Please set my head straight

[Rockall2]

I feel silly writing this but I am
quite sure that my head is muddled and I need some perspective.
I have recently reconnected with an old friend from my school days. We always got on well and kept in contact for a while despite him having moved abroad. There was definitely some attraction back then but we were always quite different and on different career paths, and we eventually lost touch.
He has now moved back after 20 years abroad and he has reached out and we reconnected. At first I felt happy because it felt like old times but something has changed and we have started seeing each other now.

Part of me knows that there are probably some red flags and I know that I’m not always recognising them for what they are:

He’s divorced twice and has two children who he doesn’t see often (his own words). I know that he can charm the socks off anyone if he wants to whereas I’m quite reserved. He’s definitely a risk taker and again quite the opposite to me but I find it very exciting and refreshing if this makes sense.
I know that I’m 100% smitten but I’m afraid that I might be missing warning signs and that I’ll end up getting hurt. I don’t want to sabotage this either though. Any tips how I could gage this and what I should be looking out for?

What are you looking for OP ?
If it’s friendship and having fun he sounds like he could make you happy .
If it’s long term commitment no one really knows what will happen?
You don’t say what your circumstances are, do you have children at home etc are these the possible red flags you are referring to ?

Oh I am hoping for a proper relationship. My concerns are if we are too different deep down (he’s done a lot of wild stuff whereas I am Mrs Cautious). For example I remember calling him while still in uni because I had been offered cocaine and I was curious and terrified at the same time and he was the only one I knew who’d dabble. Of course I didn’t take it because I was too scared.

I don’t have any DCs myself but I was a bit thrown by him not seeming to care much about his 2DCs. I have 2 DNs and I can’t imagine anyone in the family not wanting to see them, let alone their parents.

Yes, not seeing his DCs and especially not caring about it is a massive massive red flag if you want children with this man.

can you get to the bottom of his feeling on the matter? Is it something that was forced on him and he’s absolutely devastated not to see them all the time but underplays it?

Just be open and honest and direct.

tell him the truth and ask what exactly he is looking for and voice your concerns.

I don’t think it matters what someone has done in the past but it does matter that you somewhat match your current lives

Does he still dabble in drugs? Drink excessively often? Because that’s not someone who will be a life partner. It might sound fun now but it won’t when you’re living together and he goes out drinking and leaves you home, or spends his money on drugs rather than bills.

Do you want children in the future? Because he’s proven he is not a committed father to his current children so I definitely wouldn’t be considering him as a potential father to my future children.

Has he been open with you about why the divorces happened? Why he doesn’t see his children?

He doesn’t drink a lot, but he said that he does take drugs occasionally when he gets with specific friends.
Yes of course I have asked about his marriages. Apparently one is “crazy” (I know…) and made access to the child difficult as soon as they broke up which is of course possible. And the second one was rushed because she got pregnant after less than a year and apparently they were fighting about everything. He sees the child more than the first one but not often. They are in a different country so now it’s obviously more difficult to see them anyway. I just still find it strange and a bit sad

I would find a man not seeing his children deeply unattractive and a huge red flag.

Whatever you do don’t get pregnant by him..

OP please read your first post back to yourself and ask yourself what would you say to a close friend, or one of your DNs if/when she was old enough, who was telling you this about a man she was involved with.
Personally, I can see several red flags📧

1. Divorced TWICE!
2. 1ST EXW was "crazy"? Oh dear, no!
3. He "dabbles" with drugs , cocaine??, when with certain people? As the STBXW of a cocaine user, who developed a problem with it due to spending time with certain people, this makes my alarm bells CLANG!
4. He married the 2nd EXW in haste, before they knew each other that well, because she was pregnant? It's not the 19th Century! I don't buy that TBH and think he's not telling you the whole truth!
5. He hardly sees his children?? Oh no OP! That's a scarlet flag! Swerve!
6. To sum up, he's impulsive, prone to high-risk behaviours ( cocaine is not just highly addictive, it's dangerous!), he's failed at not one but TWO marriages and worst of all, he hasn't been a committed, present father to his children!
7. RUN!!!

Op, you started this thread because you know this isn't the man for you, you're just wanting us to tell you that "everything's fine, nothing to see here" so you can keep seeing him. It's not fine. This man is a walking red flag.

Be sensible and don't get caught in a trap where you wake up one day and realise you've wasted too much precious time on a man you knew wasn't suitable from the start.

I’m sorry to burst your loved up bubble but he is a walking red flag. You’re not missing the warning signs, you can see them as you’ve said yourself you question some of his choices, but if you continue to see him then you’re choosing to ignore them.

You deserve better.

Yes I can see the flags but I wasn’t sure if I was self sabotaging because I have a tendency to overthink and im
probably a bit too cautious at times. Thank you

Any tips how I could gage this and what I should be looking out for

The whole list of things that you need to look out for in a potential partner will be clearly detailed to you by your feelings. We don't know best. You do.

Things like disrespect, mocking you, spending your money, insults, violence etc that can be found on 'red flag' lists will all make you feel uncomfortable. That's the red flag. It comes alongside things like 'incompatibility' (i.e. it makes you feel uncomfortable that he goes clubbing until 3am every night, when you like to get up at 6am, or it makes you feel uncomfortable that he plays computer games all the time whilst you try to have a scree-free life) and 'not understanding you' (i.e. you tell him you want to talk about feelings and he says 'I feel hungry')

You gauge it by working out how uncomfortable you want to be, and working out if he's getting it right, according to your preferences.

The fact that you're asking a forum suggests that you don't self validate. Give it a try. It's life changing.

I understand what you’re saying, I’m also prone to keeping myself up at night overthinking. But in this case your caution is justified. I hope youre okay because it’s hard to admit something you thought could be long term actually isn’t, but it’s making space for you to move onto something better.

It sounds like he makes you nervous, so I'd be very careful. You don't sound particularly compatible, but sometimes different is good. I wouldn't judge him for being divorced, or occasionally taking drugs, but you may feel differently? With his difficulty with keeping in touch with his children, this is relevant if you want kids. Sometimes an ex is actually crazy though, some men seem to like that type. Just judge how he treats you, if you really do like him. People can change as they grow up.