One giant leap forward! - Part 5

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The car insurance and the kids at the weekend are going pi55 her off but not much she can do about it. She can just say no to the driving, then what?

You really need a mediator, or a lawyer, and you need to get a specific agreement in place and filed in family court. There is no reason all of this responsibility should fall on you.

Not me, it tears me up inside. I have always had a problem with the fact that I haven't lived the life of at least an ordinary single man in his twenties.
I haven't experienced enough life myself as a single/dating person to be OK with whoever I end up with having done so themselves.

This is something I can tackle now and hopefully put me in a better position in the future. I don't want to be a 40 year old man that is jealous of his current partner having had sex with more than one person in their 20's. It's not healthy and eats away at myself and the R.

I don't expect people to understand where I am coming from.
I feel like I have a second chance at enjoying some dating and learning things about myself and I don't want to miss it.

Dating 100 different women will not change the fact that you are a jealous person. This is something you should address in counseling to understand it. After you do, go date to your hearts content. We aren't saying not to date, but T, regardless of your intention to 'casually date' here is how it goes: you date, maybe a few people, then you meet someone who you really like spending time with and before you even know what happened, you are in a R. Then, because people haven't done the work on themselves, 67% (or some high %) of 2nd M's end in D.

You need to figure out why you are so jealous and deal with it before you move on. I probably know 10 women (or more) that my H dated/lived with/slept with/whatever and I am even friends with some of them. I have no idea how many women he slept with or dated and I don't care because it happened before I even knew him, and that is how most people think. You need to understand why the things someone did before they met you bug you and even though you think it is just because you only dated one and they dated more, I don't think it is. That might make you feel like you missed out on something but it shouldn't cause a problem because you are upset that they didn't miss out on it.

We can't tell you what to do, however, it really appears that you are not ready for dating. Also, it's not really fair to date someone if your only intention is to 'catch up'.

Even though I try not to think about Xmas I still do. I can't even imagine any scenario that isn't seriously depressing in some way.

I know how you feel, I do that when things are bad, too. It really will get better though, even though it doesn't seem it right now.

OM2 to me isn't any different to me than OM1. Yes W wasn't upfront with me but my jealousy feeling towards any OM far far out ways anything else. To a point where it doesn't make sense to other people but to me it's massive!

I can understand jealousy feelings in this situation, however,
if others are noticing how jealous you are, and it appears extreme to them, it is another indication that it is something you need to address w/someone. Actually I'm not really sure jealous is what most people would feel;seems like it would be lots of anger and hurt. Not sure about that one..