Long-time lurker. I've read these threads, and hate them. Swore I would never make one. In my early-mid 20s (so is she). Anyway.
The Question
Basically, I have a good friend that's a chick. I want to tell her I think we should start dating. If this works, great. If this doesn't work, the friendship will be awkward or fall apart
The Backstory
Here's the backstory, in case anyone cares:
About August/Sept of 2009: met this girl.
- went out a few times
- nothing happened
- no chemistry
- 'relationship,' to any degree, ended.
- she got into a relationship/boyfriend with another guy.
Didn't talk to her, txt, phone, gchat, anything for six months.
About Jan. of 2010, she randomly starts texting again, asking what I'm doing, if I want to hang out, etc. Totally weird. We eventually start hanging out occasionally, and it turns out she was on the rocks with that guy.
As she's on the rocks with that guy, she starts dating an old friend of hers from years ago, and moves from BF1 to BF2.
Through April and May '10, we continue to get closer and are pretty good friends at that point. She's a student so we don't see each other at all all summer long.
Now it's October, and she just broke up with BF2.
I'm solidly in the friend-zone.
On the other hand, BF2 had been an old friend from way back, who on a lark one weekend professed his love and they started dating. So maybe being in the friend-zone isn't as fatal as it usually is?
My Course of Action
I think I am going to casually mention, in a joking way, that we should start dating. Probably when we're both out drinking at some point. If she gives me a stone cold glare or is cold to the idea; well it was a joke anyway and/or I was drunk. And if she's receptive to the idea, then perfect. The other option seems to be blatantly coming out and saying "I think we should start dating" which would ruin the friendship if it failed.
The Question
Basically, I have a good friend that's a chick. I want to tell her I think we should start dating. If this works, great. If this doesn't work, the friendship will be awkward or fall apart

The Backstory
Here's the backstory, in case anyone cares:
About August/Sept of 2009: met this girl.
- went out a few times
- nothing happened
- no chemistry
- 'relationship,' to any degree, ended.
- she got into a relationship/boyfriend with another guy.
Didn't talk to her, txt, phone, gchat, anything for six months.
About Jan. of 2010, she randomly starts texting again, asking what I'm doing, if I want to hang out, etc. Totally weird. We eventually start hanging out occasionally, and it turns out she was on the rocks with that guy.
As she's on the rocks with that guy, she starts dating an old friend of hers from years ago, and moves from BF1 to BF2.
Through April and May '10, we continue to get closer and are pretty good friends at that point. She's a student so we don't see each other at all all summer long.
Now it's October, and she just broke up with BF2.
I'm solidly in the friend-zone.
On the other hand, BF2 had been an old friend from way back, who on a lark one weekend professed his love and they started dating. So maybe being in the friend-zone isn't as fatal as it usually is?My Course of Action
I think I am going to casually mention, in a joking way, that we should start dating. Probably when we're both out drinking at some point. If she gives me a stone cold glare or is cold to the idea; well it was a joke anyway and/or I was drunk. And if she's receptive to the idea, then perfect. The other option seems to be blatantly coming out and saying "I think we should start dating" which would ruin the friendship if it failed.








