I’m In My 30’s And Still Single. What Am I Doing Wrong?

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Hi Barbara,

I’m not really sure why I’m writing you. Actually I am. I need to feel ok with being single at 33 while still maintaining hope that I can find a solid, real, lasting relationship.

I embrace being single. I appreciate being on my own and dictating my own schedule, I do a ton of yoga and look great (might sound conceited but it’s true), I own my own successful business, I own my house, I save money, I travel and pursue things that are interesting. I believe strongly that I can’t and won’t settle until it’s RIGHT.

I’m admittedly scared that that conviction will keep me from being in a happy relationship because I’m asking for too much or won’t know “right” when I see it. At the same time, I seem to keep getting hurt.

There’s a pattern – I date a woman for a month or two. In the beginning, it’s always her pursuing me hard. And then I let my guard down and start to like her, start to think about a future with her, and then, like clockwork, she backs out. I really don’t understand. I know that you have said over and over that we shouldn’t try to draw some sort of conclusion about rejection, but I am struggling here!

Most recently, I was seeing this woman that I was very interested in. True to form, she worked hard to date me while I was not so sure at first. After about a month and a half, I thought things were going great. I had to go out of town for 10 days, for work and to take care of my mom who’d had major surgery. We texted or called each other every day when I was gone. When I got back, rather than making plans to hang out for an evening, she wanted to stop by for sex on the way to a party that she “had to make an appearance” at. I suggested hanging out another time when we could actually spend time together rather than be rushed. She said she understood but basically I never heard from her again.

Maybe I hurt her feelings? I made it clear that I wanted to see her, just was not really ok with those circumstances. I love sex but I felt like a “layover” (ha, ha) on the way to her obligation or good time. I knew she’d been busy at work but in her shoes, I would have made time, invited her to the party, not gone, something else.

Even though she put a lot of time in in the beginning—hanging out every day, calling and texting all the time, telling me how much she liked me, etc., etc. The worst part is that I still really like her! I can’t shake the idea that I was too demanding or inconsiderate.

Am I trying too hard? Not trying hard enough? Do I need to lighten up? Be more blunt? Do I get attached too quickly or not quickly enough?

I’m really trying to just be myself and see where it takes me, but these little episodes where I date women who disappear is messing with me. They make me question how great my single lifestyle really is, question my approach to dating, get my hopes up and let them down.

Hello reader! Let me start by saying that it seems like you have a great life for yourself already. Are you sure you want to be in a relationship? If I had my stuff together as much as you seem to have yours, I’d probably prefer being single!

All jokes aside, I do understand that the single life can get lonely sometimes. Especially when you are independent and have a great life for yourself, it’s hard (or even impossible) to bring yourself to “settle” for someone who doesn’t fit.

Yes, I do talk a lot about not letting rejection define you. And that’s an important thing to remember, too. I know, I know – easier said than done. But this cycle you seem to be in tells me that maybe you’re just picking the wrong women for you. That doesn’t mean there’s anything wrong with them, or that there’s anything wrong with you. It just means that you’re not right for each other – and that’s what dating is all about.

You see, the purpose of dating is to find out whether you want to spend your life with someone or not. At its simplest form, dating isn’t about definitely spending your life with someone – that decision won’t come until later. If you really do enjoy your single life (aside from the loneliness), maybe you need to re-evaluate your stance on the issue.

Here’s how it stands from what I gather:

  1. You enjoy being your own person, and need a partner who can complement this, not complicate it.
  2. You don’t need a girlfriend, you want someone to enrich your life a little more than the already-rich-and-wonderful life you’ve built for yourself.
  3. (Now, this one is just an assumption, so please forgive me if it comes out wrong:) I think you’re looking for girls you don’t have enough in common with.

I know, it’s hard to find out how much you have in common with someone right away, and that’s what dating is all about. That first month or two is a time for getting to know each other – which you’ve done! – and then, quite often, we decide that we’re not compatible after all.

This has something to do with the fact that we form our attractions primarily based on physical appearance. There’s nothing inherently wrong with this, no matter what anyone tries to tell you – it’s human nature to find a partner who is attractive to you. No one can force or coerce you to be with someone you’re not attracted to.

Unfortunately, the side effect of our basic human instinct is that, sometimes, the attraction is all there is. To me, it sounds like this is the case with your recent interest. She was attracted to you, you were attracted to her, you both put in a lot of work, and then when something came up that wasn’t “attractive”, per se, she bailed.

I do want to take a minute to address what you would have done. While some of these do sound like Great Girlfriend Choices, there’s a saying: Hindsight is 20-20. It’s easy to say what you’ll do when it’s not you having to make the choice. This mostly pertains to the “not gone” part of it – maybe this party really was something important, whether she was telling the truth about why it was important or not, obviously it meant something to her, right? If you were really in her shoes, you would probably still have gone.

Next, she should have either made time for you or invited you to the party – I definitely agree with you there. However, maybe the party was invite-by-host only, in which case she wouldn’t have been able to change her plans at the last minute to allow you to come. That leaves one real option of what she should have done: Made time for you, too.

But, of course, it’s not really that simple, either. (It rarely is!) You say she’s busy, so maybe that’s the problem, but if she completely stopped talking to you when you requested a reschedule (I hate how formal that sounds!) then the problem probably lies on her end.

I don’t think you’re trying too hard, or not trying hard enough – just that you’re reading too much into it. If you’re really happy on your own, maybe it’s best if you keep it that way for a while. It seems cliché, but the right person will come along when you least expect it, and the harder you look for Mrs. Right, the less likely you are to find her. That sounds hopeless, but it shouldn’t, really.

If you want to help things along, you could try setting up an online dating profile. I know Match has been advertising lately that 95% of their users are happy being single, but open to dating the right person – and in my opinion, this is where you should be in your life right now. The single life definitely has its own perks, after all, especially when you already know what you want.

There’s also no such thing as “getting attached too quickly” or “not getting attached quickly enough”. You can’t really help how soon and how hard you fall for someone – although there are things that people do to try and help control the situation. (In my experience, they don’t usually work, especially once sex enters the equation.)

Perhaps the best approach for you would be to stop worrying about finding a girlfriend for now. Maybe set up the online dating profile and see where that goes, but it sounds to me like you can afford to be pretty picky. Just lay out what you want in a partner, along with your best qualities, and maybe one or two not-so-great ones, framed like you would in a job interview. No one believes anything that’s 100% positive, so if you don’t let a little flaw show through, people will probably think you’re catfishing them. I mean, don’t put on there about that one time you forgot your toothbrush when you went to camp as a kid and didn’t brush your teeth for two weeks, but I’m sure you know what I mean.

My last bit of advice for you is to not let these women get your hopes up. You should never rely on expectations from others – especially when you’re handling your own expectations of yourself so well. It seems to me that you’re a bit of a secret romantic, which is a tough spot to be in when you’re also so independent. (You’re not doomed, though, I promise!)

My final verdict: Try setting up an incredibly-descriptive online dating profile (but no personal information – that will come later). Be selective about who you agree to go on a date with; you can definitely afford to. Then, when someone starts to seem just right for you, don’t jump in head first. If you’re worried that it’ll be all about sex, try holding off on sex for a while! If you’re worried that it’s about your money, don’t agree to meet up with anyone who doesn’t have their own. As much as we value the face-to-face connections we have, it really is easier online.

Do me a favor, and if you do decide to go the online dating route, take a look at these articles (if you haven’t already):

Take care, reader, and please let us know how it works out! I’m always here to answer your questions.

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