Feel like a lovesick teenager.

[incognitiomode]

I'm 40 and should be more mature than this, but really struggling.

I've been divorced for about 3 years now, all very civil and no other people involved. Happily single, not even really dating or looking to meet someone new.

At the start of December, I bumped into an old friend, who I've known for years. We always had a fun friendship, nothing intimate at all, but lots in common. He married and moved away and we lost touch apart from occasional facebook updates etc.

We've been chatting for the past month, mostly texts, a couple of coffees and phone calls. It's all stoked up this massive crush for him and I'm literally feeling lovesick and ridiculously out of practice. He's also divorced, a little while before me. He hasn't made any kind of move, but is very caring and attentive. I've been wanting to ask him on an actual date and bottled it... then today, he mentioned being set up on a double date and now I'm second guessing everything.

YABU- he's obviously not interested in me like that, so no point in asking him out and risk the rejection

YANBU- I should take the risk

Life is too short, go for it! He may think you’re not interested

Oh just ask him out! You've nothing to lose and everything to gain.

Instead of plain outright asking and fearing rejection (I share the same fears as you), perhaps you could drop a few subtle hints into your next coffee meeting?

Good luck, I hope it goes well with the outcome that's desired.

As he is dating but hasn’t asked you for a date I think it’s safe to say he sees you solely as a friend. That’s a shame as you’ve developed such a crush.

But you haven’t really got anything to lose by asking him for a date. Obviously you’ll have to be very clear that it would be a date and not friends meeting up. Yes, if he says no,that might end your friendship or at least make it awkward and result in you seeing each other less frequently: but surely you’d need to distance yourself from him if he starts dating. You wouldn’t want that in your face if you want him for yourself.

He might fancy you back, but is afraid of losing your friendship if he asks you out.

then today, he mentioned being set up on a double date

if he mentioned this because he was "being set up" on a double date with someone else, that means he said it for a reason, so you know he's dating (but not you).

if it was me, I'd want to cut through the intrigue and complexity of the "double dating with someone else" - by coming straight out with it "shall we go out for lunch?" and see if he signals any motivation to take the relationship onto a different footing. Otherwise you're going to miss the boat and kick yourself for not saying something.

Can you suggest a joint activity without calling it a date?

He either mentioned the date to see how you would react or to make it clear he wasn't interested in dating you. Realistically if you've developed this crush the friendship is probably doomed anyway- so nothing to lose by speaking to him about it.

Perhaps he wanted you to know he's dating, as in, he's available?