Help! I’m Having Trouble Meeting Someone

Were you mostly single in your 20s before meeting Conor? I’m recently single and am absolutely terrified I won’t meet someone I click with as much as the last guy. Any advice on how to get over that fear and meet someone? I also don’t love going out and getting drunk until 2AM which is what most people do to meet people.

I am hardly a dating expert. In fact, I’m pretty sure I was awful at it most of the time. But a few readers have asked for my advice on dating so I want to talk a little bit about my experiences and what I learned the past few years.

My first real relationship began when I was 19 and didn’t end until a few months before my 29th birthday. I was a year away from 30 and had dated one person (who happened to be the worst so I had never had a “good” relationship) and was a. terrified and b. sure I would never meet anyone. Then bam–single in a new city.

Those first few single months were fun–I was on my own and went out all the time but it wasn’t long before I remembered that I don’t love bars or staying out past midnight. And I’m not even almost decent at flirting, so there’s that. There was the one time I smooched some soccer player from SF who was in town for the weekend but I never left a bar with someone since that’s just not something I ever would have done. And I never met someone at a bar and actually dated them, either.

This can lead to meeting someone but I never saw it as the optimal way to start something new.

I date all the time but it’s the classic tale of dating these days. I seem to find myself wanting guys that want nothing to do with me and vice versa.

After a few failed dating experiences, I finally figured it out. We play it cool with the ones we’re not interested in so naturally, they are almost often more into us, and we can get a little “ah he’s perfect I need to date him” with the ones we do like and no one likes that.

There were the times I loved being on my own and others when I felt so lonely and was certain I’d be alone forever. No one likes that desperate to find someone vibe

Dating was an emotional rollercoaster, or at the very least, I was an emotional rollercoaster. I’d leave a fun first date, build the guy up, and when things didn’t pan out, I was sure I’d never meet anyone else. Really think about why you like someone so much early on and actually get to know them before deciding how wonderful they are.

If someone lets you down early on, cancels regularly, or isn’t making an effort, they’re probably just not that into you so do yourself a favor and walk away. While it’s fine to start a conversation, you shouldn’t be the one initiating everything. I can’t tell you how many times I did this. Looking back, I’m like…

I’m struggling with the idea of dating again. I’ve been single for way too long and feel like I don’t know how to meet guys.

Setups never really did it for me but I was always open to them, and you should be, too. Most of the guys I dated for anywhere from 2-4 months I met online, and as most of you know, I met my fiancé on tinder. And I met him when I wasn’t going through one of my “I’m desperate and need a relationship” phases, just weeks after this happened.  Say yes to new plans and experiences where you might meet new people, go out–but maybe to happy hour instead of until 2AM, or try a new class or group activity. And there’s always Tinder, Bumble, and other dating apps.

If you want to meet someone, be open. Consider the things you have on your dating deal-breaker list and maybe reevaluate how important they actually are and don’t write someone off because they’re not tall enough, don’t have the “right” job, or aren’t what you imagined them to be. No one is perfect, including you. And be open to how you’ll meet someone. I was always open to set-ups and only had 3 or 4, but they didn’t work out and did plenty of online dating, too.

One last point. Finding someone to share your life with is great but it shouldn’t define your happiness. Do what you love, spend time with people that make you happy, and don’t give people more credit than they deserve. I found that when I went into dating with a breezier mentality, I put a much better vibe out there and that usually attracts the right people.

Do you have any questions about dating or lessons learned that you’d like to share? Leave them in the comments below! 

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  • I love all your posts. This one really hit home with me. I was with my ex boyfriend from 19-30 and it was the worst relationship. I put up with so much unacceptable behavior. I too feared I would be alone but then I realized that I felt that way because that’s how my my ex wanted me to feel so I wouldn’t leave the relationship. It’s funny because once I was ok with being alone and perhaps not finding the one and was ok with that, that’s when my current boyfriend came into my life! He is so amazing and sometimes I am thrown off by how great of a guy he is. I’ve actually known him for a very long time as we are from the same town. It was perfect timing. The advice I would give is that when you are ready, the right one will walk into your life.

    1. Hi Marche! I’m just seeing this comment. I went through the same EXACT thing! He was so awful and I don’t know how/why I put up with it. I’m so glad you found a great guy! You deserve it.

  • Sage advice here, Danielle. I’d like to echo your final important paragraph as a single woman in my mid-thirties, especially for any 20-something readers. It can be so hard to fight loneliness when it feels like everyone around you is coupling up, but it really is true that while a romantic partner might add to your happiness, it really shouldn’t define or even limit that happiness. About a year ago, during a period of marked self-pity about my lack of love, I had a sudden conviction that I was massively limiting my definition of love. I have so many people to love in my life–family, friends, my friends’ children and family members, my students, pets. That’s since been my comfort go to: I’m not lacking love–I’m literally surrounded by it. Romantic love is a wonderful thing to have and desire, but it’s just one sliver of all the love the world has to offer. I think opening yourself up to love can mean so much more than just dating and romance–and it has the added benefit that you’ll be open to romantic love too, if and when you find it.

      1. Agreed! Back when I first started blogging in 2007, my blog was called “Well that’s just fabulous” after this quote (via Carrie Bradshaw / SATC)

        “The most exciting, challenging and significant relationship of all is the one you have with yourself. And if you can find someone to love the you that you love, well, that’s just fabulous.”

    1. I couldn’t agree more! Whether you are in a romantic relationship or not…the most important love of all is the love for yourself.

    2. This gave me chills! Thanks to all of you ladies. I’m finding a version of love right here on this blog 🙂