I can't imagine, with the history you've got, that making a move would be any kind of risk to your friendship. At worst, if he's not interested it might be awkward the next time you see him, but you'd get past it soon enough. And from what you've said, I wouldn't be at all surprised if he felt the same as you do.
You've got the advantage of being the (slightly) younger party, so you can always blame it on "immaturity"... maybe the reason he hasn't made a move himself is that he thinks he'd be taking advantage.
Good luck. It'll make a beautiful "how we met" story if it works out :)
I think that you should talk to him about it. Honestly, I am the type of girl who could come up with some crafty way to end up locked in a passionate make-out session, but that is the old me... I'm starting to think that never really got me anywhere. You are lucky you haven't hooked up with him. It makes it more real. I don't know the situation, but I did have a friend who was very in love with her best friend. She told him and he rejected her. A year later, he asked her out. All of us (her other friends) were super skeptical and worried. Another year goes by and he proposes. Now they are very happy. She talked openly to him and the worst possible result happened... but in the end it was much more important for her to be honest,
Let him know how you feel, if he's a true friend and he's not interested then he'll simply inform you of that and if he is then go forward with it. There are some people that are just extremely caring and giving people and it doesn't always mean they're interested but he could be, you never know.
Tricky situation. Have a friend like that. In the end, things did happen, and in the end we did discover we are better off as friends. We are just really close and I can also turn to him no matter what it is. Wasn't even weird after it all happened.
If he doesn't have another woman in his life, then whether he likes you or not, asking him/telling him how you feel will not damage your friendship. Trust me on this.
It's apparent that he doesn't want more at this time. He knows how to ask for more. Remember ? He was married before. It sounds like things are going just fine. Give him some more time to make his move, and if it doesn't happen within a reasonable time (in your estimation), tell him that you love him and that you want to be married to him. Tell him that he should let you know if he wants to be married to you or not. Give him a week to let you know because if he doesn't want to marry you, you are going to persue other options, because you want to be married. Until he is forced to make a decision, he will let things be as they are now because there is nothing to lose. That's how my then girl friend got me to make a commitment. When I realized that I could actually lose her, I decided I wanted to keep her.
I'm sorry, but this really sounds like terrible advice. Say nothing at all and then spring an ultimatum on him that he has to marry you or lose you altogether? All that'll do is (a) make him think you're crazy and (b) make him think you were never friends, only keeping him around because you wanted someone to marry. You'd risk driving him away even if he was previously interested. If he's got intimacy issues, forcing a serious relationship on him when he isn't ready could make him want to run a mile.
Why don't you just ask him?
So you're getting married but flirting with someone else? Smh
@Indie Yikes, go back and read the details. And then learn how the past perfect tense works.
I skimmed thru the details. My apologies. At least take him out to coffee. See if you can feel him out and if you can tell him how you feel. He may feel the same way you do but may not want to bring it up. Maybe tell him first that you really enjoy being with him and go from there.