> but I carry myself confidently and I practice self love

But neither of these things actually convinces me you believe you are confident, or that you actually love yourself. It just means you know how to appear or behave as such.

> I wrestle with my feeling that I don’t deserve that type of love, that I’m past it somehow. That I’m already too jaded, bitter, or inferior (compared to other girls) to be fit for it.

And this only further proves it, you've resorted to relationships with older men as you don't have the confidence or self-love to feel that you deserve an unconditional relationship with someone your own age.

It's never too late to change that. People your own age will always be there and some will even be prepared to date you.

He needs to hear everything you've told us here. But it's possible it would turn into another argument, so if you feel that's highly likely, I think your best bet is couples therapy.

> but I also feel like I’m missing a core experience of my formative years—young puppy love without 1970s baggage.

I think you said it yourself, this is what I imagine you wish you knew.

I feel like this scenario (dated when you were young and still had growing up to do) is one of the few times I'd recommend giving it a try. So yeah, go for it if you feel you'd always regret it if you didn't try.

They can, but it's perhaps less likely.

Whether it's a club, movie theater, pottery class or bingo night, not everyone is there looking for a meaningful connection. Only a percentage of people are ready for that.

But go to a dating website and all of a sudden everyone is ready for a meaningful connection (if you sort out those looking for something casual).

If you are having a problem with this, you should change where you look for a more meaningful connection.

I think at 29 you are old enough to understand what you're doing. You are old enough to have had dating experience to the point that you aren't in danger of being taken advantage of, no more so than if you were dating someone closer to your age.

Because that's the problem with age gaps where one party is in their late teens or early twenties, even if the older party doesn't intend to, there will be a power imbalance by simple virtue of a massive gap in life experience, dating experience, and (perceived) maturity.

Until she recognizes she has a problem there isn't much you can do. Tell her you are there for her as a friend, but that you need to stop seeing evidence of her spending her money in the wrong places, no more talking about all the stuff she is buying while at the same time not being able to feed her child.

She will be upset, and she may cut off contact, but it's the hard truth she needs to hear.

The rule is: if you have to ask / if you think it would upset your s/o, it's probably cheating.

You came here to ask. So yeah, this is cheating. You need express permission from your wife for this to not be cheating. All you did was give each other permission, which isn't worth much.

It's probably some kind of roleplay dynamic and/or she plays a dominant role sexually speaking.

It's no different than "daddy" which seems to have been normalized.

Any way, just let them be.