First Dates

The First Date How-To

First of all: I am no dating guru. I’m just a girl who has been on a lot of dates. Anyways, here it is.

A girlfriend of mine recently decided to dip her toes into the pool of online dating and I could practically feel the shiver it put down her spine. Her apprehension mixed with her excitement cracked me up but she obviously wasn’t too hesitant because within a few days she had nailed down her first date. With D-Day (date-day, dur) drawing near, she texted me this morning minorly freaking out: What do I wear? How do I know it’s him? What if there’s nothing to talk about?

I literally laughed out loud but the truth is that when it comes to sitting down across from someone you have absolutely never met before, well, there’s a lot to think about. So here are my tips to surviving, if not enjoying, a first date with a stranger from the internet:

1. What to wear? Whatever you feel comfortable and confident in. As corny as it sounds, being yourself is the thing that matters most, and that includes how you look. This person knows nothing about you and if you genuinely are interested in the possibility of dating them, you want them to know exactly who you are. So wear something because you like it, not because it’s what you’re supposed to wear. Whatever that means.

2. How do you know it’s him? Well, how many people are sitting by themselves at a bar on Tuesday night looking like they’re waiting for someone they’ve never met before? You’ll know. This has literally never ever been a problem for me.

3. What to talk about? I joke that dating is actually just an exercise for my smalltalk skills, which is half joke, half true. You can’t gauge via online messages if someone is a great conversationalist or a dud, so you don’t know what you’re going to get until you sit down and say hi. Sometimes it’s easy and conversation is great. Sometimes it sucks but nothing makes it more awkward than sitting there silently thinking, this sucks. So smile and mention the weather and if he can’t pull it together, ask questions, smile a lot, and keep on going.

4. Most importantly, A first date with a man from the internet isn’t really a date. At least not for the first few hours. It’s literally a chance to sit down and see if you the other person has anything interesting to say and to feel out if there’s any potential chemistry. I’m a firm believer that chemistry is the key to a successful relationship but it’s not easy to come by. So hope for it but realize that if you had it with everyone, it wouldn’t be special. There are a lot of great guys out there but hold out for that spark.

I’m constantly reminded that my extreme willingness to drink and dine with the potentially dubious male population of Chicago is somewhat outside of the norm but I think if you take the right approach, it becomes a little more fun and a lot less awkward.


One thought on “The First Date How-To

  1. Pingback: Paid vs. Unpaid. An Unofficial Study | Diary of a Serial (First) Dater

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