Tell Us about Your Most Awkward Date Ever

All my fault.

Met this girl while traveling in another country. We’re in a bar chatting and hitting it off. I mentioned that I live in Los Angeles and she tells me that she’s moving to LA after her trip. Cool… we become Facebook friends so that we can keep in touch and hang out once she moves to LA.

Fast forward a couple months later and she’s now living in LA. We had been keeping in touch through messenger, chatting and flirting. She makes a Facebook post that the documentary Inside Job is playing and that she’s gonna go watch it that weekend and “get mad!” (the movie is about the 2008 financial crisis.)

I reply to her post “I’ll go get mad with you!”

So we message and call each other and make plans to meet Saturday evening at a theater on Sunset Blvd in Hollywood for the 7 pm showing.

Now here’s where my fuck up begins… it didn’t cross my mind that this was a date. Even though we had hit it off when we met, exchanged contact info, had been flirty messaging each other the last couple months, and had now made plans to get together on a Saturday night … no, for some reason “date” hadn’t crossed my clueless mind.

Saturday night – I’m outside the theater by the ticket booth waiting for her to arrive. I had only seen her in person once before while travelling and that was a jeans, t-shirt and flip-flops kind of situation. Suddenly she appears … hair down, makeup on, dressed all in black with a black mini skirt, black stocking and high heels! I think, “DAMN!” She looks good! She really dresses up for the movies!”

Me? Still clueless that this is a date.

We stand in the ticket line talking, moving up the queue until we hear “Next, please.” I look at the ticket guy, he looks at me, I look at her, she looks at me, I look back at the ticket guy and am confused why the situation suddenly became awkward. I think “OK, nobody is reacting here, I need to take charge of this situation.” And being the gentleman that I am, I look at her, think “ladies first” and with a wave of the hand I tell her “Go ahead, buy your ticket.” The guy in the ticket booth looks at me again, I look at him and then back at her, with an awkward pause and stutter she says “O...OK” and buys her movie ticket.

Me? Still clueless that this is a date.

I step up to the ticket booth window “One ticket for the same….” …. FUUUUUUuuuuuuccccCCCCKKKK! The flirty messaging, Saturday night plans, her with hair down, makeup on, dressed all in black with a black mini skirt, black stocking and high heels! THIS IS A DATE!

Me? Panic mode.

I consider myself a feminist and am completely fine if a woman wants to pay for herself. But it’s not even close to how this situation just went down. First date and not only didn’t I even offer to pay for her measly movie ticket, I actually waved her off and TOLD her to buy her own. OK, think, how am I going to salvage this DATE? I know, I’ll buy her all the popcorn, candy, and drinks she can handle! She can order all she wants, all on me. “No, thanks, I don’t want anything.” DAMMIT!

We enter the completely empty theater about 25 minutes early… 25 excruciatingly long minutes. Lights on, no previews playing, just the two of us sitting alone in ear buzzing silence. The easy flowing conversation we had going while standing in the ticket line was gone. I’m racking my brain trying to think of something to say, something amazing that will rescue the both of us from this abyss of awkwardness… nothing. But, she does tell me that because she just moved here she hadn’t bought a car yet so she had to take the bus to the theater. Yes, to get to this date she had to walk to the bus stop, pay for the bus, take a 30-minute bus ride, then walk to the theater… with her hair down, makeup on, dressed all in black with a black mini skirt, black stocking and high heels! I’m an ass.

The movie starts and provides sweet relief from the silent awkwardness but I couldn’t concentrate on the movie, I’m too busy formulating a plan for redemption. I got it!

Movie ends.

We get out of the theater and it’s still early, only 8:45 pm. Perfect. It’s Saturday night, we’re in Hollywood on Sunset, we’ll go out, hit up a few bars and I’ll show her a good time… “Hey, let’s go grab a drink!” I’ll even pay for the drinks

/r/OkCupid Thread