New Territory

So I’m having to learn how to put myself out there and ask guys out… What is this? 

I don’t know what to say. I don’t like the feeling of being able to be shot down. I don’t like having to make the first move. Is this what guys think about? Are they this contemplative? Do they overthink it like I’m overthinking it?

I started Facebook messaging (so old school and lame) this guy I know from my gym trying to give him an opportunity to ask me out because he’s always a little flirty with me when he sees me. He didn’t take the bait but I’m not sure if it’s because he’s not getting it or is shy.

So in come the messages to my girlfriends. The screenshots. The questions. The overthinking. “Do I just ask him myself? Do you think he’s interested? What if I get shot down? What the fuck am I doing? What should I say that’s cool but not creepy?” Fuck.

I guess I’ll ask him out. 


First up to bat: Peter

Oh Peter. You had so much potential. Peter (name changed) was one of my first matches on Coffee Meets Bagel and sounded like a great catch! An attorney, educated, cute and an interesting profile. I was stoked we had a match.

Peter seemed pretty funny and witty through text and made me laugh out loud a couple of times but was slow to set anything up with me even though I told him I was interested in meeting up. After 4 days he finally asks if I’m up for coffee or a drink so we agree to meet at a local bar for drinks. In this case, drink.

We meet up and it was awkward from the start. He went for a hug. I went for a handshake. Once we sat down he was reluctant to open a tab and made it kind of awkward. He eventually gave a card for our beers. I should have just given her a card for my own but I didn’t know how much more awkward we could take in such little time.

I’m really good at not being awkward and talking about things that are light hearted, maybe a funny personal story , a disaster date story. Anything to just lighten the mood and have someone loosen up. Peter did not loosen up. I’ve never been made to feel so uncomfortable in my life. He would stare at me or into the distance after I said something and didn’t know how to keep a conversation going or really have anything interesting to add to anything. He also tried to ask me about why my last boyfriend and I broke up and what happened there and how I met him? Nooooo. That’s not something people wanna talk about when first meeting somebody.

The first thing he asked me is if I had any tattoos and then went on to insult women with tattoos. Everyone is entitled to their opinion but it felt mean spirited. He also admitted that he’s conservative and isn’t really a fan of the scene in Austin…. I love Austin! And I love exploring this city and the people I know and have met are great people.

It was obvious Peter and I were not a match and he never lightened up the entire time. Even when we found something in common, he didn’t try to keep the convo going or ask questions.

There’s two sides to every story. Maybe I wasn’t conservative enough for him or maybe he didn’t like how I talked or felt I talked too much. I dunno. I just tried to make it the least awkward I could until we got through our beers and I could leave.

Afterwards I swung by a bar I go to regularly and had a reward drink (ok, drinks!) and dessert for surviving the date. I’m thinking about making this a regular thing.

Diving into Dating

I am 25 years old and for the first time in my 20s I have an opportunity to explore the dating scene and all of it’s madness. Currently I am not looking to find “the one” or a very serious boyfriend, but I am up for meeting new people and hopefully will document some great tales, good and bad.

 I have downloaded two dating apps, coffee meets bagel and tinder. I have also been going out more often and meeting men through mutual friends. After being in two consecutive long term relationships, it’s been nice putting myself out there and observing the responses I get from men. I’ve realized I’m pretty awesome and my self-esteem has definitely improved. I may not be everybody’s cup of tea though, but my appeal is high enough where I’m able to set up dates very easily and will do so to document some life experiences and learn more about the singles scene here in Austin.
Let’s do this!