Should I or shouldn't I?

[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.