Guest Post | How to Have an Awkward First Date, by Brooklyn Jolley

Last updated on 29 December 2024

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Ever want to know how to have an awkward first date?

Hopefully not! But Brooklyn is here today to share some of the things that she’s experienced so we know exactly how to have an awkward first date (or not, as the case actually is).

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I know I know, ANOTHER Guest Post. But don’t stop reading. Because if you need a laugh today (and believe me you do) I am your girl. I am here to share all the glorious horrible awkward dating experiences I have had in my life. Yep. You’re welcome.

So I wrote a list for all the men in the world to follow if they want to know how to have an awkward first date.

1. Show up 30+ minutes early

Half curled hair, no shaved legs, eyeliner on one eye, this is what we girls live for. Being picked up super early. Always a great start to the night.

2. Don’t open any doors!

Not the car, the restaurant, nothing. Standing outside a door waiting for her to open ensures awkwardness.

3. Ask her zero questions about herself

Make sure you are terrible at making conversation. Don’t ask her what she likes to do, about her family, or where she is from. All of those would lead to actual conversation. And that would be a pity if you are aiming for awkward.

4. On the same note, talk about yourself the whole night

I’m not talking about answering the questions she asks and telling stories at appropriate times, those are all comfortable. I’m saying you should act like a total tool and tell her all about your gym buddies, your high school glory days, and the newest addition to your hunting wall. Frat party stories are extra credit.

5. Bring up other guys you know she’s dated. Ask how they are doing

No explanation needed.

6. Talk about politics, lawsuits and rumors you’ve heard about her past dating experiences

The best way to bring out the crazy in a girl is to get her on the defense about the things she really believes in.

7. Try to kiss her in front of her parents

This is especially valid in high school.

8. Don’t give her any clue as to what you are doing or what she should dress like

Nothing creates awkwardness as well as showing up for a hike and picnic in a white dress and heels. Nothing.

9. Invite yourself in when you go to drop her off

Even if you thought things were going well, you wouldn’t want to just say goodnight and leave her wanting more would you? Didn’t think so. Overstay your welcome until she has to come up with an excuse to bail.

10. Ask her if things feel awkward

Because well if they didn’t, they do now.

Have you had an awkward first date? Let us know below!