Should I or shouldn't I?

[Drolefille]

Try to pick the friendship back up, but if she was serious about the engagement, you Don't want to be the rebound guy.

Make an effort to see her and hang out.

If you're good enough friends, I think you'll know when she's moved on and ready for a new relationship.

[valkyrie]

If you want to date this woman, ask her out to dinner or whatever. If she's not ready to date, she can say no. If she agrees, just go out and have fun. I don't know how you or she could possibly determine whether you want to be in a relationship with each other until you've gone out at least a few times. Also, if you're already in the "relationship" mindset, be prepared to date her, really like her, and then be really bummed when she moves. If you can't live with that possibility, don't bother.

[RU OX Alum]

Tell her how you feel, apologize (not in so many words, maybe not apologize, but at least explain why you didn't ask her out when she was with other dude) and ask her out. Don't worry about it if she moves or not.

[RU OX Alum]

Or move with her.

[SOPi_Jawbreaker]

Originally Posted by RU OX Alum

Or move with her.

EEK EEK EEK

To PatriotGame:
How far is she moving? If she's just moving to the next town over, then like valkyrie said, just go ahead and ask her to a casual dinner. If she's moving several hundred or thousand miles away, then you have to ask yourself whether you can even deal with a long-distance relationship...if a relationship ever happened. Long-distance relationships take a lot of work, time, effort, trust, good communication, and maturity. If these things don't sound like things you'd be willing to put in, then you shouldn't even bother pursuing a relationship with her.

[valkyrie]

Originally Posted by RU OX Alum

Tell her how you feel, apologize (not in so many words, maybe not apologize, but at least explain why you didn't ask her out when she was with other dude) and ask her out. Don't worry about it if she moves or not.

I don't know, dude. I'd be totally creeped out if some guy told me he was into me out of nowhere and wanted to ask me out years ago.

[OtterXO]

Originally Posted by valkyrie

I don't know, dude. I'd be totally creeped out if some guy told me he was into me out of nowhere and wanted to ask me out years ago.

I would too! I think it's better to just ask her to hang out without explaining the motive. If she's feeling it and you get a good vibe from her then ask her to hang out again. Just treat it like a normal dating situation. Do not, I repeat DO NOT confess your love for her the first time you get together.

[AKΨ_BRO@DSU]

Originally Posted by valkyrie

I don't know, dude. I'd be totally creeped out if some guy told me he was into me out of nowhere and wanted to ask me out years ago.

Why? Maybe he was just too afraid to ask you out or valued your friendship enough not to allow other feelings to ruin it.

[shinerbock]

Red Light. No. Not at all. Turn and run.

From my personal experience, this wait and see, longtime friends thing rarely works out. Number one, you've been too tied up with this girl for too long. This causes expectations. Reality will probably not meet those expectations. Number two, she's got baggage. Do you really wanna deal with an ex-fiance? I don't. Personally, I'd absolutely move on. At the very least, I'd give it some more time before doing something. Life is weird, your paths will probably cross again.