Leaving the past in the past? Or not?

[Uncertainandconfused]

So here goes. About 18 years ago when I was (obviously) a lot younger I had a fling with someone I liked very much. To be honest he was on and off between me and another girl. It was all very hurtful at the time. She got pregnant and he ended up with her. I still saw him on and off for a few years after that as they were on and off too. Altogether not ideal I know.
Anyway time ticked on, I settled down, he settled down. Life happened, ups and downs, no contact for around 10 years or so.
I’m single now after a couple of longish term relationships. I’m also now older and wiser. His relationship has broken down. He kept asking me for advice (work related). I’ve been putting off and putting off meeting up. Anyway recently we did. I gave him advice, we had a good chat. I enjoyed it. I was happy to leave it at that but he keeps messaging me, he wants to meet again. His relationship breakdown is very recent. I’ve told him I want nothing to do with it. I’m not getting embroiled in someone else’s mess. I’ve had enough of my own to deal with. Part of me is also thinking I don’t want to be a rebound fling or a back up plan. But having seen him again feelings were still there. Now I’m totally confused. He hasn’t treated me that well in the past although I allowed that to happen. I’m tempted but my wise old head tells me to stay well away from this. But my stupid heart is wondering if this is (finally) our time. WWYD?

Just to clarify I haven’t hankered after him for all these years. And I’ve been trying to keep him at arms length since he got in touch. Arghhh

Walk away. You are worth so much more than him.

If he didn't want you the first time....

Stay away!

People can change a lot in 18 years especially if they were fairly young 18 years ago. It might all go pear shaped again it might not. It depends how much you like him and how resilient you are as to whether or not it's worth giving it a go. All relationships are a gamble, but being on your own gets boring.

OP - you are both single. And as you say you are older a wiser.
So, I presume, is he.

18 years is a long time. And people do change. Him not ‘picking’ you back then doesn’t mean you are a ‘back up’ now.
It’s more that you share a history and there is something nice in that familiarity.

So - what do you really have to lose? Meet him, have fun, see how it goes? You said it yourself - some feelings are still there.
And - as you are now older and more self-aware - you can leave at the first warning sign.

Thank you for your advice. He came and met me out with my friends Saturday unexpectedly at his request (they all get on anyway). Had a laugh with us all. He keeps messaging me since then and Ive agreed to see him this weekend. I’ll admit I’m struggling with trying to figure out what is going on. He seems keen and I do like him (if this was happening to the 24 year old I was when I met him I’d be overjoyed!) I think we need to have a conversation about what he actually wants. I’m keeping him massively at arms length emotionally and I think it will take an awful lot to get past that. It’s niggling me that his relationship breakdown is so very recent (about 3 months I think). I’m 42, I’ve been through so much in the last 2-3 years with my own LT relationship breakdown then only about 3 months ago another break up after 11 months or so. I’m tempted to just go with the flow but keep him at arms length. He has lots to sort out with his ex still and I want nothing to do with that. I trust him as a person but not as a partner, he’d have to earn that. Half of me wonders whether to just leave it but with such a long history it is tempting to see what happens. I feel very conflicted right now. He’s chasing me (not obsessively) which is a total reversal from the past. WWYD?

Honestly ...
I'd walk away, but I don't think you will.

What would be your reasons Sandy? Out of interest? His past behaviour? His recent relationship breakdown? It’s all going round in my head. I think I’m a strong woman and in the right place emotionally to walk away if I sense any alarm bells when we’re together. I hope I am anyway

WWID?
As I (you) haven't been hankering after him in the meantime, and I'm feeling wary now, I'd tell him to cool it for a bit and get himself sorted out re his ex etc, before I even thought about getting close to him.

Hi mxy, that is what I’m thinking tbh. Thank you

I'd walk away.

He messed you around before, he's obviously not averse to doing that to someone, or you again.

My reasons would be the past behaviour and the fact that he's still got stuff to sort out with his Ex.

At this stage...I'd rather avoid the drama.... however... if you're able to not get emotionally involved and okay with just a physical fun fling... then maybe.