The Key to a First Solid Gay Date Isn’t What You’d Expect

gay date first date two guys on a date

“So what does your brother do?”

The moment he asks me that, I know the date is dead. If the conversation has lulled that much, that he’s resorting to asking about my sibling’s occupation, then there’s no way in hell there’s going to be a second date.

Like every gay/bi man out there, I’ve been more first dates than I can count. I’ve done dinner, coffee, movie, brunch, live music, museum, gym date, sex then dinner after, and of course, drinks.

Recently, I went on one of the best first dates I’ve ever had with a guy. Now he is pretty awesome. I’ll give credit where credit is due, but I also think the nature of how we approached the first day really made it something memorable. Something special.

So what did we do? We didn’t stick around in one place for more than a couple hours.

But before I get to that, let me briefly tell you our origin story. He was a server at a restaurant downtown I go to, and I remember thinking he was really cute. Then, we kept seeing each other at the gym and smiling.

I couldn’t place exactly where I knew him from, but was positive I knew him from somewhere. Then at a pride party, we ran into each other and formally introduced each other. A few days later he messaged me on Facebook, and a few days after that I was inside of him. (Okay, that was kind of a spoiler, but yes, the date went really really well.)

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Alright, now that I got the origin story out the way, I can talk about how crucial not staying in one place is for a successful first date.

We first started the night at my apartment. We had two drinks to loosen us up. The moment there was a little break in the conversation, which occurred after answering the mandatory “How was your day?” and “What have you been up to this week?” he suggested we go to his friend’s band show.

To be honest, when he first told me that we have to see his friend’s band perform, I was not thrilled. The last thing I want to do on a first date is be stuck listening to a loud, untalented band with a guy I just met.

Reluctantly, I agreed. Once there, we both immediately ordered a drink. Then we went to the backroom, and thank God, the band was good. We ended up dancing our butts off. Once we got tired of dancing, we didn’t stick around.

ditched on a gay tinder date
Ditched on a Gay Tinder Date

I didn’t pretend I wanted to be there a second longer than I actually did. We headed back to my place for more drinks and to change quickly. We were heading to a pride party and wanted to put on some short shorts and heels.

When we got to the bar where the pride party was happening, we did everything. We did the kissing booth. We took (a lot) of shots. My friend works as the bartender there so she doesn’t charge me. Then there was karaoke in the back room. Drunkenly, I sang and absolutely flopped, picking a song way out of my range. (I picked Beyonce’s Love on Top for those of you who are interested.)

When we had done all the activities the bar offered, were tired of drinking, and were growing bored of the bar altogether, we headed back to my place. My housemate was up with her boyfriend, so we all chilled for a little bit, but when we were done chilling with them, we went back to my room. There, we had ridiculously hot sex for about two hours.

The thing about this date, which by now, I’m sure you can tell: We did shit. We did a lot of fun, cool things. We saw a live show. We got dressed up together for Pride. We sung karaoke. We partook a kissing booth. He met my housemate and her boyfriend and we chilled with them. And after all that, I took him straight downtown to poundtown.

Stagnancy, is my opinion, is what ruins dates between two guys, who otherwise, could be a good match for one another. First dates, more often than not, are painfully contrived. We think we need to get to “know” the other guy, and the best way to do this is through a nonstop interrogation of questions.

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This is one way to do it. But what’s more important than his favorite color, is if you like his personality. Is if you have fun with him. It doesn’t actually matter if he’s from Southern California or the Midwest. Yes, of course it’s interesting, and where he’s from will undoubtedly influence how he acts. But if you like his personality —  if you jive well together — if he makes you laugh — then the rest will come later.

There’s no reason to load up on unnecessary details from the beginning.

Another thing you’ll notice on this date is that we weren’t afraid to drink. Needless to say, I don’t want to encourage alcoholism, and you obviously don’t need to have a single drop of alcohol to enjoy a first date.

That said, it does help loosen you up. Drinking gets you silly. It relaxes you. It makes first dates less tense. (Again, this is all in my opinion. I’ve noticed having a few drinks on first dates really helps me, but I know this wouldn’t be for everyone).

So the next time you have a first date, be spontaneous. Go from bar to bar. Don’t stick around in one place for too long. And most importantly, see if he makes you laugh instead of seeing what his brother does for a living.

1 Comment

  1. What a great, no-nonsense article. I planned something similar for my husband, who was living in Orlando when we met, when he came to visit me for the weekend. Six years later we are still together.

    I’ve found this type of date a refreshing change than dates where they take place in one or two settings (e.g., the bar and then the bedroom). We are dynamic creatures with varying attention spans and interests. We owe it to ourselves to have fun rather than sit through a 2-hour movie with minimal time to interact with each other.

    For our first date, I crafted an itinerary for different hotspots in the city. My husband hadn’t spent much time in my city before, so I picked a few spots for us to visit since he was staying only overnight and had driven nearly 3 hours.

    The first place we went was to a small tapas place 3 blocks from my then-apartment. If you’ve had tapas, then you know there’s opportunities to talk, share, and enjoy each other’s company. After two hours, we were ready to grab a few drinks at one of the gay watering holes. We shot a few rounds of pool before we left to get dessert and a glass of wine. After that, we went to an illuminated public water fountain with 100-foot high shooting jets that provided panoramic skyline views. At the end, we came back to my place for a recap.

    The time flew by quickly, and we both had a blast.

    If your date seems to be headed on a one-way trip to Boring Town, go ahead and throw out ideas that change venues and things to do. It also never hurts to have a few backup ideas: whether you use or wait to do them, there will always be something else to try.

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