Flirty boss vs mentor close in age

[Anonymous]

Men, what line do you draw with subordinates relatively close in age? Both single, you are a parent. She is not. Both are well established in your careers for your ages.

Is a HH lasting 6 hours normal (only the two of you)? Mix of personal and biz talk.

Not looking for more than a boss/mentee relationship...but at times it felt date-ish....maybe I have just been so isolated during Covid.

[Anonymous]

6 hours is a long date, not a happy hour.

[Anonymous]

6 hrs is date territory. The boss needs to be careful when doing 1:1 socialization with those working below him/her, but especially if they are opposite sex.

[Anonymous]

6 hours is well past a happy hour more like looking for a happy night.

[Anonymous]

That is definitely a date.

Be careful.

[Anonymous]

Over the years I had many women report to me when I was both single and married and I would only do a happy hour with a group and never lingered afterward. You are simply putting yourself at risk, innocent or not, and it wasn’t worth it. Just being a mentor has risk as others might see favoritism as a trade for sex. I did mentor women but I was always very careful. But I did marry a coworker/peer so I certainly wasn’t a saint in the office.

[Anonymous]

PP are you the subordinate or boss? The subordinate may feel pressured to stay at HH with the boss, and therein lies the underpinning of a Me Too moment...

[Anonymous]

I am the subordinate. Admittedly, attracted and definitely did not feel pressured to stay. If I wasn’t his report and met him randomly, I would be interested.

Most of my male mentors/bosses have been way older and most outings (unless coffee or lunch during the day) have always been in groups.

Couldn’t tell if I was reading wayyyy too much into it or if we were maybe pushing an inappropriate boundary. Certainly seems like the optics to others are what I was thinking regardless of what he was thinking (as much as I hate to admit, kind of interested what was running through his head).

[Anonymous]

He’s clearly interested.

[Anonymous]

Anonymous wrote:I am the subordinate. Admittedly, attracted and definitely did not feel pressured to stay. If I wasn’t his report and met him randomly, I would be interested.

Most of my male mentors/bosses have been way older and most outings (unless coffee or lunch during the day) have always been in groups.

Couldn’t tell if I was reading wayyyy too much into it or if we were maybe pushing an inappropriate boundary. Certainly seems like the optics to others are what I was thinking regardless of what he was thinking (as much as I hate to admit, kind of interested what was running through his head).

You clearly have an interest in this guy and maybe he has an interest in you and your options are very limited. You either shut it down or ask to be reassigned so you can pursue it.

[Anonymous]

You are both single so it is morally fine, but could be a professional problem. If you want to pursue/be pursued I would look into different employment

[Anonymous]

6 hours is a long date and certainly not happy hour. He likes you beyond mentoring

[Anonymous]

6 hours at the same bar? I can't imagine doing that with anyone, even if I was clearly on a date with someone I was very interested in! You are either hungover today or the staff was angry at you for nursing your drinks and wasting room for new customers who were spending money.

[Anonymous]

Anonymous wrote:6 hours at the same bar? I can't imagine doing that with anyone, even if I was clearly on a date with someone I was very interested in! You are either hungover today or the staff was angry at you for nursing your drinks and wasting room for new customers who were spending money.

Yes, same bar. Closed it down. We were spending money and tipped generously.

It also wasn’t full and we were not hogging a table.

[Anonymous]

Anonymous wrote:Men, what line do you draw with subordinates relatively close in age? Both single, you are a parent. She is not. Both are well established in your careers for your ages.

Is a HH lasting 6 hours normal (only the two of you)? Mix of personal and biz talk.

Not looking for more than a boss/mentee relationship...but at times it felt date-ish....maybe I have just been so isolated during Covid.

I think this is fine. I’m 10 years older than my boss and we recently drove from our office in VA to Georgetown for lunch than wandered around before having a drink at bar. We’re both married and I don’t think of it as a date.