4 Things To Do On A First Date

Last weekend I went on a first date with someone I met online. We got off to a good start. Both of us were on time and dressed appropriately. We were an instant hit and did all the right things to do on a first date.

He was willing to roll with it when I suggested a date during the Super Bowl (I am not a football fan but I did offer to reschedule when I realized the timing might be inconvenient) – which I interpreted as a nice sign of interest.

We just had a casual date planned: admiring the snow sculptures from a recent competition. It gave us something to talk about and a reason to walk around.

However, whether due to nerves, wildly different senses of humor, or a head injury (I wish I were exaggerating when I posit this as a logical explanation), the conversation suddenly became so off-putting that I couldn’t wait to get away.

Things To Do On A First Date


If you don’t want to find yourself in an awkward first date situation just like me, try the below 4 steps.

Do not waste time complaining


Twenty minutes into our date he began to complain about the quantity of sculptures available for our amusement. Choosing to focus on the lack of quantity rather than marvel over their quality (some of them were incredible works of art).

His complaining revealed him in a petty and negative light. It also didn’t add much to the conversation: I certainly didn’t want to denigrate the art I was enjoying. So after a few attempts to point out my favorite parts of the exhibit, I just tuned him out and tried to enjoy myself.


Do not argue about ridiculous things


When I mentioned that I teach skiing part-time, my date went on and on about the rivalry between ski school and ski patrol. This isn’t a thing. I tried to explain that to him and pointed out that I was a patroler for several years so I’ve seen both sides, but he was adamant that the two groups could not coexist.

He reasoning? He saw it in a movie. It was surreal to have someone hold and insistently defend such a distorted view of a subject I was far more familiar with.


Do not flaunt your crazy


Midway through a story about a trip to Alaska he interrupted himself to tell me that he had absolutely no idea why he went there in the first place. I hadn’t asked why he went there, nor was it relevant to what should have been an interesting anecdote. Instead, he just took a moment to point out that he didn’t have much of a grip on reality.


Do not devote valuable time to your egregious failures


This guy was a real estate investor who specialized in flipping houses. He recently bought and renovated a home in a different state, in an unfamiliar market, with borrowed money. The more he talked about it, the more he displayed his poor judgment. We all make mistakes, but there is no need to point them out on a first date.

I haven’t called him for obvious reasons. He hasn’t called me either, which given the amount of enthusiasm he showed for a second date, only confirms my head injury theory. He may have ended the evening in urgent care with no memory of meeting me.

What’s some of the worst first date conversation you’ve experienced?

“I once had a date that was going very well until she would not shut up about how disappointing it was that the restaurant only offered gorgonzola dressing instead of the bleu cheese dressing she wanted. I refrained from screaming that they are the same damned thing! but I did not call her again.”

“A few years back my date treated me to a twenty minute monologue about his failed restaurant and his mean business partners. I literally could not get a word in for twenty minutes. When he finally wrapped up, I told him I didn’t think things were going well and left. The date lasted less than half an hour.”

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