Dating in Your Thirties, When You Didn't Really Date in Your Twenties. Is it Possible?

What does it mean to date in your thirties when you never really got the chance to date in your twenties? Being married at eighteen and divorced at twenty-three, I had quite a bit of baggage I carried with me. Sure, I went on a few dates and had some male company from time to time—about once a year. I didn’t want to dry up, alright? I went from being married to searching for my next husband. That clearly worked out well because here I am, thirty years old, with no idea how to date.

I knew my ex-husband for a total of nine months from the first message we sent to the day we walked into the courthouse and said “I do.” During those nine months, I was in high school, Marine Corps boot camp, Marine Combat Training, and had just reached my Military Occupational Specialty school when we got married. Romantic, right? But did we actually date? Not really. Aside from a couple of pizza outings and a night at a hotel where I got heavily intoxicated on red wine (my first time drinking it), we didn’t do much.

In high school, I never really went on dates either. I stood up my prom dates to finish a shift at the local pizza parlor. The closest thing to a date with my high school boyfriend was watching his band practice at the school auditorium or his friend’s garage. I think we went to one movie together, and even then, we were more interested in talking without his friends around.

After my divorce, I mainly did things in groups. A guy would invite me to hang out with him and his buddies, or I’d chat with my work crush during breaks. This way, I was home and present for my daughter, and my dating life didn’t cut into my time with her. So, I can humbly say I have no idea what it’s actually like to date. Maybe that’s why I’m so jaded about it and don’t understand when a guy says he wants to keep dating for a while. The whole concept just doesn’t make sense to me.

But now, at thirty, I’ve decided to give dating a try. Living in a town with a population of less than 10,000, mostly retirees, doesn’t provide a lot of options. I’ve been getting together with some guy friends, always in groups. It’s a habit I can’t seem to break, but it feels safer. Plus, if things go south, I have someone else to talk to or help out if needed.

People meet in all sorts of places, but I usually frequent spots where married couples or single moms hang out, which limits my dating life. I’ve been to the local bowling alley, usually in groups because of a specific guy I’m interested in. Sometimes, I go months without visiting the alley; lately, it’s been once every three or four months. How do I expect anything to happen if I don’t put myself out there? Has he asked me out on dates before? Multiple times. But if it’s not in a group, I always find a way to avoid it.

I dated a guy a while back who I hung out with in groups. I’m even best friends with his sister. I broke it off mainly because he was younger and always wanted to go to bars or raves, which isn’t my scene. I did go with him and his friends once, and it was everything I thought it would be. I wasn’t missing much. I’ve always been told that meeting a guy in a bar isn’t ideal. The idea that bars are where adults meet each other stuck with me.

I’ve tried the library, grocery store, dog park, and farmers market, but none of it compares to the flirting that goes on in a bar. A few drinks in, and you’ll hear all about their intentions. I still haven’t had the courage to step into a bar since that night, except for one occasion when my daughter was at a sleepover. Annoyed by some twenty-one-year-olds having a birthday party, I decided never to go to a bar again.

So, where am I supposed to meet people? Everyone I’ve dated, I met through work or Facebook mutual friends. Clearly, I haven’t had the best luck, so I want to change things up. But how? Where do I start?

Recently, I took my daughter to a waterpark. While I didn’t get anyone’s name or number, I did get flirted with. It felt odd, as a guy’s friend pushed me to keep flirting with him. We crossed paths a few times, exchanged looks, and received compliments on my 50’s inspired swimsuit. But again, I shyly said thanks and kept walking.

The journey to being ready to date might be longer than I thought, but I’m trying, and that’s what matters.