How Long Should I Wait?

I’ve been romantically involved with this guy for 8 months. I’m technically his boss. I just turned 30, he’s about to turn 23. Our personalities really meet in the middle.

We’ve been friends since he began working with me. I was in a relationship for almost 4 years, and he was in a serious relationship himself. I took him to a concert at the beginning of the year since my bf couldn’t go, and then we started talking everyday. Long story short, we were both unhappy in our relationships and opened up about it, started liking each other, you know the drill.

Eventually, when Covid hit the fan I got scared to quarantine with my boyfriend and didn’t want to not see this guy, so my feelings came out. His were mutual. We ended up breaking up with our S.O.’s shortly after.

He was very into me, said he couldn’t wait to officially be with me, and I said I wanted to take a little time going slow and getting to know him on a deeper and romantic level. He was fine with that. We hung out 1-2x per week and kept it casual.

A few months later, he became very distant and hesitant to be around me or show affection. His grandmother passed, and his grief over his lost relationship and the “trauma” from how abusive she was kicked in. He said he didn’t want to stop hanging out, but needed some space to clear his head and make sure he was okay. I did that for him, but he still texted me some with some mixed signals. Later that month he said he wasn’t there with me like he was when we first started, and he was just depressed and it was bad timing. When I told him to just let me know when he wanted to continue this, he texted me that night and then asked me to hang out the next day. We did, things went great.

Fast forward a couple of months, things are really great. We are planning a weekend cabin trip and it came up that he had a bad experience on a trip with his ex. I asked if he trusted me, he said he didn’t know but he liked me. That turned into a talk about our relationship. He told me he didn’t want anything serious, he was still messed up over his last relationship. I asked what we were doing then, and he said “we’re just chillin, I’m not trying to put pressure on us.” This hurt me and as we continued to talk, we ended with us being “committed” to one another, not seeing anyone else, and working towards an official relationship. He told me all the boxes are checked… we’re just not boyfriend/girlfriend.

Since then, it’s felt very much like a relationship, but we still only hang out 1-2 times a week. We went on the cabin trip and it was great, really relaxing, nothing got too heavy or serious. I’ve met his brother (in context) and his parents (out of context). He texts me good morning every day. We call each other babe, love, baby, etc. and have referred to one another as “yours” and “mine”. He’s even said “I’m becoming much less hesitant and more comfortable in our relationship, and I’m starting to really differentiate you and my ex as two completely different people. Thank you for showing me what a healthy relationship looks like,” and told me how much he liked me. He’s there for me and he’s very supportive. We are physically intimate and are open about how great it feels with one another. We miscommunicated the other day when I was upset and said “I can’t do this,” but meant something else, and he thought it was about us and got very scared and taken back. That told me, among other things, he really does care. Feels like he’s my boyfriend… but he’s not. 

So we’re in November, we’ve been talking every day since January. Things are going well and it feels like a relationship, but I’m still not his girlfriend. If I was, he would have asked. I don’t want to keep bringing up a “define the relationship” talk because I don’t want to pressure him or push him away. But I want to be with him officially, and even though he says he’s committed, is he really though? I know he’s not a bad person, he’s not going to hook up with anyone else but I know deep down I want true commitment and to be his girlfriend. I’m worried he’s concerned about our age gap, I was actually a rebound (he said I wasn’t but), or if he just likes having his cake and eating it too.

I don’t know how long I should wait around for him to ask me to be his girlfriend. I really don’t want to pressure him and I want him to have the time he needs, but it’s been a while now and there wouldn’t be much of a difference other than some more hang time I think. I want to be honest, but I don’t want to scare him away. I want to understand and be patient, but it’s starting to hurt me. I don’t want to just walk away, I really, really like him, and I know he likes me too.