Saturday night

Wow. What a night. What started with so much promise and excitement, came screeching to a whiplashing, breath-stealing halt in just over three seconds.

I started seeing this woman two weeks ago and we had two really fun and promising dates. Our communication was spot on. The conversation flowed so easily and readily. We talked about fun future date plans. We talked about serious and exciting future life plans. She wanted to move back East like me and was already growing tired of the Colorado lifestyle, much like myself. We were snarky and cynical about the same things, wading in deep into serious local and world issues. Serious turned on a dime and we were giving each other shit about something ridiculous we learned about the other, which only drove the attraction. All of this to say, we hit it off quickly and hard.

Then, on our third date, while talking about something totally innocuous, I asked her if she was looking to get married in the nearish future and she said yes. A second of hope dangled so freely in the air, ready to be seized upon, only to be snatched away two seconds later, with the admission that she didn’t think she wanted kids. Fuck.

We both knew immediately what just happened. There was nothing that could be done to undo it. Her words hung like a cloud in the tavern. Neither of us knew what to say. Both saddened in a very real way, which was equally alarming. She slipped off to the bathroom, later admitting to crying just a little. I sat there dumbfounded, numbed way more by the last minute than either of my drinks. This is not how Saturday night was supposed to go.

We decided there was no need to continue the rest of the night. On the car ride back to her place, we tried to bargain away the last thirty minutes, unsure whether either of us could meet the other’s needs. That car ride was such a visceral and unpleasant experience, and was unlike anything I’d really felt. Thanks for the experience I guess…

We pulled up to her house and I started to walk her to her door, when we both decided to at least test the real chemistry for the first time, just to see. Such a bad idea. It was beyond fabulous. We stood there locked together for a minute, savoring what was sure to be our first and only romantic moment. At the end of it, I whispered ‘goodnight’, only to followed by a more serious ‘goodbye’ that rung so true.

Such a dramatic entry for such a seemingly small encounter. But sometimes you have a gut feeling about these things and this was one of them. We’ll both be fine, but right now I don’t care about that. I just want our Saturday night back. I want to continue to plan a camping trip. I want to think about where to move back East. I want a second, third, fourth kiss and beyond.

Dating sucks.

If it’s me reading the signs.

Geez, where to begin?

I had a pretty odd date experience the other night. We had been talking for about two weeks. We seemed to have a lot in common and our texting conversations were pretty easy going, so we were both excited to finally meet in person. Our initial plans changed at the last minute due to somewhat unforseen circumstances with a ceremony in Old Town and a billion people cramping our style. Our alternate plans were ok, but nothing special. And to be honest, I was already a bit bummed our original plans fell through.

Our conversation never really got to the point of easy and kind of felt like a struggle at times. I’m not sure if she was shy/nervous or if I was giving off a weird vibe, but nothing really clicked. The night honestly had a constant feel of a ‘Curb Your Enthusiasm’ episode where you’re just slightly uncomfortable at all times, but not to the point of bailing.

Anyways, after dinner and a drink, we walked back to my truck and I asked if I could drop her off at her house and she politely declined and said she was fine biking home, in the cold… Well, to me, that’s a pretty clear coup de grace on the night, so we hugged and parted ways. No big deal. Until I got home and she texted that she was confused by my body language and couldn’t gauge my interest and said she wished I would have kissed her goodnight. What?!


Someone please explain this one to me. I’m waving the white flag because I honestly have no clue what I’m doing anymore when it comes to dating. Sometimes I pick up good vibes that apparently aren’t there and other times I feel like things are d.o.a when that’s not the case at all. All I know, it’s pretty dejecting, and really, more importantly, confusing. This shouldn’t be this difficult.

This is partly why I haven’t dated at all in the last couple of months. I’m tired of the negative feelings I get from dating and honestly, I don’t think I align very well with the people of Colorado and their lifestyle. I sometimes wonder if it would be this difficult in other parts of the country or if geography has nothing to do with it and it’s really just an indictment on my generation, or even worse, me.

Anyways, just thought I’d give you the other side of social media. We all complain that social media is a filter for only what’s good in someone’s life. Here’s the other side. This is the struggle that few put on display, in all it’s glory. Stay tuned for the next episode of ‘Jacob Has No Clue How to Date’.