Alright, so full disclosure; I've had a bad week. I'd asked out friend's sister-in-law, it apparently became a whole situation where her entire family were talking about it, highly embarassing. Then Monday morning, I got fired. So yeah, my self-esteem is pretty low now.

But I guess now that everything has crumbled apart, it's really made it impossible for me to make any excuses; I am the biggest problem in my life. I've just become this super unhappy dude, and at 36 years old, my life has already passed me by. I need to make some fundamental changes to who I am as a person, and really figure how "who I am, and who I want to be".

I've become really reserved as I've gotten older (I suppose I've always been shy), but on the rare occasion I actually drink (enough to get tipsy or bordering on drunk), I think I become a lot more fun. I think I become "the real me", in a sense; more playful, less bogged down by stuff going on in my life.

But a perfect case in point, there's a woman at work that seemed attractive. I sent out a couple of emails to coworkers yesterday, just saying it was a pleasure working with them, stuff like that. But with her, I added "Here's my number if you ever want to reach out and pick my brain about digital marketing, or grab coffee sometime". (I mean, I got fired anyways, what's the harm now?). And she responded "Yeah I'd like to keep in touch, here's my cell, reach out any time".

Probably platonic, but hey, maybe not? But even if there was/is an interest, I don't even really know what to talk about if I invited her out to coffee. Obviously not work (because that could easily turn into a bitch-fest), I don't really know anything about her (other than I think she said she has dogs), what kind of conversations do you have or questions to ask, that aren't just "interview questions" (as someone said in another thread).

Hell, I'm really not in the head space to be "dating" anyways, but I feel like if there is an opportunity with that woman from work, I've gotta take it, right?