Hey, instead of self wallowing... why not enjoy being single instead? Change your perspective for now, then switch back when you are more financially stable.
Don't get cougars. What I meant was to wait a few more years or move to another location. Thus you need the money.
This. It seems from your comments that you already have this view that "everyone but you is hooking up."
Someone once told me a long time ago that "women will always be there."
Concentrate on just being the best "you" that you can be. It probably sounds cheezy but it is very liberating. The advice I give is compare yourself and compare her to you, do you have the same interests, does she measure up in your eyes that you guys are even on the same level, circle of friends, etc. It sounds like more of a crush than trying to go into an actual relationship.
Check out a couple of books I think that would help you: (again I know it sounds cheezy but trust me on this one, what do you have to lose)
"The Game" by Neil Strauss
"The Mystery Method" by Mystery
I used to be I guess what was considered a "nerd" all through high school. Of course I didn't think so, but I liked video games, had a odd group of friends, and pro wrestling. I wasn't considered a ugly guy by any means, but to all the super hot females that I was crushing on, I was always that "your not my type" or "friend-category" dude. And I also didn't notice really well if a woman was into me.
I had my share of awesome hook-ups though, much to my satisfaction and entertainment after high school and college and the military.
But everything was wayy easier when I flipped the script mentally and was just like fuck it if they like me then awesome if not that's awesome too, and I moved on.
Hell, I remember jocks (who I were cool with) in school telling me that I could hook up with some super hot girls if I had "game." (Whatever that meant at the time.)
If she kissed you and said your cute, then fuck yeah. If it doesn't go further than that then treasure that moment privately with yourself that hell, you can't be that bad if that happened and move on. Hell, one or more of her friends are probably into you and you don't know it. (Girls talk obviously..)
Just don't mind fuck yourself about the situation. Invite her (and only her) out to eat or movies or something and talk exactly about what happened and if she want's a relationship. Don't be nervous just through it all out there and see what happens. At least then you will have that moment to yourself too. If it happens it happens if not, don't harp on it (I know it's probably hard) but there is always someone better. Like I mentioned
women will always be thereAnd just so you know I still like video games, have my friends from high school, and pro wrestling. Also I been together with my wife for 6 years now.
Oh yeah, you are in your twenties stay the hell away from cougars. Unless of course their willing to splurge money on you....lol
Definitely check those books out. The read will do you good.