knowing up front who the shallow jerks are so I can avoid them). I think that is a reason to not let anyone treat you like a pity fuck.

My advice: Go out and get a little experience. Promise yourself no serious commitments until X (moved out, making better money, lost 20 more pounds -- whatever makes sense to you as a benchmark). Enjoy yourself. Live. Learn. Grow. Don't turn this into a big deal.

Have fun!
posted by Michele in California at 12:57 PM on June 23, 2012 [2 favorites]

I think you should go ahead and date now, with one crucial caveat: are you in the right mental space and do you have the mental space in your life to be able to focus on a date and enjoy being on a date while you are on it?

That's not worded very well, but here's what I'm trying to get at. In the month or so before I took the bar, I was completely preoccupied with that. I mean, I didn't want to be. But I went on one or two first dates during that time, and I realized that I just didn't have the mental energy to get to know and have a conversation with someone new. Chilling with very good friends was about all I was capable of. So my only question is: Is unwinding your business that thing for you? Is it your bar exam? If it is, you may find that you're not capable of dating. Otherwise, get out there!

Life is way too short to wait until you're in the perfect place and who you want to be before dating. Life is a journey, and you may find that it takes a long time to "get there," or indeed that you never do -- I find that it gets more and more complicated as time passes, and I often suspect that no one ever really has their shit all "figured out."

On a more pragmatic level, you are already taking concrete steps to lose weight, move out, and get a better job in the short-term future. I think you will find that this matters much more (especially with anyone worth knowing) than do the facts that you currently are still overweight, living with your parents, and underemployed. The key is taking steps. It shows ambition and motivation and all those things that are really more important than some immediate circumstances which, frankly, aren't the end of the world.
posted by J. Wilson at 1:13 PM on June 23, 2012 [1 favorite]

Meet friends - not girlfriends. Start with just that, do activities (walking) together - see if something more develops.

You are on the right-path. Do not wait as others have mentioned - waiting will then bump you back into the rut.

I know, because... I am currently waiting...

My situation is slightly different, getting a divorce after 17 years, but I feel I cannot actually start my life, until the situation between the wife and I has at least moved forward (we still live in the same house...). It is bothersome and at times depressing.
posted by jkaczor at 1:32 PM on June 23, 2012

Take things as they come. If you date some folks and things click, be honest. Explain that you can't go to your house, if push comes to shove, learn to love coffee at Denny's for those "into the night" conversations.

You'll be out on your own soon enough.

I'm enough of a neat freak to appreciate that you don't want to bring anyone into a gross house. You must be a great guy to see that and want to act on it. Go with that instinct.
posted by Ruthless Bunny at 1:41 PM on June 23, 2012 [1 favorite]

I will add that I was still living with the future ex and our two kids while getting my toes wet. None of them knew I was seeing anyone. (My ex had laughingly told me "This is California. It won't effect the divorce. Do what you want." But I felt it would be rude to not be discreet about it. We both seemed to adopt a "don't ask, don't tell" policy.) None of the men I saw ever cared about my living arrangements. So I don't see any reason to make a big deal about it, given that you expect to move out soonish.
posted by Michele in California at 1:59 PM on June 23, 2012

The chances of you ever feeling like, "yes, everything in my life is perfect, all is arranged, time to find a partner" are pretty low. There's always something. People lose jobs, get jobs, move house, have sick friends, have friends who are getting better, get sick themselves, recover themselves, and on and on; people are in motion all the time. Own your own mobility, and the mobility of others. No one's ever finished with their stuff. You're going to meet people who are awesome but going through their own series of changes. That wouldn't put you off meeting them. Why should your stuff put them off meeting you?
posted by Errant at 2:22 PM on June 23, 2012 [6 favorites]

I completely understand and empathize about wanting to wait. Try not to get ahead of yourself, though. I get that you want to be a good partner to someone, with responsible spending habits, positive actions regarding health, and other qualities that you also would like your mate to have. But you're good the way you are: honest, considerate, hopeful about the future, interesting, a good conversationalist. Woudn't you want to meet a woman with those qualities, with the same "minuses" you see in yourself?

I think the style thing is something you can start now. Sure, you'll improve your wardrobe over time, but there's no waiting involved if you just pick out a pair of pants that really fit your current size, and a couple of shirts in colors that flatters you. After losing 45 pounds, you need a new belt -- get one that fits you one the outermost hole :-) If your shoes are shabby, get a new pair. Many, many women, have just one or two "first date outfits." You just need a few things that fit well, look fairly new, and that you feel pretty good in.

It sure would be nice to have a woman visit your home, but as others have said, it's not a big deal. I'd say, don't even mention at first that your home isn't visitable. Bring it up after a couple of date, when you and she start to feel like spending more time together.
posted by wryly at 3:51 PM on June 23, 2012

As a female, I would go out with a guy who lived with his parent as long as he had a plan to move out. There are two types of people in your situation: those who are actively working to improve themselves and those who *say* that they're improving but have tons of excuses about why it isn't working out. It sounds like you're serious about improving your own life and good on you for doing that. Your life doesn't sound like a deal breaker now as long as you stick to your plan and keep moving forward. By the time you and some lucky lady get serious, you'll be that much closer to your goals.
posted by bendy at 8:04 PM on June 23, 2012

I asked a similar question a couple months ago. I ended up trying it (Okcupid) and now i'm dating a really really sweet guy (their matching system is crazy good ?!).

I think you should go ahead with it. you seem a bit hesitant and self-critical, both of which show that you think things through before you act, which is a good thing.
I don't think you should hold yourself back any longer-- if you feel ready to start trying, go ahead.

worst case scenario, you meet someone and it doesn't work out, you decide to work on your own life first before you date any more. but at least you have some experience, maybe even with sex, and it will be less daunting for you in the future.

best case scenario, you meet someone in a similar life situation, you click, and then you can both help each other move forward in your lives all the while enjoying the bliss of being in love.
posted by costanza at 8:26 PM on June 23, 2012 [1 favorite]

the world places far too much importance on appearances and "having it together".

for all the world knows, you could be a far better lover and partner than some six-pack jerk with a mercedes. your own happiness is at stake here, so why wait any longer?
posted by costanza at 8:35 PM on June 23, 2012 [1 favorite]

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