What is the most awkward date you’ve been on?

Questions asked and answered for my daughters

Shaun Holloway
Lessons from Ordinary
3 min readMar 6, 2021

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Driving. And Driving. And Driving.

What a great and awkward question! But, it’s definitely a fun one to ask. I haven’t been on too many dates… you could say I was picky. Yes, let’s go with that ;-), and there is one that tops the list of awkwardness.

I was in high school, and I went to church youth group where this girl asked me to go to homecoming with her. We didn’t go to the same school, i.e. different school districts. Of course, I said I would go, because who would turn down a girl asking you to go to a school dance!

I was all ready to go. Got the corsage flower thing. Dressed nice. My car started and stayed running when it was supposed to. All set.

I picked her up, and the traditional activity to do first is dinner before the dance. So, we drove into the city, and silly me, I didn’t make any plans on a location, as I left the choice up to her. Nothing sounded good to her. So, we drove some more.

At this point, I should have become suspicious of her motive. But, I was clueless and didn’t know any better at the time.

Then, she said something along the lines of, “Let’s go ahead and go the dance.” Um, alright.

TO THE DANCE

We arrived… she was dressed in this blue sequin dress that hugged her, and we got our pictures taken under the fancy arch thing.

The dance floor was encircled by classroom chairs, and the decorations were the typical streamers, glitter everything, and some music. Remember, this is not my school. The only people I knew were the ones that also attended the same church group, and none of them were there yet or would not be there at all.

She went to talk to her friends, as I sat in one of the classroom chairs… she didn’t invite me to come with or have me walk over with her. It didn’t help that at the time, my confidence wasn’t very good either, so I wasn’t brave enough to insert myself into a situation with people I didn’t know, let alone do so in a strange place.

I sat and watched them talk, and it was still early in the evening. Not everyone was there yet.

I don’t know how long I sat there. I didn’t interact with anyone, but I remember it felt like a long time. Talk about awkward. My “date” was hanging out with her friends, and she didn’t intend to have me even close or want me anywhere near her friends.

She finally came over to me and said…

“You can go home now.”

What?! She was going to hang out with her friends and have them take her home. I was too shocked about the whole situation to be upset or tell her off in some smart way.

What was I supposed to do? She didn’t want me there, and all she needed was someone to take her to the dance, so she didn’t have to go alone. She used my presence to ease her embarrassment of not having a date to the dance, and ultimately, she hurt my feelings.

I wasted gas in my car, money on the flower thing, and didn’t even get dinner. I was played.

AFTERWARDS

So, you may be wondering what happened at the next church group meetup? Well, the answer is… nothing. No talking; complete avoidance. Awkward. I sure wasn’t going to “fight for her,” because that’s an insane thing to do for someone like that.

I did get the pictures from the evening though. The ones taken under the archway. She handed them to me… probably all of them. What did I do with the photos? I burned them. Yep… in the garage, matches, lit them up, and watched them burn.

This is one of those stories that I look back on and think… if I was the person I am today back then, it would have been so much better… or at least I would have known better and took the high ground by exiting the situation before anyone got hurt.

Girls… as you grow up, you will have the opportunity to meet many people. Remember… be kind to the nice, quiet, geeky guys.

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Shaun Holloway
Lessons from Ordinary

Lessons from Ordinary. Business and life learning from everyday objects and common questions. http://www.srholloway.com