Friends- age differences

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This is a good point. Standard business etiquette is that when someone interviews you but you do not get the job, the interviewer does not contact you again unless he is seriously looking to fill another position and in that case the discussion should be business-only on the level of a second interview - no “you’re so pretty” stuff because that’s generally verboten in an interview.
Yeah, so this man basically crossed the line two times already for certain.

OP, it would be good to listen to your instincts.
 
Do any of you have a friend who’s much older than you, or a lot younger? There’s this old man who’s an attorney that has taken a liking in me. He would compliment me and tell me I was beautiful, and that he thought highly of me. I thought that was very nice of him to say, however, now it seems a bit weird. He emails me, and he wanted to take me to dinner one night. I don’t think he means anything by it …just strictly a friendship. I think he just enjoys my company from when we met. But, he is 80 years old and is married. Anyways, recently he suggested that he take me to supper on Monday and for me to come by his office around 6:30-7pm. The first time he asked me to dinner I asked if he would invite a lady friend of his, who he had told me about before. I didn’t end up going though. I could ask him to tell her to invite her, but I don’t know if I even feel comfortable going out to dinner with an 80 year old man who i don’t know too well. I guess I am not used to having friends this much older than me. plus, I feel it’s weird that he wants to take me to dinner when he has a wife. Maybe lunch but dinner just seems weird to me, even though I don’t think he means anything by it but friendship. i didn’t respond to the email. Do any of you think I am overreacting or is this actually weird to anyone else?
Yeah, I’ve had younger or older friends. Those are sometimes challenging situations when despite the equal footing the other person still exhibits the same patterns as your parents or your children.

Just like you, I somehow find it difficult to think a married man in his eighties would mean something by inviting a younger lady friend to supper. Rather, he may be living according to the etiquette and sentiment of his own time (some decades ago) and exercising some privileges granted by age or status (such as exemption from suspicions that would otherwise arise), on which account it’s possible he sees no impropriety in the whole thing.

Just like with other married men, you can always mention how you’d like to meet his wife and watch his reaction (though there may be more than one reason why a man would feel awkward about that, e.g. if he has a bit of a jealous or otherwise eccentric wife, or a strong introvert).
Sadly, this is the crrepiest part of the post. You do not befriend people you meet at a job interview. But business boundaries. Unless he gave you the job, and you have daily contact, it is wrong to be friends.
Perhaps if you judged the candidate negatively. Not necessarily if there was simply someone more experienced or with higher credentials willing to work for the same salary.
This man being married and telling you you’re beautiful and wanting you to go to dinner without his wife present is red flag number 1. The fact that he has another “lady friend” to include in this is red flag number 2. Doesn’t matter if the man is 18 or 88.

A man acting as a mentor or business career advisor will invite you without making compliments that would be considered inappropriate or even sexually harassing in a workplace environment.
Large age differences sometimes lead to large cultural differences. As a rule, older men are more liberal with compliments toward women, more chivalrous in general and also speak more directly, with less fear about political correctness or exaggerated accusations of harassment (especially brave folks who’ve been to a war or two and looked armed guys in the eye while shooting or stabbing at 'em).
 
Large age differences sometimes lead to large cultural differences. As a rule, older men are more liberal with compliments toward women, more chivalrous in general and also speak more directly, with less fear about political correctness or exaggerated accusations of harassment (especially brave folks who’ve been to a war or two and looked armed guys in the eye while shooting or stabbing at 'em).
I’m not young myself and I have known many lawyers. Many of them were polite and courtly older men such as you describe. I do not get all uptight whenever an older work colleague compliments me on a new dress. My mother before me worked in offices with a lot of older, powerful men in military and government for many years and likewise she appreciated when they had nice manners and taught me to do the same.

There is a big difference between politeness to a colleague or someone you meet, and an older man speaking to a younger woman whom he interviewed for a job but did not hire, telling her she’s pretty and asking her to go out to dinner without his wife. This is not a “cultural difference”, it is crossing the boundary of appropriate behavior and sending up red flags. The OP realized this and that is why she felt uncomfortable.
 
I’m not young myself and I have known many lawyers. Many of them were polite and courtly older men such as you describe. I do not get all uptight whenever an older work colleague compliments me on a new dress. My mother before me worked in offices with a lot of older, powerful men in military and government for many years and likewise she appreciated when they had nice manners and taught me to do the same.

There is a big difference between politeness to a colleague or someone you meet, and an older man speaking to a younger woman whom he interviewed for a job but did not hire, telling her she’s pretty and asking her to go out to dinner without his wife. This is not a “cultural difference”, it is crossing the boundary of appropriate behavior and sending up red flags. The OP realized this and that is why she felt uncomfortable.
Great insights! I agree.
 
I’m not young myself and I have known many lawyers. Many of them were polite and courtly older men such as you describe. I do not get all uptight whenever an older work colleague compliments me on a new dress. My mother before me worked in offices with a lot of older, powerful men in military and government for many years and likewise she appreciated when they had nice manners and taught me to do the same.

There is a big difference between politeness to a colleague or someone you meet, and an older man speaking to a younger woman whom he interviewed for a job but did not hire, telling her she’s pretty and asking her to go out to dinner without his wife. This is not a “cultural difference”, it is crossing the boundary of appropriate behavior and sending up red flags. The OP realized this and that is why she felt uncomfortable.
I’m not entirely convinced. I think the huge age difference may be another factor setting the mind at ease about any perceived impropriety. I can also see why the OP felt uncomfortable, and I certainly would have felt uncomfortable myself in her shoes. What I’m not convinced about is some of the conclusions and reasons for them that I see in this thread, along with the whole trope of having interviewed but not hired her etc. (Unless this is a cultural difference — I’m from Europe, familiar with American culture but not inside out.)
 
I wouldn’t feel comfortable going out to dinner alone with a man unless he was family. Maybe ask if you can bring a friend?
 
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