Could this be something real after 20 years?

[Coulditbesomething]

I have a friend I’ve known for 21 years. I met him at uni when I was 17 and he was 18, we’re now 38 and 39.

When I first met him, I really liked him but was painfully shy, so I never said anything. We spent time together doing classwork, chatting in the library, exchanged numbers… but nothing came of it. He soon met someone who became pregnant, and we lost contact for a while.

When he was 20, he got back in touch, he and his partner had split up. We met up, kissed, dated a little. I was still shy, and at that age I didn’t feel ready for a relationship with someone who already had a child, so I held back. Things fizzled out.

A couple of years later, we reconnected again, same story. We dated, kissed, spent time together, but neither of us expressed deep feelings, even though I was secretly crazy about him.

There were a few times when we would bump into each other on nights out and would end up back at his parents house - but we just talked, and kissed and he would drive me home in the morning. I always knew how much I liked him and I think thats why i never slept with him, i was so scared he would break my heart.

Then he met someone else, had another baby, and our contact became very occasional, always platonic. After that relationship failed he contacted me again and we had a night together - we didnt sleep together but it was a great night, i dont remember who stopped contacting but either way - it fizzled out again.

I later met someone myself and was in a 14 year relationship, and he also settled down. Over all of the years we stayed in touch via Facebook messages and texts, purely friendly, chatting about life, kids, relationships, offering advice, wishing each other well.

My marriage has recently ended (not my choice). His long-term relationship has also ended (not his choice) they were together for over 10 years and have a 1-year-old.

Since we’re both single, we’ve been talking a lot more than usual. There’s been some gentle flirting and talk of meeting up. He has three children (21, 17, and 1) with three different women. I have two children (10 and 8 with my soon to be ex husband). Our lives are complicated.

I don’t know if I’m kidding myself that something could happen after all this time. He hasn’t said he wants a relationship, but he often talks about “what could have been” and wonders what might have happened if things had gone differently.

I do like him, I’ve always liked him, but I also know we’re both coming out of major breakups and have a lot going on. I'm in no rush for anything. I'm not interested in filling a void, im not interested in being a rebound either. But I also know that there have been quite a few missed opportunities over the years and I don't want to waste another 20 years wishing I had told him how I felt.

Has anyone else been in a similar situation where a long term friendship turned into something more after years apart? Did it work out?

So he's had 3 children with three different women and the youngest is now only 1 years old? He's also had lots of casual sex? He sounds a great catch OP.

@cloudtreecarpet yeah we used to say these things to each other when we were much younger, early 20's. I cant remember when the book was published but probably about 2009/2010 - Once I met my husband, we didn't say things like that anymore. We haven't even flirted with each other in that time - im not like that - i loved my husband. I would never flirt or lead someone on, or try to get attention from another man.

It's only since both of our splits that things have been flirtatious and it has made me think about all the things from the past and the way we have been there for each other over the years and wonder if there is anything real there.

I was thinking today about if I didn't know him and he was a stranger on a dating site for example. I would instantly be attracted to him, I know that, because he is an attractive man and still looks great. But If I read that he had 3 kids to 3 different women with the youngest being 1...I am not sure I would make contact with him to be honest. In fact, I know I wouldn't make contact with him.

But in saying all of that, i know all about his baggage, and he knows all about mine, I know so many things about him that are so much more than the amount of children he has or with how many women. He's a decent man. Maybe on paper he doesn't seem decent or good, and some of his choices are questionable - but i do think about him a lot just now.

If a friend came to me with this exact same scenario - I won't lie, alarm bells would be ringing for me, so i am appreciating getting different points of view, it helps me to see things in a balanced way instead of jumping in and ending up being disappointed. x

@ginasevern in his early 20's he did have lots of casual sex thats true...had a few short term relationships and then his last relationship was around 10 years...maybe a little more than that.

I do want to be honest about him and not hide things because I would rather people gave advice on the whole picture - its easy for me to skim over things...so its good to get views about the bits I might gloss over x

He may have been a significant constant in your life for years but there's never been any commitment which is much more difficult to sustain. I'd say keep him as a friend only, especially as you have no idea how he feels about you.

Completely agree with this. His track record isn't great as he tends to have jump into relationships, have a baby and then it ends.

Leaving a 1 year old is a red flag, since this is the 3rd time!
My prediction - you'll end up hurt but perhaps you need to get it out of your system and finally understand why all 3 serious relationships have ended. It might help to remove your rose tinted glasses.

I think you are his back up girl, he will have known you liked him but we're never "the one".

I do wonder if because your marriage just ended the idea that maybe this man was the one you should have been with is dominating your thoughts more.

Does the romantic idea that you & he were really meant for each other make the end of your marriage easier to deal with & to understand?
Having been through it I can definitely understand how someone from your past emerging in a semi-romantic way would be so appealing & comforting at this time.

But I just think you are vulnerable right now & could easily make a bad decision
Be honest with yourself - are you really over the end of your marriage which you say wasn't your choice?

Honestly, no, im not over my marriage @cloudtreecarpet Im still really sad about it. But i've been sad every day for months and months, i could spend the rest of my life being sad about it if i allowed for it.

I don't think i should have been with him this whole time though. I have 2 wonderful children, and I really, really loved my husband. I'm so sad my marriage has ended, but I am not sorry or sad it happened. I would make the same choices over and over. But that's ended now - there will be no reconciliation, so im trying to make choices for my life that make me happy and i dont want to draw a line in the sand and not explore that option. I think thats why this forum is so wonderful and so helpful, it's good to get different perspectives and to consider things in ways i hadn't really thought about.

It's helping me to see that there are 100 reasons to quietly walk away, but I think im going to allow myself to be open to the possibility of things going somewhere.

Maybe nothing comes of it...but I would like to think that when im an 80 year old woman that I can say that at least I gave it a shot and i got the answer - no matter what the answer may turn out to be x

Ok, well, good luck, I hope it works out

Obviously it goes without saying to not involve the kids on either side until you are really sure...

He doesn't sound much of a catch OP, sorry.

If your marriage break up had not been initiated by your husband would you have broken it up for this guy?

Op, just want to say you come off as a wonderful person with sound morals, a big loving heart and a willingness to hear others. I think you are doing the right thing by staying open to the possibility without moving it forward. I think it would help to keep the thread updated as things move forward as it might give you a place for perspective that you - being so close to the situation- might not have. Wishing you luck and healing! 💐

@Coulditbesomething Look - personally I think you only live once, and better to try something than regret never trying.
You have done the dancing around; the getting married/having kids + marriage breakdown.... What exactly are you scared of now? You have already survived something really terrible and are (will be!) OK.

So - this will not break you even if this turns out to be nothing. You are not an impressionable 20yo whose heart will be broken into million pieces... You have your kids to ground you. And he is but a man....

Personally - I'll give this a go and use it as a way of healing, as you are going through this difficult time. Don't put some massive romantic expectation on this (hard as it is to avoid these movie references)... And don't think that you are some sort of cancelation prize for him - men, even those with small kids have no trouble finding women to date. Women not to much, but it's a different discussion...
I'd probably sleep with him sooner rather than later - as it is you already put so much importance on NOT doing it in the past, that it snowballed into an even of huge magnitude. And - I'd remove this unnecessary hurdle and just tried to enjoy getting to know each others as grown up adults...

I think you are doing what you've always done with this man, overthinking, rationalising, procrastinating. Be brave and go for it. Tell him how you feel. Yes you may get hurt but thats always a risk.

The thing is, you have to take risks. Even if a man tells you he's not into casual sex he could still end things after sleeping with you one time, 5 times, 25 times. There are no guarantees.

You are his back up when things don’t work out with someone else. This screams 🚩 to me, sorry to say. Think wisely before you take things further.

I suppose if u don't try it you will never know. I would be reluctant to get involved with someone with a 1 yr old, particularly as you are past all the early years stage. I would keep all children apart. If u could explore where this is going and coordinate seeing each other when his child and your children are with the exes, this would be ideal i suppose. 3 children with 3 different women though- complicated 🙄

Sorry, I’m another one that thinks his heart’s not really in it. You’re obviously a lovely person - very reasonable and understanding everything from everyone’s point of view and very fair about the women in his past relationships. I’m sorry to be so harsh but I wonder if all this reasonableness comes across as a bit bland and the spark just isn’t there. You’re a safe back up when he wants someone.

@bubzie No, never in a million years. When I got married, I believed it would be forever. It's only because my marriage has ended that im even entertaining the thought of something romantic. I have not sat for the last 15 years wishing i was with this person, or any other person. I loved my husband...its only very recently that ive started saying 'loved' instead of 'love' because he has moved on. He cheated, left me for her, now lives with her in the home we bought and lived in together while raising our family, so its time for me to let go of my marriage and move on with my life too. I would very much like to have a romantic partner in my life and that can be a stranger - or it can be with someone who i know, trust and who has been nothing but kind to me for years - decades really.

It might not go anywhere, but what i have realised is, it might not go anywhere with a stranger either. You just never know. So yes, i risk losing him as a friend if it turns sour, but life isn't a dress rehearsal and I would rather take the chance and know the outcome than to always wonder x

I totally get where you’re coming from but tread carefully. This man clearly has a bit of a reputation of not sticking around. He has 3 children to 3 different women. What part does he play in their lives?

Protect your ❤️. You sound like a really nice person. Don’t allow yourself to get hurt.

@TulipsTwoLips I think i am a bit bland to be honest. I don't think i always was. But the last few years have taken a lot from me. My energy, my time, my trust, my personality. I'm still healing and trying to figure who I am now x

He got 3 women pregnant, doesn't seem the shy type to me.
I think you're ronanticising the situation OP, I don't think it'll work out.

Given you’ve both had times where you were both single and haven’t got together I don’t think this has legs OP. Sorry, but it would’ve happened by now. Objectively he doesn’t look like a good prospect and I think it’s all too tempting to view romance like a film but the truth is it just isn’t.

Time for some you time I think 😊. Go find your spark again lovely lady - you can do better than him!