Some of the Most Awkward Dating Stories

By Tamás Ő. — Verified by Sander D. — Last updated: July 31, 2024 — (0)

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People make silly mistakes all the time, but when doing it before a stranger you wish to woo over, the awkwardness level may rise sky-high. Dates can turn into a scene of an awful sitcom even if you are up in your game. Still, it can be educational to read about these flub-ups (or at least you won’t feel so bad when something similar happens to you). We’ve gathered some brutally honest and true stories from Reddit, and added our own thoughts to them.

“I thought it was just hanging out, and she thought it was a date. In my defense … She brought her brother. Then later she got mad at me for not making a move.”

Even though people agree to go out together, the exact purpose of the meeting is often shrouded in mystery. While one assumes that it’s a date, the other believes it’s just a simple dinner and nothing else. A trivial detail, but it strictly limits whether you can make a move or not. Taking the initiative makes a girl shy away if she’s not ready to establish a relationship, but as our example shows, the other scenario is just as awkward.

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“We talked about avocados for an hour because it was the only thing we had in common.”

Running out of topics to discuss is the second worst thing that could happen on a date (the first one is setting the restaurant on fire with the candles). To avoid long, uncomfortable silences, prepare some interesting stories or jokes in advance. Also, pay attention to what your partner says to ask them more about something they told.

“He took me to Arby's.”

A short, but quite self-explaining story. The morale is: first impressions do matter, so take your partner to a classy place to eat. If you don’t know any restaurant that could fit the evening then resort to asking your friends for good places or rely on Tripadvisor’s best picks for romantic get-togethers.

“I went to the movies with this guy my friend set me up with – we saw The Girl with the Dragon Tattoo. Nothing like sitting next to an almost-stranger watching anal rape scenes.”

As we mentioned, making an action plan before the date can really pay off. This is especially true when it comes to movies. Act against your first instinct, and avoid movie theaters! You cannot see each other in the dark, not to mention you focus on the action instead of your partner. You can spend that half an hour with quality events instead. Or at least choose a romantic film.

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