Crossing the line from friend to romantic partner

[QUOTE=Saturn Dreams]
I don’t know if she just regards me as someone she can trust talking to without having him hitting on her
[/QUOTE]
I know a lot of guys like this. But they’re all one of the following: a. happily married b. gay or c. my dad’s age or older (at 30 I’m not really interested in guys older than 35 yet, but I’m aware it’s not always the case the other way around until there’s a bigger age gap). Since you’re no longer a and not b or c, she probably is aware that there is a possibility you could hit on her.

However, if you only said you suppose your wife is fine without elaborating, she might not realize you mean your divorced. You could just have meant your wife is cold and distant or you’ve been fighting. While it wouldn’t be wise to dwell on the breakup over dinner since that’d make you seem less than ready to have a new relationship, do make it crystal clear that you’ve divorced - just in case she has illusions that you still fall into catogory A above. If she looks pleased that you’re on the market again, it’s a good sign. If she just says “Oh” and looks uncomfortable…

I’m surprised no one has asked what a ROFLcopter is yet. :stuck_out_tongue:

[QUOTE=Pithy Moniker]
My wife and I were friends for a few years before we started dating. I was interested in asking her out for a long time but always worried about ruining a good friendship and kept putting it off.

Later, after we got engaged, we were talking about it and she told me that she had wished that I would ask her out since early in the friendship. She had never suggested it because she was worried about ruining a good friendship and she wasn’t sure if I even liked her that well.

My advice would be to step up and ask her out. If she’s someone that you like and think you could love, seize the opportunity before someone else does!
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Cheers Pithy,

I’ve already asked her out and we have a dinner date for next Friday. I’m just tying to elicit ideas so I can improve my chances for a next date without looking like a wolf in sheep’s clothing.

[QUOTE=elfkin477]
do make it crystal clear that you’ve divorced - just in case she has illusions that you still fall into catogory A above. If she looks pleased that you’re on the market again, it’s a good sign. If she just says “Oh” and looks uncomfortable…
[/QUOTE]

Good advice. I plan on telling her clearly that I’m divorced. I’ll make sure to study her expression when I tell her this news. Now, all I have to do is to make sure my eyes don’t look beady…

Print out a copy of the OP. Hand it to her before dinner and ask, “What do you make of this? I found it on my computer after I had written it.”