A letter with a 'plot twist'.

mrsconn23

Dear Prudence,

So, say you were in the middle of a long dry spell. You’ve dated, but none of the men really interested you. Then, there is this guy that is several years older than you who is unattached. At work, neither of you report to the other, but you see each other, and are members of the same non-work groups—book club, gym, game-night groups, that kinda thing. He’s almost your dad’s age, you’re a few years older than his oldest kid. He’s been divorced for a few years, you’ve never really been attached or engaged. If he asked you out, would you freak out? Would you end the friendship? You’ve been out together many times for drinks or dinner, both alone and with friends, he’s very current culturally, and very passionate about things that you care about. I’m the guy in this scenario, you’re the younger woman. The woman in question is 43, I’m 69.

–(Not) a Cradle Robber

short+sassy

26 years is not a "few years", smh.

LW, would you be interested in a 95-year-old woman who shares all your interests and is "culturally current"?  No?  Then that's probably pretty similar to how this woman feels about you.

MyNameIsNot

I wouldn't date someone I worked with full stop. If it wasn't for work, I'd say ask her out and see what happens, but work makes everything more complicated. It's a big age difference, but 43 is old enough to see an older person for what they are.

Maybe wait and ask her out at your retirement party?

banana468

It really depends.  

STARMOON44

I would find it creepy and end the friendship. Im
40. If I had a 67 year old friend I hung out with from time to time and then when he judged me most likely to be desperate for a man he asked me out, I’d feel like the whole friendship was a lie. 

levioosa

Yeah this is a one way ticket to a sexual harassment suit at work involving HR. Leave her alone. 

mrsconn23

I'm turning 42 soon and my dad is 68.  Just...no.  

Also, is she really spending one on one time with you OR are you both just the last ones to leave the table on occasion at the end of a group dinner? 

CharmedPam

I don’t think this can end well.  Partly due to work but the age difference which doesnt matter now, but will down the road

charlotte989875

I actually don’t mind the age gap here if both parties are on board. Work is the bigger issue. How closely do you work together? Are you in the same building or potentially work on similar projects. Could you work ever impact here or Vice versa? If yes then the answer is don’t pursue it. 

I work at a huge company. Theoretically, in my previous role  (since this obviously isn’t my situation) I could meet someone in a completely different division and never interact with them in a professional capacity. My current role is enterprise wide so that’s not the case now, but when I did division specific work there were definitely lines of business I never would interact with. 

short+sassy

mrsconn23 said:

I'm turning 42 soon and my dad is 68.  Just...no.  

Also, is she really spending one on one time with you OR are you both just the last ones to leave the table on occasion at the end of a group dinner? 

I don't necessarily have an issue with an age gap if both people are interested in each other.

But in his entire letter, he never mentioned that she flirts with him and appears interested romantically.  If that was the case, I'd think he would have included it.

Because while May-December romances may happen.  Most people, from both sides of the age gap, are not interested in them.  There will always be extra challenges, like being in different life stages.

Also, the average life expectancy for men in the US is about 73 years old and this guy is only a few years away from that.

I also had a lot of bad experiences when I was in my 20s.  Granted, no one I knew well and hung out with socially.  But so many middle-aged guys hitting on me, both online and in person.  It was creepy and gross, so that has become my default setting when I hear about a man who is interested in a woman 20+ years younger than him.