Treading Lightly

(If you don't wanna read my whole post, I'm a son in his 30's who has a crush on his mom in her 50's.)

With out getting into the long winded details, I always had a very (and some would say weirdly) affectionate relationship with my mom. For reasons I could guess at but not say for sure, she has always been my number one fantasy, with no close second. Probably everyone here knows that it's normal for very young boys to have crushes on their mom, and that's how far back this goes, but for me those feelings just never went away.

As I began turning into a man, there were a small handful of instances between us, nothing too big, but that retrospectively make me feel like it's actually plausible she feels the same way. I'm actually starting to think she probably does at least a little.

I'm my mom's only child, dad has other kids (probably part of why my mom and I are so close.) I'm now in my 30's, parents in their 50's - and they recently separated. My parents' separation is brutal on everyone, and I never have or would wish it. But I'd be lying if I said it doesn't have me wondering if there's some way I can test the waters to see if my mom would reciprocate a sexual advance.

And that's how I ended up here. Rn I'm just trying to figure things out and sort my thoughts. Making a move isn't something I'm considering any time soon. I'd only consider it if I felt there was a way I could test the waters gradually enough that I can turn back before I ended up hurting my dad even worse. As much as I want her, I want my dad to be okay even more. The only reason I'm even considering it is my bc my mom and I are friends as much as family, and I actually think if I tried something on a night where we'd been drinking wine, even if she isn't interested, she'd just call me an idiot and not tell anyone about it.

Sorry this still ended up being long winded,
Alex

Like where your head is at. I was in a similar situation once upon a time and didn’t act, it’s one of my biggest regrets. That being said sounds like you understand the gravity of your decision and aren’t rushing any decisions, good on you.

Good morning, Careful, and welcome to Kindred Spirits. I’ve upgraded your account.

There are ways that you could test the waters with your mom, and they’ve been discussed at length here. No big secret, just go slowly and carefully and always leave yourself, and your mom, with a way to gracefully back off if things get awkward. We can talk about your situation in particular in the members-only groups if you’d like.

Peace,
UN

Welcome aboard!

Love the story. Thanks for sharing it. You are right to weigh the considerations of other family members. I would have said this would be almost impossible if your parents are still married and living together. That they are separated helps. Seems you hit on the toughest issue: the fact you have a closeness with your dad. It is worth considering what would happen if anyone found out you and your mom decided to go down this path. If you are sure you want to do this, or if you want to know if she has similar thoughts, then at some point you're just gonna have to ask outright in some way. I do advise steering things to the stage where asking openly seems the right thing in the right moment. It would be worse for you to always wonder and never know if she thinks the same way - meaning you stay in this state of limbo forever and you get to a point it's too late. Mind you, it will be the hardest conversation you will ever have; the hardest question you will ever ask. But you will know definitively one way or the other - which is what you would need. Hoping for you that you get what it is you want!!!

Regardless of what else you decide to do; you said the separation has been hard on everyone, so the first order of business would be just to be there for your mother. She'll need a lot of support while she heals.
I think most of us would agree, the most important thing right now isn't what you want but what she needs. Whether or not you ever approach her about a physical relationship, being her support now would strengthen your family relationship.
Another consideration that you didn't bring up is whether you're in another relationship. If so, that would be someone else you need to consider.