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

[Thatoneisnice]

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

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

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.

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

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.

Waste of time

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.

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.

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.

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?

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.

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.

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.