Learning to Date: Romance and the Millennial Mind

03/03/2015 03:05 pm ET | Updated Feb 02, 2016

A few months after I came out this past September, I became incredibly eager to start dating. I had already spent the first 23 years of my life not dating the people I wanted, and I didn't want to waste another second. Only, I had absolutely no idea how to go on a date.

It wasn't that I didn't know how to date girls, it was that I didn't know how to date anybody. Before this year, I had been on three real dates, and all of them were with boys I had previously spent time with in group settings. I didn't know how to go on a first date with someone I didn't already know at least a little -- a problem I believe is rather common among people of my generation.

Today's college hook-up culture has left everyone I know in a bit of a post-graduate dating stupor. In college a couple tends to go through the following progression:

  1. Become friends
  2. Begin an alcohol-assisted hook-up routine
  3. Deny that they have any real feelings for one another
  4. Reluctantly admit they have feelings for one another
  5. Go on real dates
  6. Still refuse to call it a relationship

No one I knew in college went on an actual one-on-one date with someone just to find out if they liked each other, and now, as we enter our semi-grown-up lives, we all find run-of-the-mill dating a little strange.

In college, it is easy to find people to date that you already know. Then you graduate. You move to a new city and suddenly you are no longer living in a universe exclusively inhabited by single people your age. The pool of potential friends-turned-hook-ups-turned-significant-others grows a whole lot smaller. Dating suddenly requires a concerted effort, but none of us really know how to do it.

For a while I found something wholly unnatural about going out with someone I barely knew with the explicit intention that it turn romantic. It felt so forced, too crafted to really work. And while I still don't think it is the ideal method of doing things, I know that it can work and has for many people. So I figured I may as well go for it because there really was nothing to lose.

While I preferred to meet potential dates in three-dimensional settings, I was uninterested in wandering Chicago's gay neighborhood alone. So I surrendered to an aggressive use of my Tinder account and eventually made myself an OkCupid profile.

The most nervous I have ever been for a first date with a girl was the second first date I ever had. It was a girl I met on Tinder, with whom I had been texting back and forth for weeks. It was crazy how easily we connected. I didn't think that was possible when, aside from a few pictures, she existed in my life exclusively in the form of little blue text bubbles. We talked all day, every day. She edited my essays for me. I texted her just to say good morning. We had deep talks and shallow talks and drunk talks and sober talks.

We were both new to Tinder, so I don't think we realized how crazy long it took for us to finally decide to meet. Eventually we did make a plan, though. I got to the restaurant very early, so I aimlessly wandered the aisles of the CVS next door, hoping she wasn't early, too, because an awkward pre-date run-in in the toothpaste section was the last thing my boomeranging brain needed to deal with. What do you talk about on a first date? Do I hug her when she gets here? Do we kiss at the end? How much is okay to drink? I hope a lot. Do I pay since I did the asking? Do we split it? Do we acknowledge deep things we've discussed or pretend like it's an actual first date where we don't actually know each other well enough to do that? What if the chemistry doesn't translate in person?

It is so strange how the lines have blurred regarding what it means to be meeting for the first time. In so many ways I knew her so well, yet I really didn't know her at all.

Predictably, as she was a fellow recent-grad, she also found the whole dating concept rather uncomfortable, having just ended a college relationship in which, surprise surprise, she dated her best friend. I could tell by the way she was fidgeting that she was even more uncomfortable than I was, and I knew I would never see her again.

It's sad how such a strong virtual connection can fizzle so quickly in the physical world, but even though it didn't work out, that girl was a very important step for me. She was the first time I believed that there was someone else out there that could make me happy besides the first girl who broke my heart. She was the first time I realized I was capable of liking, and maybe someday loving, someone else.

I've learned a lot of things through these first few months of dating. I've learned, for instance, that coffee dates are a bad idea because there is no clear end. You finish your coffee within the first twenty minutes, and then you just chat and chat and chat until one person finally makes up an excuse for why they have to go. Even dates that go really well have to end sometime, and coffee does not provide any sort of convenient way to wrap things up.

I have also learned that sometimes someone you like a lot who seems to be having a wonderful time with you can for an inexplicable reason never want to see you again. It isn't worth trying to figure out why. Accept that you will never know.

I was also surprised to discover how common it is to discuss past relationships or heartbreaks. I thought it was incredibly taboo, but I've learned people like being open and like hearing where you're coming from.

I am no longer afraid to go on first dates. Do I love them? No, I don't know anyone who does. But do I mind them? Not at all. The way I see it, the worst possible scenario is a slightly awkward hour or two and the best is a new girlfriend. There is really only something to gain, and those few people that do become second, third, and fourth dates are well worth sifting through the rest.

Besides, it is never difficult to find common ground with another girl around my age. Whether there are sparks is another thing, but we can always find something to talk about, especially when we can always fall back on what gay people love to chat about on dates: being gay. No matter who you're meeting, there is already a mutual understanding there, a connection because you know you each have experienced similar hurdles.

I try to go on as many dates as I can now because I believe it never hurts to give someone a chance. Someone as intent on getting out there as I am, after all, should be dating with an open mind.

The only way to learn how to date, it turns out, is to do it, and to comfort yourself by knowing that the person across from you probably has no idea what she's doing either. You have to learn to make the right choices by making the wrong choices, figure out how to say the right things by saying the wrong ones. You just have to keep putting yourself out there and allow yourself to be a little bit vulnerable. I wholeheartedly believe it will pay off in the long run.

Read the original post and more thoughts on coming out on Molly's blog, Now What? Join her as she navigates love, Tinder, adulthood, and identity.