The time I accidentally went out with a homeless guy

There is really no easy way to start this story. Or to explain myself without coming out as the dumb one every time.

I am going to chalk this one up to bad judgment mixed with peer pressure.

I met this guy online. But pretty quickly after meeting him, I reconnected with this guy I've known for the better part of my life. He's the coolest. And I've been having fun chatting with him. 

And herein lies the problem. I can't balance. If there is a guy I am excited about - I can't go on dates with other guys. I can't. It is so difficult for me to keep an open mind that some other mystery guy I meet online could possibly be pretty cool, when I KNOW this other guy actually IS cool. So I just choose to hold out hope in my conversations with the one I know rather than exploring possibilities with strangers. To me that makes perfect sense, but not to all my friends. One more glitch, the cool guy lives in Illinois. And is pretty passionately against long distance relationships, so chatting is all this will ever be for quite a while. Hope is really all I have at this point. I would be holding out for quite a while for this one.

So my friends convinced me I needed to give the online mystery guy a chance.

In the midst of my internal battle on whether this was true or not, online man had sent me three emails trying to convince me to grab coffee with him. I decided (against my better judgement) he deserved points for persistance (stalking??) and what could the harm in ONE cup of coffee be?? (This might be a good point to interject that it is always good to listen to your gut. If you gut tells you that you probably don't want to go out with someone, you're probably right).

He drove to Pasadena to meet me. We had coffee. It wasn't great, but it wasn't torture. He loved to talk about himself, which was mostly fine because he's done lots of traveling and had some cool stories. I even let it slide when he talked over my stories or doubted it when I said I had done some trekking of my own in Nepal. Apparently I look weak.

But the best part was in the last 10 minutes of the date when he chimed in with this gem: "Oh, another interesting fact about myself, I live in my van!"

um...um....that's unique?

I guess it was nice of the guy to move to Pasadena for an hour an a half to have coffee with me. But I don't think there will be a second date.

I think holding out hope for Illinois is sounding better and better with each online date I go on....although, he did tell me his van had TWO beds in it! (not a joke, unfortunately).

"you are starting to become unrealistic in how bad you are at dating!" - Friend