Going Against My Better Judgement

[TheRugbyValkyrie]

He and I have been distant friends for around 3 years. I'm very much older and it started as a professional relationship.
He's funny, kind and very sweet. He has always made me feel hood.
I'm a single parent with 4 children. Mental health issues and deliberately single for the last 17 years.
Saturday. I taped his shoulder. We joked around. I looked out for him more than usual.
I decided to go out. We were inseperable. I finally confessed to feeling more than friendship and immediately felt like an idiot. He spent the next hour persuading me that its ok and its mutual. Came home, fooled around a bit.
Long Sunday morning in bed, lots of kissing and me finding reasons that this is a really bad idea.
I worked yesterday. He wanted to know about my day.
He is coming to spend the day either me today.
Tell me that this really is as bad an idea that I know it is. I'm too old. I have a child older than him.
Talk me down.

Well an enjoyable casual relationship/fling is not a terrible idea, but if you catch feelings, it is .... Because significantly younger men rarely stick around for ltrs.

I know age is supposed to just be a number, but it isn't really, is it? I'm guessing he's at least 20 years younger which is a really big age gap, and any relationship with him has the potential to really upset your children.

If you're the type of person who could just enjoy a discreet fling and let him go when it's run its course, I'd say 'go for it', but I get the impression you're not?

Mental health issues and deliberately single for the last 17 years

Hmm, maybe best to avoid getting involved in a relationship that is very likely to end after a fling. He's not thinking about your mh or welfare. He'll return to his young, single, responsibility free, presumably child free life with a milf fling as a nice memory and knotch on his bed post. You already have enough on your plate without risking catching feelings and being v hurt when it ends.

*notch

Nope. Enjoy it. Might be a one week thing, a mont tthing or more. We need enjoy these things when they fall in our laps.
How old ia he?

Depends on your life philosophy op. I am leading an 'enjoy the day' life, so I'd take the relationship and enjoy it as long as it lasted. Others look in to the future more.

I'd agree with this in many situations but your clearly vulnerable. With 17 years of MH issues and low self esteem/insecurities doesn't sound like a fling (or even relationship) is what you need.

If you could go into it eyes open I would say go for it, but sounds like you already have feelings never mind a few months down the line.

Or is he claiming to have feelings for you?

I will try to address some points made.
My mental health issues started when I was a teenager. I got a new psychiatrist at the beginning of the year and I don't think I've felt so a peace with myself.
I made the choice to stay single 17 years ago.
Regarding my feelings. It's complicated. I know I'm not made for a ltr. I've tried it. Can't do it.
He doesn't claim "feelings," but is open to see what happens.
My children pretend I have no life and discretion has always been a big deal for me.

He is 27. Old enough to know better and young enough to make me think twice.
Having said that, discretion has always been a big deal for me, regardless of how close I've become to my players.
First time I've contemplated something like this, I guess that's why I'm questioning myself.

I've always been open about my MH. My old boss always said, "You may be a nutter, but you're our nutter."
That does mean that although I'm friendly & caring, I let very few people in.