Active discussions

Meet the Other Phone. Child-safe in minutes.

Meet the Other Phone.
Child-safe in minutes.

Buy now

Please or to access all these features

Talk
AIBU?

Share your dilemmas and get honest opinions from other Mumsnetters.

Original poster

To date a guy who is going on holiday for a week with his female best friend who he once had feelings for?

38 replies

Thatoneisnice · 12/04/2026 16:05

I go back and forth between thinking im being crazy and then thinking im being unnecessarily insecure.

I met this guy at a gig last year and we were initially just friends. But we started spending more one on one time together doing things.. we went out for dinner, to see a play, on a few long distance hikes, to see a film, to a couple of other gigs.
I find him very attractive and I started to think maybe he found me attractive too.
Just lots of eye contact and things like that.
He had mentioned he had a female best friend hes known since they were children and I have met her briefly a couple of times. She seems like a sweet person.
He confided in me that the year previous he had developed feelings for her whilst they were travelling together and eventually built up the courage to tell her.
She reacted quite vaguely apparently saying 'she wasn't ready for any relationship' and he said it turned out she was seeing someone and it was more serious than he'd realised.
However on another occasion he told me they had since broken up and she had rang him crying about it.
But when asked 'how's that developing' he always said that it wasn't and he did not think she liked him like that.

Well fast forward to the last time I hung out with him and it was just a really lovely time. We spent the whole day together and after dinner ended up going for a few drinks.
I went to the station with him, he ended up getting the last train home after missing a couple! We hugged and it went on a touch longer than usual.
Off the back of this i messaged him to say that perhaps we should consider actually dating in a romantic sense.
He replied immediately to say he would like that. Then replied again in the morning even though I hadn't replied to him, to reiterate the same thing.

Hes been away with work fir a few days and we were in contact most days.. but hes now going away for a week with his female best friend I was talking about earlier. This was obviously arranged pre us deciding to go on a date but its making me feel quite unsettled.
Of course I dont want to say anything to him about that as we haven't even been on a date yet so its none of my business.
But at the back of my mind im thinking 'am I wasting my time here? Am I just setting myself up to be hurt?'

Another factor is that ive recently come out of a long term relationship. I wasn't looking to meet anyone and I wouldn't have gone for this its just I really like him.
In a way that puts more at stake for me

He is a few years younger than me (hes 24 and i am 29) and this is another issue. He has never been in a relationship before at all, of any type.
That would put me off on paper but in person he seems emotionally mature, sweet and intelligent.
He said it just never happened for him that he connected with anyone, and he didn't want to hook up with just anybody for the sake of it.

Am I being completely delusional for continuing to invest in this situation emotionally?
I want to be relaxed about it but I feel like I like him a bit too much iyswim

OP posts:
Idontjetwashthefucker · 12/04/2026 16:06

Nope

Classiclines · 12/04/2026 16:08

I would now bail out now OP.

CremeEggThief · 12/04/2026 16:10

What do you want?

Fine if you're happy with FWB.

Probably not for you, if you hope it will lead to a relationship.

Vconcerned1 · 12/04/2026 16:11

Aww op this sounds like frustrating timing. I empathise on the unknown! Just breathe... It's early days... I'd probably wait and see if he contacts you this week and try to put it out of your mind, then see if he gets in touch post-holiday to organise the date. If he's keen I imagine he'll message you and time will soon tell.

Snapespeare · 12/04/2026 16:13

Oh, I voted UNreasonable, because he's stringing you along, treating you like a plan B and - so you're being unreasonable to entertain this nonsense.

You've recently come out of a LTR, you're not looking for a branch to cling onto like a spider monkey working it's way through the rainforest canopy. Have a bit of you-time, cut him loose, don't be played like this..

Sartre · 12/04/2026 16:14

5 years is generally nothing but when one party is particularly young (under 25 imo) and immature, it can and does become an issue. I think it’s pretty clear he’s still hung up on her and if she agreed to go out with him, he’d jump on the opportunity and you wouldn’t even be taken into consideration. I wouldn’t consider dating him as a result personally.

Feelings don’t just dissipate generally, particularly when it’s unrequited but you remain friends. The person with feelings never wants to only be friends and always holds out hope it will eventually go further. He should have cut her off when she declined to go out with him.

BlueMum16 · 12/04/2026 16:14

Vconcerned1 · 12/04/2026 16:11

Aww op this sounds like frustrating timing. I empathise on the unknown! Just breathe... It's early days... I'd probably wait and see if he contacts you this week and try to put it out of your mind, then see if he gets in touch post-holiday to organise the date. If he's keen I imagine he'll message you and time will soon tell.

I agree with this.

Leave him to enjoy his holiday and see where things lie when he's back.

TheSlantedOwl · 12/04/2026 16:16

Detach and see what happens. He’s very young though.

ohyesido · 12/04/2026 16:17

Do you think he would choose not to sleep with her out of respect for you?

ThisJadeBear · 12/04/2026 16:17

He’s 24 and you are 29 just out of a LTR.
He hasn’t just worked out now you want to do date him. He will have known that for a while. He will have definitely known you are attracted to him.
He’s just going with the flow whilst you are already invested. This female friend is already more of a priority than you will ever be.
If you don’t mind no-strings where he will be sleeping with other women, proceed.
But if I were you, I would move on. Enjoy the fact that you have spent time with someone and had a good connection. But you could get very hurt if you are expecting more.

Original poster
Thatoneisnice · 12/04/2026 16:18

Sartre · 12/04/2026 16:14

5 years is generally nothing but when one party is particularly young (under 25 imo) and immature, it can and does become an issue. I think it’s pretty clear he’s still hung up on her and if she agreed to go out with him, he’d jump on the opportunity and you wouldn’t even be taken into consideration. I wouldn’t consider dating him as a result personally.

Feelings don’t just dissipate generally, particularly when it’s unrequited but you remain friends. The person with feelings never wants to only be friends and always holds out hope it will eventually go further. He should have cut her off when she declined to go out with him.

I think cutting her off would be a bit strong as shes a childhood friend and obviously a big part of his life.
But yes I do wonder at the continuing to go on holiday alone with her. It suggests he doesn't really want to move on from his feelings for her. Well to me it does anyway. If I had romantic feelings for someone that weren't returned I probably would not think it wise to seek out more bonding experiences with them.. id want a bit of space to recover

OP posts:
Original poster
Thatoneisnice · 12/04/2026 16:20

ohyesido · 12/04/2026 16:17

Do you think he would choose not to sleep with her out of respect for you?

Honestly I dont think they will be sleeping together on this holiday, I 100% trust that wont happen. Its more his feelings I'm worried about and whether ive just connected to someone who will never connect to me because they are in love with someone else!

OP posts:
toomuchfaff · 12/04/2026 16:20

theres 3 different outcomes and you can influence neither of them.

Something happens with her
Nothing happens with her because she doesnt want too
Nothing happens with her because he holds you in high regard now

Leave him to enjoy his holiday and see if he contacts you throughout (likely 3), or after (1 or 2). All depends.

ohyesido · 12/04/2026 16:21

Thatoneisnice · 12/04/2026 16:20

Honestly I dont think they will be sleeping together on this holiday, I 100% trust that wont happen. Its more his feelings I'm worried about and whether ive just connected to someone who will never connect to me because they are in love with someone else!

Show quote history

Spare yourself the pain

Nowvoyager99 · 12/04/2026 16:23

No way would I get involved in this shitshow

Original poster
Thatoneisnice · 12/04/2026 16:24

toomuchfaff · 12/04/2026 16:20

theres 3 different outcomes and you can influence neither of them.

Something happens with her
Nothing happens with her because she doesnt want too
Nothing happens with her because he holds you in high regard now

Leave him to enjoy his holiday and see if he contacts you throughout (likely 3), or after (1 or 2). All depends.

Yeah you're right.
I need to calm down and just see how I feel about it all when he gets back.

OP posts:
toomuchfaff · 12/04/2026 16:27

Thatoneisnice · 12/04/2026 16:24

Yeah you're right.
I need to calm down and just see how I feel about it all when he gets back.

Show quote history

isnt there an old saying about if you can influence it, leave it...

Handle every stressful situation like a dog. If you can't eat it or play with it, just pee on it and walk away.

5128gap · 12/04/2026 16:29

If I were you I'd not consider yourself as having any sort of thing with him until he returns from the holiday, at which point you can see where the land lies. Certainly there would be no reason at this point to consider yourself dating him on an exclusive basis. So in your shoes I'd be getting on with my life and if you reconnect after his holiday and you both want to progress something you can.

Boxiboxi21 · 12/04/2026 16:36

He's never been in a relationship before. You will be teaching him EVERYTHING. Conflict resolution skills. Fair compromise. Reasonable expectations. Maybe even physical intimacy. Don't do it, and do you want kids? He's likely a good 10-15 years away from them.

Original poster
Thatoneisnice · 12/04/2026 16:40

Boxiboxi21 · 12/04/2026 16:36

He's never been in a relationship before. You will be teaching him EVERYTHING. Conflict resolution skills. Fair compromise. Reasonable expectations. Maybe even physical intimacy. Don't do it, and do you want kids? He's likely a good 10-15 years away from them.

Yeah the teaching things is an issue that plays on my mind.
I already have 1 child with my ex. He is 8.
Again this is a big experience gap.
Im absolutely not looking to introduce anyone to my son. My ex is a good dad and has him 50/50 and there are no issues there.
But still its a massive experience gap.

I just connected with this guy so well as a friend.
I hadn't even considered dating before this even though ive been separated from my ex for nearly a year now.
The thought filled me with horror until now.

OP posts:
Error404FucksNotFound · 12/04/2026 16:43

I wouldn't get myself in the middle of that bloody mess

Elanol · 12/04/2026 16:47

I had a boyfriend who'd been part of my social circle for years. The group took an annual trip abroad. I never went as it wasn't my sort of thing.

When we got together he was undecided about going that year. As it happened I was on annual leave that same week, so he decided to spend the time with me instead.

The following week he announced that he'd booked and was going on the holiday after all. He was the only bloke with 26 girls (yes, 26 not a typo) I was left on my own the whole week.

He was surprised when I ended it on his return.

If he couldn't see what was wrong with that shit there's no hope. He asked if I thought that sort of thing might be why his previous girlfriend left him.......

Yes. I expect it was.

Elanol · 12/04/2026 16:50

She reacted quite vaguely apparently saying 'she wasn't ready for any relationship

You only have his word for this. Or it could be true that she didn't want a relationship but happy to shag him.

Planesmistakenforstars · 12/04/2026 17:06

Nope. If he had pursued you, or in his admission about his feelings for his friend he had said it had faded and he no longer feels that way, then maybe. But he is probably just taking the option he's been given (you) and not the one he wanted (her.) Sorry to put it like that, and good for you putting yourself out there and going for it, but you are not his first choice, and if she is in the picture you never will be. If she wants to shag him then he'll be off like a rat up a drainpipe.

outerspacepotato · 12/04/2026 17:18

There's multiple reasons this is a really bad idea

He's got feelings for another woman he's going on holiday with. He calls her friend but that's no guarantee they will stay platonic. She's keeping him around as a backup. Just like you will be a backup in case nothing does happen with her. Do you want to be a backup plan?

He says he's had no experience with being in a relationship so he's emotionally immature. Do you really want to be his older relationship trainer? That would be a turnoff.

You have a child. This guy is younger than you and supposedly no relationship experience, so no experience dealing with the complications of a relationship where kids are involved. That would be an absolute no.

I think you'd be foolish to continue pursuing this guy. He's already got his Ms Right in mind and it's not you, you're just Ms Right There..