Ehh, allow me to rant a bit in here, take a bit of steam off...
I was in a dead-end relationship for a year and a half. My girlfriend was very tomboyish (not really a problem, but it is when she doesn't even bother to dress up for friend's parties, or refuses to go to weddings because she'd need to wear a dress), and would get all pissed at me when I would tell her that she needs to put some more effort into herself. She was in her own comfort zone, never wanting to help herself or her situation (living at home with a crazy family, whose problems she always took on her shoulder)... worked a dead-end job, never had any cash (was a bad saver, spending all her money on her nieces), didn't want to go back to college for her Masters, didn't even have a car... not to mention I never really felt like she took any interest in myself or any of my interests (she didn't even bother listen to some of my DJ mixes!) So I told her I didn't see things working out and that we should "take a break". Then after a few days on break, and taking my relationship status off of Facebook, she called me yelling at me that I was an asshole for doing that and that she never wanted to talk to me again. I was real sad, because as wrong as the girl was for me, I still deeply cared for her and wanted to see her pull herself out of her situation. Even after all the encouraging I tried to do. She was a quitter and loved to make excuses.
During the relationship, I built up my confidence a whole ton, something I've always suffered with all my life (I'm now almost 30 - and have had plenty of girlfriends, but there was always a lingering sense of self-doubt I had). Bought a new house and finally getting ready to live on my own, getting rid of some people who were holding me back, working extra hard at my job (where in recent years I've kinda been a slacker)...
So fast forward to last fall... I started up OKCupid again, with renewed confidence. I've been going on lots of dates, with girls who have much more going for them than my ex. But it hasn't been working out yet. I hardly ever get second dates with the girls, and have only met one girl I really clicked with -
I do the simple first dates - meet for coffee, or at a small pub for a drink. And then an activity date for a second... if I can get that far!
Anyways, 2 things have popped up that I have some questions about:
-what do you guys do to try and get a followup? You had a first date that didn't end in disaster, and liked the girl enough to want a second... how do you go about getting that second date? I usually will call back and be like "Hey, what's up? I had a nice time the other night and wanted to see if you want to go out again.."
-Also I went out with a really cute girl a few days ago, she was a bit on the younger side (22) but very pretty. Seemed to have a good time, we went out for drinks and I did a bit of kino (playful touches), maintained eye contact, body language (this is the only thing I'm a natural at, being Italian and all), etc. Called her up, got voicemail, left a message... and she texted me back with "I had a great time too! But I think we are better off as friends." Should I even bother writing back at this point? Something to the extent of "OK, well friends hook each other up, do you have any single friends who might be interested?"
