This happens a lot less than you might think. A flirt I may be, but with boys I most certainly do not. Let’s go over my last two “oops” moments.

The First Boy

The first was at a Robyn concert. There – right there – proof this was not my fault. We had drank considerably before leaving so I promised myself no drinks at the concert. Of course we go to the bar right away and I run into an old friend, aka an excuse for a shot.

While on our mission to find people with lower level general admission to sneak us in and save us from the possible dangers of being drunk and dancing on the balcony, I ran into a boy with a Britney Spears Femme Fatal t-shirt on. I immediately assume he’s gay and therefore my new BFF.

He buys me another drink, my third at this point, and I chat him up trying to see if he can sneak me and my three friends into the lower level. Turns out he can’t and I run off to find my next target.

We got in. We danced (oh we danced!). It was awesome.

After the concert, while waiting for a cab outside, Britney Spears boy comes up to me. He tells me we should hang out sometime and asks for my phone number. Of course I think nothing of this because he’s a boy WEARING A FEMME FATAL TOUR T-SHIRT AT A ROBYN CONCERT. Color me nothing short of shocked when he starts to pull me in next to him and whisper sweet nothings in my ear. Whoa.

Luckily, our cab had arrived and my friend Anna pulls me from his grasp. He starts texting me immediately. The other members of our cab ride home were in disbelief. No way was this guy straight. They convince me to text him back and ask him if he’d be interested in a threesome with my two guy friends (gay) who I was with. Yeah because that is a better idea than “I’m sorry, I’m super gay. Thanks but no thanks.” Clearly, I’m a genius.

He responds that he’d only be interested if I was there. Then, as if to convince me, sends me a picture of him with his tongue out. I kid you not. I wish I still had this grotesque long tongued man’s photo. The one to the right will have to suffice. Even though his tongue is out, it’s not as frightening as the one he sent me. I promise.

The Second Boy

This instance might be slightly more my fault. I go to trivia night every Wednesday night. Normally we go and have a few drinks and win or come in second and then leave. One Wednesday, we got real rowdy. In these instances, many people go into flirtation mode. Surprisingly, this time, not me.

My gay friend spotted a man in a nice sweater across the room and wonders aloud if he’s gay. Armed with liquid steel armor, I immediately approach him and his friend and start chatting. I know almost instantly sweater guy isn’t gay. There was something in his manner of talking and carrying himself.

Sweater man wanders off leaving me with his friend. Turns out his friend is a bartender there on the weekend. I learn his name but instantly forget it. I finally get to my point and tell him I had approached them on a mission to find out of sweater boy was gay. Bartender tells me he is, indeed, straight but “he gets that a lot.” Ha. I leave to go take another shot. Naturally.

I return the next week and bartender comes up to our table and hugs me. Me, not knowing his name at all slash barely recognizing him (I’m not good with names or faces), try to maintain composure and not let on that I am clueless at this point. I finally put two and two together and greet him with a smile. Too late. He definitely knows and has walked away. Oh well. If only it ended there…

Instead, as I’m about to leave, he comes up and attempts a conversation again. Somehow it gets brought up that I just went back to my high school for my alumni improv show. Turns out bartender is a part of a community improv troupe low on females and he asks me if I’d be interested in joining. I give him a solid maybe and he asks for my phone number so that he can give me the details.

I wake up to a “hey pretty lady” text message promising to call me later that day. He does and tells me he was going to invite me to an improv show at Unexpected Productions but they no longer do Thursday night shows. I thank him but tell him I have plans anyways. The following week, on trivia night, he asks me if he “gets” to see me later that night. Luckily for us both, I also had plans that night. His final text last week read: “I’m super busy until February but I really want to go out with you as soon as the stars align ;)”

Woof.

I really need to learn how to break the “I’m gay” into the conversation. Any advice? At this point, I just want to bring my cute, single, straight girl friends to the bar with me next Wednesday and subtly throw one in his direction. He seems nice enough.

If only I was this good at flirting with lesbians….