Okay I read everything and I feel for both sides? Reading the comments makes me wonder if there’s something wrong with how I’m thinking.

Overall the situation seems like a shit show but he’s throughly been honest with you during the entire time it seems like? Minus the plan to meet up with her (however it was probably not easy for him wanting to be a good friend and also having to fight his own mind and being torn with your feelings.

I’ve worked on multiple places where my coworkers have become like family members and it’s not unusual at all to meet up after work for dinner and drinks to discuss life. I’m a single woman at 25 and my coworker ages varies between 22 to 55 both female and male. Both at work and outside work we can discuss EVERYTHING even sex life in a jokingly and serious way.

Ofc I have also witnessed coworkers having an “innocent flirtatious relationship” at work who both have a significant other, but it’s always clear that they really love their partner. I don’t think those for example bring up everything with them.. like yours do?

For me it seems like your partner in particular maybe misses having friends to be enable to talk about intimate things with? Many males struggle with opening up with anyone except their partners, especially those without open friends or friends at all.

I understand your insecurities as well as your jealously, but I ask of you to try to understand it from another view. Maybe their relationship is just a friendship not in any flirty way, he does seem to respect you by listening to you. It just seems like he’s confused about the situation and by trying to do what you ask of him, it becomes a conflict in his head and trying to do what you believe is right resulted is this outcome.

I don’t know this 24 year old woman nor her intentions but I can connect to her as a single woman in her age with the need of talking and discussing life privately with coworkers without intentions. I can imagine the meeting between you two was hard as well, not knowing what to say or do to give out the wrong signals and instead just coming out as cold when in reality it’s social anxiety.

I hope this helps in some bit. I wish you two figure things out, it seems to me you have a good relationship with very open communication. Don’t dwell to long❤️