Background on me: I'm 37. My ex-wife and I started dating when I was 17. We got married after we graduated college and eventually had three kids. In 2009 she had the first of a number of breakdowns/mental breaks and ended up leaving me and the kids in Jan. 2010; I filed for divorce in October, and it was finalized in Feb. 2011. Since then I've dated two women...one a handful of times, the other just one date.

I have never been good at dating. Actually, no, that's wrong. I'm good at dating. I'm HORRIBLE at everything that leads up to a first date. More often than not I end up talking myself out of asking someone out because I end up playing the whole relationship out in my head, and it always ends.

A while back, while talking with a co-worker I've always found attractive, I noticed she was no longer wearing a wedding ring. I didn't bring it up, though, because we weren't THAT close. She's very friendly and easy to talk with, we've done some after-hours co-worker group outings, and we're Facebook friends, but that's the extent of our friendship. So I bumped up my strolls to her side of the building to once or twice a week. A couple of weeks ago, while talking about a new job prospect she had, she mentioned that she was divorced. I don't know how recent it was, but I got the feeling it hadn't been final for too long.

So, she got the job and put in her notice. Also, a close relative died. So she's been BUSY the past couple of weeks.

I said "screw it" to my insecurities and decided to ask her out. I thought she was worth any initial anxiety in the hopes that this might actually turn into a relationship. She said yes! Woo hoo! But with her starting a new job, she's busy and we haven't been able to set a first date yet. So I'm over here stressing out that she only said yes because she's just a nice person and she'll back out before we can make plans.

We've texted a bit, but I don't want to be pushy or bombard her. I'm hoping we can set something up within the next week, because really all I want to do is get the first date underway. Regardless of how that ends, it will have happened, and I'll never have to wonder "What if?". But right now, I'm kind of a wreck.

TL;DR - Single father with insecurity issues feels like I'm mentally sabotaging my first date with a wonderful woman before we've even gone out