Should I ask this man on a date?

[Idontknowhowtorelationship]

So I really am not sure how to handle this and it is difficult to to talk to anyone in real life as they know the people involved. My brother is married, his wife is lovely and she has a brother. He is single, the same age as me (both early forties) and is a lovely man, he is always kind, caring and listens, he is great with my brother's kids (niece and nephew), head screwed on with work, owns his own place etc.

He is largely single because he has focused on his career, building his own business, I have been very career focused but I will also admit I also have had awful choice in men, I tend to go for exciting, or at least what I think is at the time, which normally means dysfunctional, a bit unstable and they end up not treating me nicely (cheating, hiding debt, using me for money etc.) In that respect he is the total opposite, an all round lovely guy. We have always got on well (12 years) and there has always been a little bit of casual flirting, but nothing that would have ever gone anywhere and I was usually in car crash relationships anyway, he never made a move, he never said anything over a line, just slightly cheeky on occasion when I pushed or teased him a little.

Anyway I had not seen him since Christmas but last weekend we were both at a family event, he had a few family health scares and so has decided to make a lifestyle changes and improve his health. I knew about this from my brother but I thought he was slightly overplaying it. I walked in the door and my jaw actually dropped, he has gone from overweight but still attractive (he was in many ways even when he was on the edge of obese) to some kind of athlete, lean, toned, absolutely gorgeous, he was playing games with the kids and when they were doing handstands against the wall his t-shirt fell down, he has a gorgeous six pack.

He came over and said hello, gave me a hug, usual friendly greeting stuff and I felt something I have never really felt about anyone before. It has been a week now and I still cannot get him out of my head at all, he is on my mind every few hours. I have messaged him a couple of times, we tend to message every couple of weeks, he is really good at giving me advice for work when I ask, but I keep feeling like his messages are flirting, even though if I try to read them objectively they are just being kind and helpful. I know we get on for sustained periods as well as he babysit my niece and nephew for a week, it was originally supposed to be a two day stay but travel disruption messed things up and my brother and sister in law ended up stuck abroad for a week, I went to see the kids and stayed for the weekend in his spare room, I realise now it was a little bit of playing happy families when he looked after the kids and me (worked, school run, cleaned, cooked dinner every night, did the kids laundry etc.) and I floated in over the weekend and was looked after.

I have never felt this way about someone before, maybe it is having known him for years but now being single and realising that he is super hot it sort of all mixed together. It is not my biological clock, I can't have kids, but I do recognise that after all my bad relationships he is kind, caring and in a relationship sense safe, he would never cheat, he is kind, he would look after me (in a human way, money wise we both earn six figures so that is irrelevant).

Is it too close to home, is it just looking for the nice guy and I will still mess it up and end up hurting him, am I genuinely interested in the nice guy for once, or will I screw it up?

I realise that is a lot of waffling, sorry!

How interesting. Life is too short. Anyway can you force some meetings together? Maybe even get a discreet relative involved. Say you see how he has changed and looking good. Most women would pick up on this. Don’t bother with any man for help with this. It will go right over their head.

There are quite a few family things over the next few months that will both be at, but they will all be lots of a family there so I don't really know. Slightly annoyingly there was potentially one that would have just been me and him babysitting for a day and overnight if I could have gone, but I am at a friend's wedding, as a bridesmaid, again.

The only people close enough in that respect would be my brother (who has little emotional intelligence) or his sister who is lovely (my sister-in-law) and I feel that would just be weird to ask either of them.

"Hi Jim, I really want to go and see XXx, but no one else is interested, dont suppose you are?"

Ooooohhhh OP I like the sound of how well you already know each other and the trusting relationship you have. That, plus the six-pack, must be a potent combination 🤩 Offering to take it to the next level is risky, though, because he's so closely related. Do you have the kind of relationship with SIL/DB where you could casually suss them out on the matter? I don't mean seeking their views or judgement, but if you were to say something like "OMG I'm seeing him in a whole new light" it might be interesting to see whether their reaction is "Oh god don't be daft" or "He's always had a thing for you." But if you sense there's always been a bit of flirtation between you, then there's no need for that -- you should trust your gut and see what happens. Good luck!

He is lovely, I know he is genuinely lovely, that is the problem. I tend to go for men who are broken in one of several ways, they are usually bad with money, they might cheat on me, sort of a little bit bad boy, I think I can fix/tame them and it all goes wrong. He is so kind that I feel I will be trying to subconsciously find a way to mess it up. Can I actually do a relationship with a decent man?

My brother would take the piss out of me for having a crush on "Jim" (borrowed from the post above), my SIL I would just feel weird asking in any way (I want to have sex with your brother).

At the family event, it was family but also a lot of their (Brother and SIL) friends and I think everyone was seeing him in a different light, a few of their friends have got divorced over the last few years, a few were single, even some of the married ones were enjoying a good look! He just seemed to take it all in his stride, not bothered in the slightest. I know when we have talked in the past he has never seen himself as attractive and I am not sure even now if that still impacts him, despite being good looking, successful and very kind he has always had self esteem issues when it comes to women. In the past I have always said that everyone feels like that sometimes and he is a lovely man, but now I want to drag him to bed and prove it to him! I do also wonder if part of that is perimenopause the dragging him to bed bit, not finding him attractive.

I have just had a call from my sister in law about organising something else for my parents, I asked what they were up to this weekend and she said something along the lines of "Oh, we are off to Jim's, it has been a hectic week so he has said to come over and he will cook us a roast dinner for lunch". After the call I just kind of said to myself "Please can I come", it makes me feel a little pathetic, like some kind of love sick puppy, or a twelve year old.

For ease, I will use "Jim" for this tread, much easier than trying to figure another way to refer to him!

This could be an idea, I just need to try and figure out what it might be, I know he goes to quite a bit of live music but he books that up as soon as tickets come out and I don't really want to just pick something random that it is going to be obvious that I am not interested in, I guess I need to get thinking!

No. Too close to home.

So if you are suggesting something to go to (and no one who wants to go) it needs to be something soon.

Local theatre or cinema comes to mind. I have just booked to see Kenneth Branagh at the Royal Shakespeare Company but it’s next June so that is why although it could be tempting for someone it’s ages away! I don’t doubt that if husband doesn’t want to go at the last minute I will find someone else but it’s next blooming year.

You need something within the next 10 days maximum!!

The other thing is you just might have some competition. Get in quickly and at least you will know.

Does he go to live music on his own? It sounds like he is comfortable doing this. Or show great interest in live music and call him and say you are looking to expand your interests and you remembered that he likes live music. What could he suggest that you do next to expand your knowledge…..

I don't think you should just assume you can't have a relationship with someone who isn't an arsehole. I landed on my feet eventually with a kind and loving man after some absolute shithead horrors for decades. I think I was just passively accepting them because I had low expectations generally. It is a million times better being with a decent human being, and I guess the six pack will help 😉

This is very close to home. If it doesn’t work out you’ll likely affect what seems like a lovely close family set up where you get together regularly. Think carefully about the possible repercussions.
It’s also interesting that you’re only this keen now he’s lost weight. He might look good now but will you still fancy him as you both age and he might put some back on, if it’s the physical side that’s prompted you to feel like this?
All that considered, if you really want to go there I agree you probably need to make a move fairly quickly as good men don’t stay single for long. He might already be dating.
Ask him to do something just the two of you and see what happens.

I would be extremely cautious. If you do get into a relationship with him and it doesn't work out, it could well end up in a difficult and awkward family situation! I'd feel sorry for your brother and sister in law, they could end up feeling put in the middle of a break up and each taking their siblings side.

I'd say way too close.
If this goes wrong then it can have massive implications on an entire unit and for me it would not be worth it.

You're only thinking like this and wanting to make a move now he is physically attractive to society. I think if you really like someone then you fancy them due to what's inside. Sometimes this is initiated by their physical attributes and you get to know them more after because their looks draw you in, but considering you've known him a long time you would have been at this point way before he "got hot" if this was a deep attraction.

Marry him immediately.

To be crude, don't shit where you eat.

This could go horribly wrong.

She hasn’t noticed him when he was overweight. I wonder what would happen if the six pack disappears

Me and DP actually know 2 lots of siblings married to siblings!

First is a couple I know from work. They met in work, and started dating after a few months. At the same time completely coincidentally her brother met his sister in a night club and hit it off! Took them a couple of months for them to realise that they were all going out with each others siblings!

Second set is a more similar situation to yours @Idontknowhowtorelationship , DPs friend met her BILs brother as her sister and BILs wedding approached, they really got on. After the wedding both ended up asking their siblings if they'd find it too weird if they asked them out (this is really hard to explain coherently!). Everyone was fine with it, so all good.

In both of the above cases, everyone is still married and happy 10 or more years later. I know DPs friend sometimes feels like they're all a little bit too enmeshed, as there's no escape to an alternate set of in-laws every Christmas for example. It's also slightly weird now they've had kids, how much they all look alike, as despite being cousins they're actually genetically siblings!

I'd say go for it OP, although I'd talk to your brother and SIL about it first, make sure the idea doesn't weird them out at all. It's fine if it all works out, but I'd imagine if you then break up it could end up being awkward for them!

Go for it! What have you got to lose. As long as you’re both mature if it doesn’t work out so it doesn’t impact on your family.

It does kind of feel that way though, I had some therapy sessions earlier this year, death of a family member, every relationship I have been in has been with an arsehole, but I look back and I have consistently rejected good, decent attractive guys and chosen the arsehole instead. I realised just how bad most of my previous relationships have been but I also realised it is not all men, it is just that I seemed to go out of my way to pick arseholes.

He has always been a lovely man, as I said in the earlier post attractive even when overweight before, but yes he is absolutely gorgeous now. This is the first time I have met him whilst single and yes him being physically in amazing shape does help, but I also did therapy earlier this year and have now been single since Christmas (I dumped my last car crash ex after he cheated on me between Christmas and new year) and it is one of those things that I also think he is a lovely guy. I think even if he was a bit overweight he would still be attractive.

I think it would be ok if we did split because I imagine it would be civil, rather than him cheating on me, stealing money, treating me like shit etc. because it is very obvious that he is not that kind of man. I also think he is amazingly attractive now but equally would be if he was not as trim as he is now, or even a bit overweight.

My bigger issues is really me, he is lovely and I wouldn't want to hurt him, he has been single for fifteen years (he focused on building his own business) and I have been in thirteen relationships in that time that all ended badly because I picked awful men in that time. I had some therapy earlier this year and it has made me question some things, but also the last few days I have been thinking why am I looking for someone totally different to all of my previous partners. He is essentially the perfect guy (at least for a woman in the 30-45 range), attractive, successful, financially sound, kind, caring, good with kids, looks after his family, that is pretty much the opposite of what I usually go for, they were always attractive, but not good in nearly every other way.

I would like to think I am quite attractive, I have a good career, am financially sound myself, but I am also questioning if he would be interested in me when he could easily have the pick of most single women out there, someone probably equally successful, more attractive and younger than me. Or that because I have only been in awful relationships I will somehow push that onto him.

There are five family events over the next two months and then more around Christmas, I don't think I will force it or do anything just the two of us, but maybe just try to see how I feel meeting him those times and how he might react to a bit of gentle flirting, nothing that cannot just be dismissed as friendly fun if it is not well received and see what happens from there. I need to question my own motives for finally wanting to go after someone decent, I really would not want to hurt him.

When you get chatting to Jim at the next family event just say that you really miss going out for a meal/to the cinema with a man instead of girly chum or family nights.

He sounds great OP and I don't see why you wouldn't very very cautiously go for it. Is there any way you can engineer some time just the two of you together? It doesn't have to be a big formal date.

Could you text him "hey, I've an appointment in your neighbourhood next week. Do you fancy meeting for a coffee afterwards? I'll be free from 2... "

Leave the day out (accidentally). Because if he says "great, what day - I'm around except Wednesday" you can have meant Tuesday. Whereas if your pretend appointment is on Wednesday you've snookered yourself.

At the end of the coffee non-date "this was lovely... We never really see each other away from the rest of them... " and see if he takes the bait.

Don't mention any of it to mutual people. You want to see if there's potential there without extra pressure.