Okay, today was kind of interesting after work...
So I'm friends with one of my co-workers, but strictly thus far in a work setting. We'll call her "A." Now I'm very reserved at work and keep it as professional as possible, but she and I do joke around now and then, and we've both had terrible pasts. I don't push her about it, I don't want to pry. But I have a feeling that it is similar to my own. About a month ago, I gave her my number so that we could go out to eat (platonically) and discuss whatever was on our mind, but she never got back to me. It's worth noting that we only work together maybe once per week.
Anyway, today was such a day, and it just so happened that we both ended the day at the same time. I made a joke that we should go to the bar after work (she knows I don't drink, but has invited me to the bar before to hangout, so it was almost like I was joking with her). I then refined it to just going out for bar food, and she agreed. So we go to the bar and she tells me that she's got a work secret to tell me. So she tells me that one of our managers (we'll call him "B") ran into her while she was out drinking a few weeks ago, bought her a ton of drinks, exchanged numbers with her, and has been asking her out over text. He's like 20 years her elder, and she says that he's just not her type. So she told him no, supplying him with the "don't mix work and play" excuse. Furthermore, she said that work has been kind of awkward and a bit standoffish between the two of them. Now I like B a lot, he and I get alone fine. But he does seem kind of like a lonely, aging guy who would cling onto a girl really fast and make things awkward for everyone.
So we actually had a great meal. She and I can talk very easily with one another, and against our appetiser of why she and B are not compatible, I basically started talking to her about a lot of her interests - books, traveling, philosophy, religion, etc. Again, we're co-workers and we are mature enough to keep it civil, but we both definitely noticed that it was "pleasant" to have a deep, mentally-stimulating conversation with another human being, when neither us expected such out of our day. We probably talked for 90 minutes, we talked a lot about concepts like guilt, shame, regret, attachment, nostalgia, and so on. Again, I never pressed her on her past and she doesn't know the specifics of mine, but she said I helped her a ton, gave her a lot to think about, and that she "never has conversations like this with anyone and it was really nice." I enjoyed it too, it's rare that I can relax and enjoy myself around people, but she's cool. We both probably feel like if we didn't work together, we could have some fun (she was being very flirtatious in ways toward me), but again, we're beyond capable of interacting at this level without anything being awkward and just appreciating what we have and not craving more.
But ya, if my boss B found out that I took her to the bar and bought her dinner, and/or that she thinks that redleader is a very fascinating person, nothing good will come of this. The younger new employee comes along and takes his crush, the one who won't date him because he works with her, out on what sounds (to him) like a date. I work with this guy like 10-15 hours a week ALONE IN A ROOM, and he has the ability to fire me. It was unfortunate that I didn't know that he was pursuing her until after she and I already decided on dinner, but it is what it is. I don't want to necessarily say to her "A, let's not tell B that we're socialising at all," as this would look weak of me, and perhaps like I am breaking the unspoken bond A and I have and speaking about romantic connotations that shouldn't even be brought up.
And I don't want to abandon my growing friendship with A, as she is cool and she and I could help each other out I think. But I also don't exactly want B to know that A and I hang out outside of work, as it will just make it awkward between he and I.