Dating Experiences From 50 First Dates

Dating Stories

Thanks to Jenn Choi for asking my first question on Whale. Jenn asked about my funniest online dating story. Though I’ve been on 50 first dates or so, the number of dates that have a story worth telling are pretty small. Most of the dates have been pretty standard, although I’ve often wanted a date to throw up on me so I can have the killer dating story.

There was the time a date asked me if I was autistic. The worst part was that she was a special education teacher that worked daily with autistic high school students. In truth I wasn’t so offended and we’re still friends.

Once I went on a first date to an independent film festival that took place in people’s living rooms. The films were pretty funny. It was when I first started dating so I was somewhat awkward and for some reason didn’t my date to get a drink afterword. Because we were silently watching films the whole date we didn’t get to know one another and she had no reason to accept my second date invitation. Rookie mistake.

I’ve gone on a first date twice with the same person, though she didn’t remember our first date.

I’ve had my share of awkward dates where we sit on opposite sides of the table, sipping on our old fashioneds and staring awkwardly past one another.

Previously, I’ve written about a number of strange date cancellations I’ve received.

Perhaps the most interesting date experience I’ve had — and the one I discussed on Whale — is the time I went on a three-way date with a woman, let’s call her Bridget, and her boyfriend. This occurred because I had gotten myself somewhat involved with Bridget and she was in an open relationship. This was completely for the experience you must understand.

By this time Bridget and I had gone on probably three dates and she had sent me a questionnaire by email that required me to fill in my relationship and sexual history as well as my sexual preferences. However, before we became intimate she wanted me to meet her boyfriend. The three of us went to Thai food and then to bubble tea. Yes, it was awkward. Not the most awkward date I’ve been on though. We didn’t talk about the fact that I might one day soon become intimate with Bridget. I found it most awkward that they each paid for their own meal. Even with friends we often take turns paying I consider this ritual a display of friendship and intimacy. I can’t imagine splitting the bill with someone I’m dating.

Bridget and I dated for only another week or two and then, not wanting to actually be in an open relationship for the long run, I ended things and pursued another woman I had recently met. Like a handful of dates, Bridget and I are still friends.

Dating Tips

Here are a few tips and tricks I’ve learned from going on 50 first dates.

People Only Look as Good as Their Worst Photo
Maybe this is shallow, but people always ask. Perhaps this photo fact isn’t so surprising, people often put their best foot forward so almost by definition their photos are as good as they’re going to look. But listen we all look the way we look and shouldn’t be ashamed of it. And as we all know tastes in physical appearance vary widely. I think people should be confident enough in themselves to show what they really look like rather than trying to hide it. I’m 6’6″and in high school weighed a mere 150 pounds so you can imagine the teasing I was subjected to (even my basketball coach called me “sticks”). This self-consciousness has stuck with me a bit, but there I am in dating photos, chicken legs and all.

Occasionally someone comes out of left field and ends up looking much better than any of their photos. About 1 in 20 times someone will look so different from their photos that I wouldn’t know it was the same person.

Pay for the First Date (If You’re a Guy)
There is a common line of reasoning that says that whoever asked the other person out should pay for the date. Or that on a first date you should split the bill. It’s not 1950, but listen bro, just pay for the date. I’ve never not paid and I’ve never had a woman complain. I’ve had lots of female friends have guys not pay and they always complain.

I think most women appreciate this and chivalry isn’t dead. I keep this practice up until date three or four when eventually the woman begins insisting she will pay at which point I give in (after a while it become douchey to not let a woman pick up the check if she asks).

Create a Standard Date
If you’re going on a lot of first dates and are time constrained you really need to Mark-Zuckerberg-wearing-a-white-t-shirt-everyday your dates and just come up with something standard to do with everyone. Thoughtfulness is important, but on the first date you have no idea how you’ll get along so there is no sense in trying to come up with something creative. And trust me date planning can take a lot of you. Plus a large volume of creative first dates will leave you no first-time activities to share with your significant other once you do get serious.

I would also recommend making the date someone inexpensive as a matter of practicality. Going on 1-2 dates a week and spending $50+ each time can hit your wallet and feels even worse if the date is a dud.

Always do an activity if possible. Sitting across from one another eating dinner or finishing your drinks becomes very awkward if there is no chemistry and conversation subsides. An activity gets the blood flowing, loosens things up, and provides context for conversation. If you do get a drink try to sit at the bar side by side unless you are a skilled conversationalist. Make sure you are no positioned in front of a bar mirror. Even better, sit near a window where people watching can spark conversation and fill the silence.

I have two go-to dates. In the summer I buy my date froyo and we walk Greenlake in north Seattle. It’s beautiful and one of my favorite places to go anyway. In winter we play indoor bocce ball. I ask my date first of course and if they object I come up with an alternative.

These dates also offer an easy exit if things aren’t going well or the option for more fun if they are. Finishing a loop of Greenlake, for example, offers a natural break to part ways or a chance to walk across the street and grab food or coffee.

Second dates moving forward I try to do something fun and a little original.

Chemistry on an App Doesn’t Equal Chemistry in Real Life
It was somewhat surprising to me when I first discovered this, but it has held true. Often a date and I will banter back and forth over text, but when we meet in person the chemistry quickly fades. Other times the chemistry remains. Still other times answers over text are terse and I wonder if we should actually go through with the date, only to discover that in person we hit it off. Don’t rely too heavily on texting chemistry as measure of what the date will be like.


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