Can I ask him out if he’s dating someone else but it’s not yet serious?

[Jyvoc]

Hi Folks, seeking some advice. My male friend has been dating a woman for just over a month. Is it appropriate to throw my hat in the ring, romantically speaking?
For context, he and I have been friends for 20+ years. There’s always been chemistry on both sides, but we’ve both previously been in long term relationships so have never pursued anything other than friendship.
We’ve only recently reconnected having been out of touch for a while due to other personal priorities. However, he did say that he hadn’t reached out sooner as he thought he had done something to ruin our friendship (complete misunderstanding, now resolved).

Have I missed the boat in this? Should I bow out quietly now? Not sure what the etiquette here should be, if they’ve only been dating a month.

Well, I have no issues with you asking him out if you’ve had some kind of revelation that he’s your dream man. If he’s not interested and/or serious about the woman he’s seeing, he can say no.

But I do wonder why it’s taken you this long, unless you’ve literally both been married since the day you met until just now, especially as you seem to have fallen out of touch.

If you’re serious and can cope with the possibility of him saying ‘Ew, have never thought of you like that, and I really like Chloe’, go for it.

You only get one life.

A life lived in fear is a life half lived.

Better to have loved and lost than never to have loved at all.

I mean, I've got a book of these sayings appropriate for the situation...go for it!

Multi dating casually - which is usually when people meet via OLD and have a conversation about both seeing other people is very different imo to trying to ask out someone you already know is dating.

Its not a good look imo

Tbh, I'd probably do something along these lines

Nothing ventured, nothing gained; all's fair in love and war and all that 🤷🏻‍♀️

I doubt you know about her at all if it was that casual, men make it clear when they’re unavailable, if he thought he had a chance with you, then he’d be asking you out.

Leave it.

Something would have happened over the past 20 years if it was going to.

Agree with this , leave him alone.

I can’t think of anyone I know in their 30s that’s dating multiple people, female or male.

Most people prefer to focus on one person, it’s silly online postings and cliche films that make people think they should be dating multiple people at once w.

I'd be inclined to ask "You and Sally, is that a serious thing?" and take it from there. And I have been "Sally" in this situation and just wanted the best for my man. I'd hate to think I was depriving him of a relationship that might suit him better. 💗 I really don't get this "Hands off, he's mine" attitude. Life is short.

I wouldn’t ask him out, but I’d meet him as a friend, then casually ask if it’s serious and if they’ve made it exclusive. Then you have your answer and can act accordingly.

He only sees you as a friend. Don’t embarrass yourself.

There's only one way to find out, though!

Maybe you could get to know him as a friend first

Hi Spindleweed. Thanks for this, it’s definitely food for thought.
To address your question, yes we were both in committed relationships when we met (in our 20s) until a couple of years ago.
In the small window when we were both single, he did suggest we go on a date together. However, I acknowledged at the time that I was attracted to him but thought we’d be jumping in too soon (both breakups being quite recent at that point). The friendship continued as normal for a couple of weeks and then I had a bereavement and was out of touch socially in general whilst recovering. He assumed he’d blown the friendship and didn’t want to push it (he wasn’t aware of the bereavement).
When we reconnected a few weeks ago I assured him that I hadn’t fallen out with him and explained about the loss.
I hope this addresses the point about why we hadn’t been romantically involved. Perhaps I was too cautious at the time! But what’s done is done I guess.
In any case, you’re answer was thought provoking and I appreciated it.

A friend of mine did this and they are married now. She sort of found out first that he wasn't that keen on the current partner. She was also really keen on him. I personally would say if you are really serious then go for it.

I let a secret crush go by not telling him.

So he has already said he's attracted to you "in that way" - in these circumstances, I think it would be madness not to seize the bull by the horns, as it were!

Presumably you are mature enough (and respectful of him enough) to step aside if he says it's a proper "thing" after 1 month, or that he wants to see how it goes. But on the basis of what you've said, there's no harm in wearing your heart on your sleeve, and the risks of not doing so are greater.

I don't think you should ask him out as I don't think I'd want another female to do it to me.
I think the fact that things panned out how they did in those moments when you were single say it all. If he really really liked you then I feel he'd have waited a bit longer before starting to date someone else.
I'd also worry that if I said something and it didn't work out, I could have sabotaged his chance with this other woman.
All this is my personality type to a tee though, so might not be how you'd feel about it.

I'd definitely continue to be friends with him if you feel able to do it. He's either found his person and then you'll be happy for him in the long run or he hasn't and they'll split and you can share how you feel then.

I’d go for it, and just make sure you are really respectful about it. Don’t allow him to string you or her on and don’t engage in any extended flirting or intimate behaviour, beyond you telling him, without him being single first.

If you’re let down, however, I would step away from the friendship completely.

Based on what you've said OP, particularly him worrying that he'd ruined your friendship (by asking you out?), it sounds as though he thougth you'd friend-zoned him and were letting him down gently.

I'd compare notes with him rather than wait for him to put a ring on her finger because he doesn't think you're available 🤡

Meet up as a friend.

If he’s fallen for this woman (it can sometimes happen quickly) he’ll tell you. Then, you leave well alone.

It’s more likely that the relationship (if they’re choosing to call it that already) is still finding its feet. It’s worth finding out.

But I wouldn’t accept an overlap. If he wants to go on a date with you he needs to show some respect to you both and finish with her first. No excuses.

I would be subtle about it. Have coffee as friends, work up to lunch… test the water.

I don't think you should ask him out as I don't think I'd want another female to do it to me.

Maybe not but what if he was only with you because he thought the woman he really wanted wasn't interested?

I think the fact that things panned out how they did in those moments when you were single say it all. If he really really liked you then I feel he'd have waited a bit longer before starting to date someone else.

But real life doesn't work like that. People often date others while they're interested in someone else in an attempt to get over them. What would he have 'waited a bit longer' for?

If he chooses the OP over the woman he has dated for a few weeks, then it wasn't meant to be anyway. If he doesn't, well, then she has her answer.

Yes I agree with this

Given this update, I think you should say something now.

He has said he liked you, and you like him. He can make his mind up before he commits to this other woman.

don’t leave it until later. It’ll be messier then.

It’s fine if they’re not exclusive/having sex.