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 was thinking that first story was so mad when I remembered in my twenties I bumped into a guy from the year ahead of me in school. He was chatting me up at the birthday party of a mutual friend not realising who I was. Mutual friend said my (very unusual) name and he looked totally taken aback. I said (I was brave in those days) "oh please don't stop chatting me up" he laughed, got my number and we were away.

On the very same night my best friend was on a crap night out where all her friends left her and she thought f them and went to a nightclub where she met a very hot guy who lived locally to us apparently - but nowhere near our nights out.

We were keeping each other well informed of our blossoming romances over the coming weeks and, very excited to show off our new beaus, engineered a date where we could 'bump into' each other. We both arrived exactly ten mins late deciding we'd walk in together pretending we bumped into each other outside as we knew if we had to fake the chance encounter in real time our poor acting skills would let us down.

Well imagine our confusion when we found our two new men - looking VERY similar seated at the same table waiting for us.

Don't be daft. It will be awkward as hell for the whole family when if it all goes wrong. Plus, a man who hasn't dated in 15 years doesn't sound like he's interested in dating at all.

As a random on the internet - I really want it to work and cheer you on, it sounds like a rom-com and you deserve happiness. But from what you’ve said about both of you, it’s reading as a mismatch, too big a risk and too close to home.

And just for a bit of balance, I’d also be inclined wonder if there’s some other reason why he’s single. There is no such thing as perfection, everyone has their issues. The key is either getting to grips with it, finding someone who has no issue with your issue, or maybe even likes it (!) or has the will to be with you despite that.

I know you said he’s been building a business but IME women further motivate men with a plan in place rather than hold them back. I barely know a self-made man of that age who hasn’t a woman at his right hand. In fact, if dude is facially handsome, pleasant, kind to kids, successful and driven, I’m stunned he’s not been nabbed. Him previously being a bit heavier than some would not matter to a lot of women either. Maybe he really has got some self esteem issues - that could make him a tricky man for you to be in a relationship with - or perhaps there’s something else. He might be asexual. He might have some other sort of hidden dysfunction. Who knows? Not me! You don’t necessarily sound like nurturing someone with self-esteem issues is a good fit for you romantically. That’s not a criticism. I’d find it a total turn-off no matter how he looked.

Obviously I don’t know you from Eve so you probably should disregard this because running that risk is part of being alive, we don’t want to die wondering ‘what if.’ It’s just your description of you both makes me think ´careful now!’ Then again, maybe you’re being unfairly critical of yourself. Perhaps that’s why you keep picking wrong ‘uns who don’t deserve you. And now you don’t want to end up being the wrong ‘un. I really empathise with that.

Hmmmm I really want this to work out for you, but I do have a couple of niggles now.

One is that he seems to have kept his own life scrupulously stable. If your romantic life has been so chaotic (I say this without judgement... my own was car crash entertainment for decades!!!), then he might be wary of getting involved with you even if he fancies and likes you a lot.

The other thing is you saying "I think even if he was a bit overweight he would still be attractive." I wouldn't have batted an eyelid at this before meeting my now-DH, but we would adore each other even if one of us grew another three heads or lost a few limbs or doubled in size. If you don't feel that much love for him after knowing him all this time, it sounds as though he just ticks the right boxes on paper and part of you wants to learn how to have a "sensible" relationship.

Not sure OP, honestly. It's a risky experiment... although like anyone I love a Christmas romance so am half hoping you will ignore this advice!!!

I do find it strange that he is successful and lovely, and now more conventionally attractive too, but he still doesn't date at all. Has he ever discussed why not? Has he ever had a longer relationship, perhaps when younger? It doesn’t sound fair to think so perhaps but it does make me suspicious

Sounds romantic & exciting! But I think if he were interested in you, he would have made a move in those years. Don’t fool yourself - you are crushing on a man who may be making himself unavailable. Too risky!

He has self esteem issues, he has done his whole adult life, one thing we bonded over in the past was that our respective parents messed us up in different ways. His were very critical of him, always pushing him, no matter how well he did he would never be praised, but his sister (my sister in law) got praised for trying regardless of how well she did (she and he have talked about this, they both recognised it was toxic for them both as kids). My sister in law commented earlier in the year how he just seemed to not realise when someone was hitting on him. We talked a bit at the family event the other weekend, it was a drinking event, we were helping clear up at the end of the night but chatting just the two of us, mostly talking about work but touched on some family and relationship things. His job means he deals with incredibly successful people, people who earn seven figures a year, people worth hundreds of millions, deals with senior people at very large companies and he just is not bothered about it, take it all in his stride (he was not boasting, just being honest, my sister in law says he is like that), but that in personal situations he struggles. Two days before my brother and sister in law got married Jim was presenting to the senior management team and VPs of a huge UK company, took it all in his stride, not bothered in the slightest, at their wedding he did a very short speech, he was incredibly nervous before, said his heart rate was through the roof, terrified. I asked him why and he said (slightly paraphrasing as I cannot remember exactly what he said) "In work I know what I am doing, I am there because people want me there, worst case is I don't get the business, it doesn't matter. At the wedding it actually mattered and I have never really got people socially".

He had some shorter relationships when he was younger, I think in his early twenties he had no shortage of women interested, his last girlfriend cheated on him and so he dumped her right before he set up his business and he has been single since, I don't think he coped well with that and buried himself in work.

There was an interesting chat with some of my sister in laws friends when we had all had a few drinks when we said how good he looked. One of her friends who she has known since they were at school said that he looks amazing now and still doesn't realise it, that he looked good when he was late teens and early twenties but never seemed to realise it then either. She said her friendship group had always said he was the kind of man women want when they get divorced from the bad boy, they think they want the fun and excitement of that bad boy, but most women grow up and ultimately want someone kind, caring, stable and loving. Earlier in the night she had spoken to him about how much work he must have put in to get fit and he had said something along the lines of still having a long way to get as fit as he wants to be. He has a six pack, he runs 10k most days and could pick me up with one arm, how much fitter could he get?

I have actually emailed the counsellor I had therapy with earlier this year, I think I need to figure me out first. Even if it is not Jim, am I now capable of having a proper relationship with a fully functional human being, a nice man, or will I just end up craving someone who I find "exciting", but who ultimately treats me like shit. I would need to be sure first because even if I did go down that route it is not fair to make him be my experiment as he is such a kind man I would not want to hurt him, I don't want to be the arsehole to him that my last 13 boyfriends have been to me!

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

This

I read a few days ago about a (married) woman who had similarly lost weight and she was quite irritated by the way she now had people talking to her, looking at her, basically experiencing a different side of life. She said she was the same person and didn’t like that people saw her differently. I can imagine this man might think ‘I knew her for 12 years and she never led me to think there might be anything. Now I have a six pack she’s showing her shallow nature’.

In life, always go for it, make the move, do the phone call, apply for the job, approach the person. But be prepared for a ‘no’.

He sounds truly fab. But his lack of relationships would concern me. He may not be interested in meeting someone in which case you would have to pursue and that wouldn’t make me happy.