Reality Hour : Entertaining Coworkers

"Dear Sam, I'm a woman in my mid-50s who's been married and divorced twice.

I had my share of casual relationships and survived a few situationships along the way."

[laughs]

"At this point in my life, I'm not dating anybody and honestly, I'm good with that."

Yeah.

"I enjoy my peace, my independence, and going and doing my own thing.

My circle is pretty small.

I have a close male friend who's strictly platonic, a few female friends, and coworkers who are mostly women.

I don't really socialize with my colleagues outside of work, and I'm not looking to turn the workplace into a sh- a social club.

However, there are two younger men in their 30s who work outside my department, and we vibe pretty well.

We seem to have some common interests, especially activities I already enjoy doing on my own."

Mm-hmm.

"Every now and then, we text outside of work, and lately, things have gotten a little interesting.

One has mentioned that he'd like to actually join me in some of these activities, while the other has hinted that he'd be down for the same.

Now I'm wondering if I should entertain the idea of hanging out with either-

Oh, boy

... of them outside of work.

Let me be clear.

I'm not looking for romance, and I definitely don't want to give either one the wrong impression, although I admit one of them is attractive.

I'm grown enough to recognize a good-looking man without automatically wanting to make him my man.

At the same time, I've lived life...

I've lived enough life to know that mixing business with pleasure can be messy real quick.

I value my peace, my reputation, and my professional boundaries, and I'm not trying to create an awkward situation at work over something that might not even be that deep.

Am I overthinking this, or is there a way to enjoy someone's company without sending mixed signals? Should I kick it with these guys after work, keep things strictly professional, or leave well enough alone?"