- I was picked up over 30 min late.
- He had loaned his car to a friend and we drove in a small Nissan truck that I feared the flooring would fall out of at any minute, splattering us on the highway.
- He asked me at dinner how soon I hoped to get married and how many kids I wanted...Awkward!
- He took me for a walk to the roof of the city library after dinner even though I told him I really needed to get home.
- We got locked out. On the roof. The library closed. It started to snow.
- The officer that finally rescued us 30 minutes later kept suggesting we were "getting jiggy with it."
- When we got to his car, he'd parked in a no parking zone. The wheel was booted.
- When he opened the door of the car for me so that we could wait for the towing company, he shut the door on the heel of my $200 boots. It broke off.
- What the what?! After all that? He tried to kiss me at the door.
Happy Valentines Day!
And finally I have an awesome story of my own. This was embarrassing and awkward in one.
I used to work at TGIFridays as a hostess. One day in December, a new server named Rick started working there and I thought he was pretty cute. I came up with a master plan to get him to ask me out, as I did with my conniving manipulative ways bwahahaha! I would go to dinner at Fridays with a group of friends and have them 'meet me there' and go in before me, request to have Rick be their server. That way it would appear that they were just friends with him, and I could keep my dating life a little more private amongst my co-workers. I would casually walk in and then flirt with him the whole time he was serving us.
The plan backfired. My friends walked in and for some reason RICK himself was seating tables as well as serving and they walked right up to him and said "We want to sit in Rick's section." He said, "Um, I'm Rick." That was incredibly strange to him, I'm sure. But when I walked in and joined them, it all made sense to him and he smiled this giant smug smile at my not-so-smoothness. But he did ask me out. And the first date was very awkward.
You know how in movies they have those montages of people going into dressing rooms and coming out in all these funky outfits and upbeat music plays? I think that happens in every single Disney Channel Original Movie. That is what he was envisioning for our first date. He took me to the mall and MADE me try on outfits. It was. so. weird. We shopped around at some other places, including spending about an hour watching him find the perfect athletic shoe. He finally took me home and invited himself into my apartment. "I'm so tired..." I said, sitting down on the couch, hoping he would take the hint and go home. He sat down next to me and started kissing me all over my face. Seriously?! He's already jumping to kissing me. If anything made me put my guard up, its physical action before I'm ready. Finally I told him I had to get ready for work so he left, at last. Blech.
What was your most awkward first date? What was your best or worst Valentine's day? I'd love to hear in the comments!! Happy Awkward Valentines!Pin It