Is a 20+ Year Age Gap too High?

[Anonymous]

I am 28 years old and I've been on several dates with a 57 year old man

He is a senior manager at a large company & he used to work as a lobbyist. I find him really interesting and funny, but he is also extremely tall, handsome, and in shape too. I only met while working as a temp.

There are numerous red flags though. He has already been married twice before. I googled him online and found him linked to seven different women at various points in his life. And these are just the women he shared an address with at some point, so who knows if he dated even more.

I grew up in very sheltered environments and attended private Christian schools, so I don't have much relationship experience. I don't drink and I spend most of my time alone. So I kind of find the idea of an older, supportive partner attractive. I almost feel like he likes these parts of my personality though. I am a quiet person and most people find me boring to be around. I have terrible social skills and struggle to connect with people my own age

My own parents have a 23 year age gap. They are still married, but my mother never worked, my dad was out of the country most of the year, and my parents slept in separate bedrooms. My dad financially supports me and I live off a trust fund, so I technically never really have to work. It gets extremely boring and lonely doing nothing though. Especially since I have no real friends and I don't drink alcohol or go out with people my own age

I know a girl who is 26 and dating a guy 11 years older than her. But most people I know only have 2-3 year age gaps

[Anonymous]

I think if you go ahead with this given your background, he will run roughshod over you and (I mean this kindly) you don’t have the experience to get out of that situation. I would figure out what you want your future to look like — think about role models other than your parents — and decide if this man and your relationship dynamic fits into the future you want. Once you know what you want, do things to get there rather than passively waiting.

And go join a meetup for a hobby you enjoy or want to try. Not everything in every 20-something’s life revolves around alcohol. I don’t drink and didn’t in my 20s and am objectively boring and go to bed early and had no issue finding friends my own age, you just have to look in the right places.

[Anonymous]

Ew to me. Of course a 57 yo wants to date a woman in her 20's. But its seriously icky that he's old enough to be your dad (imo).

He doesnt sound like a catch either. Throw this one back.

[Anonymous]

If you are already supported by your parents, surely you can find better ways to pass time than be someone's medium term prostitute.

[Anonymous]

Everything about OP's post gives me the heebies.

[Anonymous]

Don't repeat your mother's mistakes.

[Anonymous]

If you don't even need to work, what exactly is the appeal of this 20+ older man?
I'm sure you can find many interesting, funny, in shape (while not exactly loaded) guys your age out there.

[Anonymous]

Seems extremely unfair to your father. You should give back the trust fund so he can give to your boyfriend's daughter.

[Anonymous]

Join Toastmasters. They are a supportive group and will help you gain confidence in public speaking and interacting with others.

[Anonymous]

You should be volunteering - at a dog shelter twice a week, and helping adults learn to read twice a week, etc. Why aren't you giving back to the community?

[Anonymous]

Works for Bill Belichick.

[Anonymous]

It's not clear if you work from your posts. If not, that would be a place to start. You could really use a life coach.

[Anonymous]

Guys, this is clearly a Troll.

[Anonymous]

Anonymous wrote:It's not clear if you work from your posts. If not, that would be a place to start. You could really use a life coach.

She said she doesn't work and doesn't ever need to.

[Anonymous]

I’m almost 50 guy and would love to date an almost 30 girl but whenever it happens I ick myself out and friendzone her. I can see girls having attraction to well maintained older men but the 20+ year (in your case almost 30yr) age gap is too huge. 10 ok. 15 maybe. But more than that and you are going to have major disconnects by the time you are in your late 30s/40s and this guy is step away from geriatric ward.