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Original poster

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

67 replies

Jyvoc · 21/07/2025 14:54

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.

OP posts:
JillianFife · 21/07/2025 19:35

You are silly if you dont tell him

Elektra1 · 21/07/2025 19:38

I think it would look like you’re primarily interested for competitive purposes. I’d let it be, stay friends, and try your luck when he’s single.

The other risk of saying something now is if he’s really into the new woman, tells her, she doesn’t like it and that ends your friendship of 20 years.

Freeflight · 21/07/2025 19:40

@GreyCarpet id still not want another female (who had known him long enough to make her move) to swoop in and make a play for someone I was dating in the early days.
At 1 month in he's likely still figuring his new partner out and he should have the ability to do that.
If he's really that interested then things won't last as she'll "never compare".

Like I've said, my personality type is that I wouldn't want to cause hurt (and I get the feeling the op doesn't want to either). Making a move could cause pain to someone and it would have been an intentional move so it's a risk I wouldn't take.
Sometimes you just have to live with the choice you make and see how things pan out. It was the Ops choice to say no and maybe that's a chance missed, but that was the chance. I personally don't feel this is another opportunity unless he mentions that things aren't going well etc.

BunnyMcDougall · 21/07/2025 20:01

Partner? After 4 weeks?

Spindrifts · 21/07/2025 20:04

Why not just stay friends with him? If it works, just keep it going in a low key way. Perhaps the new relationship won't last but you won't know unless you let it run its course. In the meantime live your best life and you never know, he must notice how you sparkle. No one will be hurt and matters will run their natural course.

MyHardySquid · 21/07/2025 20:06

You only get one life. I would take the chance - tell him how you feel and take it from there, don’t ’ask him out’ as such, just tell him your feelings.

Beachtastic · 21/07/2025 20:07

Spindrifts · 21/07/2025 20:04

Why not just stay friends with him? If it works, just keep it going in a low key way. Perhaps the new relationship won't last but you won't know unless you let it run its course. In the meantime live your best life and you never know, he must notice how you sparkle. No one will be hurt and matters will run their natural course.

Surely the strain of making every effort to "sparkle" while pretending to just be friends is a bit nuts, and far more damaging to the (1-month!) "other romantic interest" than just being straight with him and comparing notes on expectations.

JillianFife · 21/07/2025 20:07

Personally I wld get drunk and full on to him

Ilovecrispstoomuch · 21/07/2025 20:09

Tell him! Always better to regret doing something than not doing it IMO !

a month isn’t very long. You obviously have a connection 🙂

Laughlikeadrain · 21/07/2025 20:57

Can’t believe so many people telling OP to give up personal happiness for a stranger!

He has known the other woman for 4 weeks. Would see the point if this was an established relationship. But it’s been a few dates max.

the other woman may not even be that fussed.

OP- let him know you like him. He can make his own mind up and make it clear you’ll understand if he wants to continue seeing the other woman.

Original poster
Jyvoc · 21/07/2025 21:03

Thank you all so much for taking the time to think about and respond to my questions. It’s really reminded me how kind and thoughtful people are to take time for a relative stranger.

I can see 4 main schools of thought in the responses.

  1. Say nothing, though he’s only had a few dates with the new lady, seriousness is subjective. It could cause undue pain and could also ruin the friendship.

  2. Share my interest before the new person becomes serious but do so respectfully and manage expectations for maintaining the friendship if he wants to moved forward with the new person.

  3. Sound him out subtly and understand more about where he’s at before deciding on a course of action. If he’s already serious or sees the potential with the new person then say nothing.

  4. Subtly let him know I’d be open to dating him and leave it open to him to either make a move or not. I note, if he doesn’t respond then this, in itself, is an answer.

(FYI, “get drunk and jump on him” did make me giggle)

Again, thanks all for the support and advice. I’ll be giving these some serious thought. (There will probably be a pros and cons list)!!

OP posts:
andherewegoagainonmyown · 21/07/2025 21:17

Fluffypotatoe123987 · 21/07/2025 14:58

I would maybe ask to meet up and do something fun like snowboarding or a comedy club as friends. Generally ask how hes getting on with new dating partner etc etc. Get an idea of how things are. Maybe drop in there aww thats a shame I always had a thing for you. But looks like ive missed my chance. Await his reaction and laugh it off if he really likes her etc and say your happy being friends.

I think this is good advice.
well, apart from the snowboarding as I can’t imagine there’s much snow going on in your town unless you live in maybe like The Himalayas?

Sally2791 · 21/07/2025 21:21

Go for it! Otherwise you’ll regret it for ever

JMSA · 21/07/2025 21:24

Jyvoc · 21/07/2025 21:03

Thank you all so much for taking the time to think about and respond to my questions. It’s really reminded me how kind and thoughtful people are to take time for a relative stranger.

I can see 4 main schools of thought in the responses.

  1. Say nothing, though he’s only had a few dates with the new lady, seriousness is subjective. It could cause undue pain and could also ruin the friendship.

  2. Share my interest before the new person becomes serious but do so respectfully and manage expectations for maintaining the friendship if he wants to moved forward with the new person.

  3. Sound him out subtly and understand more about where he’s at before deciding on a course of action. If he’s already serious or sees the potential with the new person then say nothing.

  4. Subtly let him know I’d be open to dating him and leave it open to him to either make a move or not. I note, if he doesn’t respond then this, in itself, is an answer.

(FYI, “get drunk and jump on him” did make me giggle)

Again, thanks all for the support and advice. I’ll be giving these some serious thought. (There will probably be a pros and cons list)!!

You sound like a good and emotionally intelligent person. I’m sure you’ll make the right shout!

Bayou2000 · 21/07/2025 22:03

Bayou2000 · 21/07/2025 19:23

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

I spent 18 mths seriously working a friendship/steering in into romantic territory. I won’t lie it was seriously hard graft, I did most of the heavy lifting, including once false start where I jumped too soon but I persevered and we are now quite blissfully in love.
Just be prepared for the long game if you are really serious.

Beachtastic · 21/07/2025 22:05

Jyvoc · 21/07/2025 21:03

Thank you all so much for taking the time to think about and respond to my questions. It’s really reminded me how kind and thoughtful people are to take time for a relative stranger.

I can see 4 main schools of thought in the responses.

  1. Say nothing, though he’s only had a few dates with the new lady, seriousness is subjective. It could cause undue pain and could also ruin the friendship.

  2. Share my interest before the new person becomes serious but do so respectfully and manage expectations for maintaining the friendship if he wants to moved forward with the new person.

  3. Sound him out subtly and understand more about where he’s at before deciding on a course of action. If he’s already serious or sees the potential with the new person then say nothing.

  4. Subtly let him know I’d be open to dating him and leave it open to him to either make a move or not. I note, if he doesn’t respond then this, in itself, is an answer.

(FYI, “get drunk and jump on him” did make me giggle)

Again, thanks all for the support and advice. I’ll be giving these some serious thought. (There will probably be a pros and cons list)!!

I'm sure he'll go for you. Who wouldn't, you sound great OP!

Just remember to invite us to the wedding 🥳🥳🥳

Pbjsand · 21/07/2025 22:33

time is not on your side here. If it were me, I’d just be honest and text him, “was surprisingly disappointed to find out you’s just started dating someone. Thought we were both single, finally!” And leave the ball in his court.

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