The First Date: How to Enjoy Yourself — Before, During, and After

DeQuaina Washington
5 min readFeb 20, 2020

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Photo by Waldemar Brandt on Unsplash

We’ve all been there: staring at the phone waiting for the text that will affirm that we effectively seduced the date from last night. Replaying every moment in our heads to see where we made the mistake that dashed us from consideration if that text doesn’t come. Mulling over the bad jokes we told or what our date thought of us when we sent that entree back to the kitchen because it smelled “off”.

All of it boils down to ruminating about where you went wrong, and that’s no fun. It makes sense that we do this, however. The act of dating requires an uncomfortable level of vulnerability — especially at first meeting.

It’s a treacherous audition where every detail of your person is served up for judgement. There’s no escaping that fact, but there’s power in learning to turn the delicious pain of forging a romantic connection into the sweetest pleasure — and feeling good about yourself even if a connection fails to form.

Go into your first date with the right mindset.

If you’re not excited about your upcoming date, cancel it. You should be dating as an act of self-love: you love yourself, and now you’re finding someone else to love you, too. If that’s not the reason you’re donning your best threads and braving the unknown, you should examine the reasons you’re going out on the date in the first place.

If any of those reasons involve what someone else thinks you should be doing, pump the brakes. You don’t have to date. You’re undoubtedly pretty awesome on your own, another person should only complement the amazing things you already have going for yourself, not create them.

It’s important to respect your date’s mission and their time. They WILL notice if you’re in a funk or, if you’re — even subconsciously — treating them like you’re doing them a favor. News flash: the first date is a mutually beneficial act, your time and effort is of just as much value as theirs. If you’re not ready to lend them your time with a clear mind and a positive outlook, save the date for a time when you can offer just that.

If nerves are the reason you’re feeling trepidation, lean into the uncertainty. It’s normal to feel nervous, and to be honest, that’s part of the fun. You have no idea how the night will go, and that means that it’s an adventure!

Practice pleasurable pre-first date prep.

Photo by Toa Heftiba on Unsplash

Treat yourself! Pamper yourself! This is a brave, fun thing you’re doing. Act like it. Ply yourself with some intense self-care beforehand. Get that haircut you’ve been putting off. Polish your nails or go get a manicure. Wear that super flattering dress with the tags still on it. This is the time to present the best of yourself — this doesn’t mean you should do something you never do (like wearing fire-engine-red lipstick when you usually go with neutrals) because you do want to feel as comfortable as possible.

Be you, but be the best, most well-groomed version of you. And shoot, if you’ve been waiting on a date to wear that button-up with the loud plaid print you can never find an occasion to wear, do it. If they don’t like it then, really, is that person worthy of a second date?

Find comfort in the fact that you’re both judging each other.

Because truly, that’s the point. If you go into a date without that in mind, you’re setting yourself up for the scenarios I mentioned at the beginning.

Keep in mind that no one is their real selves on the first date, not entirely. It’s not that they’re a different person, they’re just an abridged version — which makes sense as a date is finite and every facet of the complex human psyche will not be tapped in two hours over spinach artichoke dip. This fact will remove some of the pressure you feel to make an accurate assessment of who they are in such a limited amount of time.

If you don’t like their shirt, that’s fine. If you think they talk too much or if they pick over their food or if they’re rude to the waiter, make a mental note. Trust your visceral reactions to these things. They’re keeping a mental list as well that they will review in real-time or when they’re alone, and that’s normal.

The key is determining what’s important to you about the person you’re looking to spend more time with. If bad clothes aren’t a deal breaker, remove that thought from consideration. If you don’t agree with their philosophy about raising children or they drop one too many ill-placed F-bombs, then maybe your rendezvous was a one time thing. Keep in mind, those assessments are being made about you as well, and you might not make the cut. It’s all par for the course and is not a reason to feel bad about yourself afterwards.

The date crashed and burned. Now what?

Back to the drawing board, that’s what. Who cares if it went badly? First of all, you just met this person. You shouldn’t be that invested in their opinion of you. Sure, you want to put the best foot forward during the date and you most certainly should, but if your best foot steps in a mound of your date’s raw emotional baggage and torpedoes that whole thing — that’s not your fault. That’s just the reality of meeting a new person who brings a whole set of experiences — and triggers — with them.

Besides, if you’re dating multiple people, as you should be, you’ll have other people to distract you from obsessing over the steaming pile that date became.

Don’t take it so seriously, your date is, essentially, a stranger.

Your date’s opinion of you is just that, their opinion. They can’t possible really know the entirety of you in the short time you’ll spend together, so relax and be yourself and let the chips fall.

The thing I think some people forget about dating is that it’s a numbers game. It might take multiple dates with different people (or, even with the same person) to make the connection you’re seeking. When I was in the dating game, I never assumed that I was going on a date with “the one” or even “one of the ones”. I went in with an open mind and a mission to enjoy myself.

It’s incredibly fun to meet new romantic prospects and learn what makes them tick while you decide whether you like their teeth or appreciate their interest in rock climbing. I met some of the most interesting people ever on dates, and we didn’t always go on a second date, and that was okay. Enjoy the journey, and everything will be okay, you prize, you.

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DeQuaina Washington
DeQuaina Washington

Written by DeQuaina Washington

DeQuaina knows stuff about hiring & people strategy, relationships, video games, and sci-fi, so that’s what she writes about! Visit me: www.prosepunk.com!

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