Reply To: That very first date

Here are a few things I’ve learned that made dating way easier (and a lot more fun). Hopefully, some of this helps you too.

The day before the date, write out some good questions or topics, keep them in your pocket (literally or mentally). If the conversation goes dry mid-date, excuse yourself to the bathroom, check your notes, and come back ready with 15 new things to talk about.

Put actual thought into these questions. Dates are noisy, unpredictable, under pressure. Do the heavy lifting ahead of time so you can just enjoy the moment. You’ll feel way more in control.

If you struggle with loud or overstimulating places (like I do), fine dining is a great workaround. Where I live, it’s about $30 per person for food, but worth it. You get a quiet, dimly lit environment included with meal. No birthday parties two tables over bashing a gong in celebration, no TVs blaring, just focused conversation. Totally worth it.

I’m in the same boat feeling out of sorts when the context isn’t clear what the date is. I can’t go on the date unless I have that information. Know where your coming from!

I’m not into the whole sex on the first date thing. I put a stop to that in my 20s. Just doesn’t do anything for me in that context, feels empty.
That said, I do follow the three-date rule. If there’s no physical connection by then, I move on. It’s important to set boundaries that make sense for you.

I used to rely on online dating profiles back when people actually filled them out. In the mid-2010s, those about me sections were gold. You could tell so much about someone before meeting up.

Now? It’s all blank profiles and emojis. It’s approaching 2026 and the tools are still gone. Honestly, I get more info from talking to someone in person now… and that’s the problem. It’s not enough! Lol.

I have a pretty strange dating test that works great.

I enjoy being humorous and goof during my time off, need to make sure I find energy that matches. This has been my play for 30 years.

During the date I’ll playfully shoot the straw paper off the straw on to the table so it bumps her arm (aim down so it hits the table first, then her arm).

That reaction is the test. If they glare across the table in judgment they failed the test. If they shoot one back, that’s who I’m looking for. If they just smile, they are at least polite, that’s good!

This test has treated me well. The three that passed, the relationships lasted more then a decade each. But, prepare for glare! That sounds like a meme.

If you don’t like going to new places, the stress of finding parking, traffic patterns and limited working memory etc. There is a work around.

Spend a day on google maps. Set a 20 mile radius. Pick places in all directions from your location, so where ever the date might land you have a spot picked out already, know how to get there, the parking situation, etc. You vet them ahead of time so you know the environment will be a present one. Invest in success.

Hopefully some of that helps. These little workarounds kept me sane.