First Dates and Friendships

I must confess, the title is a bit misleading. I haven’t gone on any first dates (or dates in general) lately. But stick with me.

Have you ever noticed how similar the awkwardness of a first date and the awkwardness of the first time you hangout with a new person are?

Think about this with me.

A Prospective New Friendship/First Date:
* You meet a new person and you both decide to hangout together.
* So you two set up a coffee date, shopping date, lunch date, something date.
* You make sure you dress the way you want them to think about you.

“Can’t wear that sweater, too fashionable. Hipster is in … right?”
“Can’t wear that, too hipster. Don’t want it to look like I’m trying too hard.”
“I want to wear something that says, ‘I’m cool but I don’t have to work at being cool.’ Do I even own anything that says that about me?” – if you have to ask, the answer is “no”…

* You over analyze if you should be early, on time, or fashionably late.

“If I’m on time it looks like I’m too professional and I can’t step outside of my work life. Who wants to be friends with someone that is addicted to work?!”
“If I’m late, maybe that tells them I really don’t care, I had no plans, and I just needed something to do because I was bored… OR maybe it says I’m too busy to be on time to things and I won’t have time for them so they shouldn’t even bother.”

* You over analyze what to order and who pays or if you should go Dutch.
* Afterward, you leave and you begin over analyzing the time spent together. Every. Little. Thing.

“I had fun! That was great! Or did I have too much fun? Maybe I shouldn’t have had so much fun. I wonder if they had fun. I did, I had too much fun…”
“I asked way too many questions. They are going to think I’m doing an FBI background check… or worse, that I’m going to stalk them. Facebook stalking isn’t considered bad is it? Heavens, I hope not. I Facebook stalked them like a mother stalking her preteen son before today.”
“Oh no! I laughed way too much. They will think I can’t be serious.”
“WHY?! WHY did I tell the story about the time I threw up on a bus?!”

* You anticipate talking to them again but aren’t sure if you should wait three days before asking for a second round.

First Dates and first time hang outs with Prospective Friends are really the same thing. It is like an interview really. You want to know about their life without seeming creepy or like you are enlisting them for battle, but asking enough questions to seem genuinely interested. All while staying fully engaged in what the other person is saying.

Since moving abroad, I have had many of these Prospective Friendship Dates. Some good and have led to fun times, some a little more interesting than others and have led to straight up avoidance. I make no apologies for avoiding creepy guys (I consider any new guy I meet creepy until proven otherwise – still, no apologies). First Dates are awkward. First time hang outs for Prospect Friendships are equally as awkward. But, the saying is true in both cases, “you never know until you try”**.

**Disclaimer, the saying “if at first you don’t succeed, try, try again” does not necessarily apply here. For an explanation, see First Date Fails

Remember, you are not alone in your awkwardness. We all experience it. If anyone tells you different, they are lying and must have an embarrassingly awkward story to go with that lie.


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