Please be kind with me! I always mean well and have good intentions. I’m just in a position where I’ve started a new career role (overwhelming in and of itself), while also trying to see what unfolds when it comes to relationships (I’m at an age where there’s more pressure). Any help/advice is appreciated!

My guy friend (Bob) and I got a bit too friendly at a nightclub. It wasn’t like anything drastic happened, however we did hug several times flirtatiously which he mostly initiated. I might’ve initiated the very first one but it was pretty mutual. I didn’t know how to deflect his multiple hugs especially in front of our peers where we usually have to be so PC and professional. Somehow, we started chatting after leaving the club, and I’m not sure how the topic came up but it was likely when he stated that I looked uncomfortable. I mentioned I just wasn’t expecting us to get so physically close in a short period of time, at a nightclub nonetheless, even if it was hugs. I explained I tend to be more conservative with intimacy and we also just started our professional roles.

Our chat got so awkward, and I found that he has manipulative tendencies. He has constantly given mixed signals, pretended not to remember basic details about me that we’ve talked about admitting that he likes to mess with people, got defensive stating he doesn’t want to be friends as this will be weird, he wants to tell his best friend about all of this, drank a lot and said he drove so it seemed he wanted an excuse to hang out. The punchline was when he said he doesn’t think we should date and then asked if he hurt my feelings as it apparently looked like I was going to cry. I was confused because nothing had even started between us, and I felt like he was being really presumptuous or wanted to upper hand. He wavered back and forth, said he liked being friends with me and the group we’ve formed with his best friend collectively, apologized a few times for potentially leading me on. After all of this, he also told me he had been wanting to kiss me, clearly wanting to drag out the one on one time so late at night. Ultimately, we agreed there’s mutual attraction but not enough or proper that we should act on it. We agreed one of us has to be the stronger one and I walked away first.

The big problem now is his best friend. I caught some type of feelings for him right before all of this happened and was actually hoping to see him. I made sure that Bob knows how much I value my friendship with his friend, with himself, and us as a group. He said he won’t tell him details like the hugs but he does want to bring up the awkward gray area moment. My stomach is unsettled because I believe Bob planned this all along, as soon as I had a great deep talk with his friend with him in earshot earlier that same day. I think he got jealous and may ruin my connection with his friend. He even said he thought I’d make a nice couple with his friend. I asked if we should just all 3 sit together after a meeting we’re attending tomorrow, and he deflected it. I get that he’d want to have real talk with his friend, and I told him point blank I’m not trying to meddle, but I now feel like I really need to do something from my side.

Should I tell his friend when I see him in person today (Bob won’t be there)? If so, what do I even say and I should text Bob a heads-up right? Or give Bob more time to tell his friend since he’s busy this weekend? Stepping back, is there anything to even tell Bob’s friend? Because of the hugs or mainly that it became a gray area between friendship and romance? How can I deflect hugs without making guys feel rejected, especially when others are watching and we need to be very professional in this group? Is Bob someone I should stay away from and what could I have done better? Any other advice or thoughts are welcome. Thank you!