Should I Go For it With My Friend?

[Nouveaunew]

My problem isn’t a major one but I’d appreciate an outside opinion as I’d rather not talk to friends about it as I don’t want to badmouth this man to others.

I’m a 40 something separated woman and I recently met my 40 something separated male school friend for the first time in over ten years at another school friend’s wedding. I was looking forward to a chat with him but I wasn’t expecting to feel such chemistry - and I really did — I get the strong impression he did too. I haven’t been with anyone in years as my heart took a beating from the separation & even before my husband, my heart took some hard knocks. I had some negative experiences with men, one of which was quite serious and it left me feeling afraid of being intimate with men.

To unexpectedly meet a man I’ve known all my life and to realise we’re both single and to realise I might have sexual feelings for him - which I really didn’t think I did - was such a wonderful feeling. We kissed a lot growing up as teenagers but we were not compatible relationship-wise.

I would’ve loved if he had kissed me at the wedding and to be honest, that’s all I’d like — just a bit of romance and physical closeness. I’m not looking for a new husband, believe me. There was such attraction, warmth and caring between us. I didn’t know I could feel that way about anyone again.

So the problem is … he’s mean with money! He was the only one in our old group from school who didn’t buy a round of drinks that night at the wedding and my heart sank when I realised he’s still mean. I took a long break from hanging out with him once when we were younger after he landed me with a large bill and claimed to have ‘forgotten’ his wallet. Even writing that makes me feel so angry at him and I wonder if I’m just settling for scraps. I’d like if we could have some romance etc and maybe mend one another’s hearts a bit — I’m NOT looking for a big relationship with him but I’m afraid his tightness will get me so angry that I’ll lose all attraction to him. (Don’t even ask me why he’s always been so mean with money - he comes from a much wealthier family than I do, has a good job and has fewer outgoings than most of us there that night but it’s just the way he’s always been as long as I’ve known him, which is since primary school. He isn’t going to change).

What do you think? Do I lean in to what could be a lovely experience for us both or do I steer well clear? How much of a dealbreaker is tightness with money?

Give him a hard pass and just enjoy your kissing fantasy over a glass of wine. He is who he is, and that hasn't changed. Don't allow him in, it's not going to work.

I think someone once said on here ’mean with money mean with love’. It has stuck with me ever since.
I was talking with my friend the other day, we are both of Irish heritage though born in UK , and we were laughing about the Irish way which is where you are fighting to pay and how we have inherited that 😂

Steer clear - leopards don't change their spots.

I wasn’t expecting these responses funnily enough and given my history I feel I have to be careful not to make a big mistake!

But it is annoying! I think I was worried I was becoming asexual or that I was gay and had only just realised and feeling so attracted to him made me feel so good and it was just such a bummer when I realised he’s still tight. I just don’t get it.

Living with someone who is mean with money will mean that even if you don't live a long life, it will bloody well feel like it.

The thing is, someone who is mean with that money is literally just thinking of themselves. They are totally selfish. They are never part of a relationship team. They set themselves apart from the other partner and are happy if they make money out of that person.

Why on earth would you want to be with someone like that?

If you still get angry thinking about how he landed you withheld bill when you were younger, imagine experiencing that again but this time even worse because you’re having a physical relationship with him. He’s still mean with money and won’t change, you’ve acknowledged he won’t change. It might make you feel better for a short time but I think long term you’re going to be mad at yourself and ruin a friendship with him.

The eternal optimist in me says go for it. You only live once.

My only caution would be that it might be “fake” attraction. Just lust. Fuelled by a few drinks and a wedding. It could well be your emotional systems resetting themselves after your separation.

Being tight with money wouldn’t be a dealbreaker for me – I’d just start calling him Scrooge or asking if his pockets are sewn shut, etc. Just don’t sub him any money or offer to pay for anything.

Have you made plans to see him again?

The eternal optimist in me says go for it. You only live once.

That's so true, you only live once. So why would you waste your precious time on man who you know you're not suited to? 🙄

Quite often 'eternal optimist' = doormat.

Thanks for your comments. It really is such a detestable trait. That’s why I was so disappointed. Maybe I need to get that physical excitement from someone else! It has been YEARS since I’ve as much as kissed a man so maybe there is an element of fake attraction. I had a dream last night the pair of us were prancing around naked together!

We’ve arranged to meet up again. I was excited about it but a part of me was thinking ‘oh he might change’ etc. I’m done with the whole ‘he might change’ thinking (I think!!!)

He hasn't changed in almost 40 years...

People who are tight with money but happy for others to foot the bill are selfish and inconsiderate. Being tight with money but also not letting anyone else pay for you is different. This man is the former. And if he doesn't have the integrity to want to pay his own way/be not take advantage of others' kindness that means he will have other unpleasant traits as well.

It would feel like you are having to pay for male company if dating him means you will be shelling out for dates, meals, holidays, etc. I'm sure you can do a lot better. If you're going to have to pay for a bloke, you might as well get a hot, toy boy....

Yes, you are 'settling for scraps'.

I think he’d pay his way on holidays etc but it’s just such a bummer that he hasn’t grown out of the penny pinching. I had forgotten how tight he is until it was clear he wasn’t getting his round in. So disappointing as it does show selfishness.

Good advice all round. Don’t want to walk into another dead-end. Maybe the good that’s come out of it is that I’ve woken up sexually … maybe I just need to run with that and try to find some physical closeness elsewhere. I suppose I knew he’d be safe and I know a lot better now than to get too physically close to anyone I don’t know well.

See it as a positive that you are getting your mojo back but don’t waste it on him. Tight bastards are always bastards.

You could meet him again but forget YOUR wallet and see what happens?!

Thanks @Nopetryagain ! Overlooking and justifying is what got me to be single, separated in my 40s so I guess it’s time to finally pick up on the red flags early on.

@VeryQuaintIrene
That’s hilarious and I love it but I’m just not sassy enough to pull that off.

Tight bastards are always bastards it really is such a horrible trait. I don’t know how he’s got away with it for this long. You’d think by now he’d have been pulled up on it but I guess he just has not changed

Hmm. Surely it’s worth a conversation? If you felt that chemistry, and he did, and you get on, I’d be inclined to bring it up and see what he says when you ask him about it. You’re both older and wiser now, it’s easier to talk about this stuff as adults. You never know, he might open up, show some self awareness about it, add some context to his meanness - weird childhood, parents odd with money etc - which could transform things. At least you’d know you’ve tried too.

He’s probably got away with it because he is somewhat sexy/attractive hence you warming to him. You deserve better OP!

IMO you could see him for a bit of fun sounds like you need some fun. The problem might be that you really fall for him and the not paying his way would definitely get to you and you may be heartbroken once again. But if you can have fun without falling for him or breaking into your savings go for it

But if you can have fun without falling for him or breaking into your savings go for it
Ha ha!! That’s a good line. I’d love to have a bit of fun and boy oh boy do I need it! but yeah, I’m afraid I’m not really a person who can separate things out like that. Is actually Just love some kissing and affection … I’ve been just starved of it and it seems so hard to come by . Online dating is a joke.

I won’t be having a conversation about it to be honest. My days of probing & figuring men’s faults out are (hopefully!) over!