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

Not only is he using you as a distraction to see if it helps him go off her, but she is stupid to go on holiday with him knowing he has feelings for her.

Swerve them both and leave them to their mind games. Take some confidence from the mutual attraction and shine for someone who is worth it.

Won’t happen. Sorry. If she comes onto him during that holiday, he’ll be like a rat up a drainpipe, with the OP being a distant memory.

Yabu for going out with him.
Yanbu for wanting to finish it.

RUN
I mean this kindly, but man up and have some self respect.

Who goes on holiday for a week with a friend of the opposite sex in April? Are they going abroad? Do they have mutual interests that the holiday is based around?

Surely something will happen between them but if it was booked before you two got together then there's not much you can do about it.

See how you both feel when he gets back?

Why would you even put yourself in this situation? Do you want to be worrying about if there’s still a spark between them or not? Run a mile it’s not for you.

Something very similar happened to me. I waited to see how the holiday would pan out. It was over 20 years ago and we're still together and still happy. And he's still just friendly with the woman. So my advice is, since he had arranged this before dating was on the cards, just wait and see how he is with you when he gets back. I hope it goes as you would wish.

24 is young who knows what he wants .. I'd stop with thoughts of being with him emotionally until he is back from his best friend holiday.
Maybe pick it up after that see how the land lies takes patience though .
Depends if you can be bothered with best friend in the background she could be a thorn in your side.

Waste of time

I haven’t read the whole thread so apologise if this has already been said, but I suspect once this girl knows someone else is interested in him/he’s interested in someone else, she will suddenly become a lot more keen on hanging onto him. It’s human nature, men and women are absolutely capable of enjoying the attention from someone then the moment that attention starts getting diverted they don’t like it. My current partner’s wife left him and he spent nearly three years trying to win her back from the guy she left him for, then the moment he met me and things started looking serious she suddenly began making noises about wanting him back and using nasty tricks to divert his attention away from me and onto her. It was a horrible experience and caused me a lot of pain, wouldn’t wish it on anyone.

Personally I would steer clear of this situation, especially as you’ve just got out of a LTR yourself, I think it has heartbreak and confusion written all over it.

I think this is the honest conversation you need to have with him as regardless of the holiday it’s the elephant in the room and you don’t want to be in a relationship where you can’t speak openly, this will be a good test of his real maturity
be calm and kind but I’d for sure be asking him where he’s at with his feelings for his friend, keep in mind that you initiated the move to dating knowing this was already a thing and you’re apparently not concerned that they will sleep together
I wouldn’t necessarily write him off and assume you’d be a second choice but I also wouldn’t want to be a relationship where I felt I couldn’t be honest about my feelings

After reading you have a child, it gets worse.
It is not about an introduction.
You are a grown up, a mum, don’t be sitting around waiting for this young man to come home from holiday with someone he has feelings for.
One who has never had a relationship,
You are at two different stages in life and it can never work.

@outerspacepotatosaid it all! He’s not really that bothered about you.

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..

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.

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.

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.

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

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.

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.

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.

No way would I get involved in this shitshow

Spare yourself the pain