Advice - when to bring up topic that could lead to a disagreement

bunny💙

First time posting here, my boyfriend and I have been together for 6 years. Currently have been long distance from September-now, but I’m on the semester system for school. We spent about 2.5-3 weeks together between Sept-Oct, i then came home for thanksgiving break and a month for xmas break. We’ll be seeing each other for the first time since January this coming week.

He’s going to school for one year on the other side of the country (currently we’re both on the west coast which is why we’re able to visit frequently). I wanted to talk to him about some stuff I’m worried/nervous about, my boyfriend is very sweet and doesn’t always pickup on social cues. As a result of being so nice, but literally not being able to tell the difference between people being nice or flirting with him, he’s had some female friends that have gotten too close and once he’s aware he’s set boundaries but it’s typically after the fact. I’m worried about what his social life will be like, and if he’ll be able to maintain those boundaries without me around to warn him or point out certain behaviors, since he really is oblivious. I wouldn’t believe he was oblivious if it wasn’t for the fact that he didn’t even know when I was flirting with him before we got together either lol.

I don’t want to have a disagreement when he’s only staying for a week. He gets defensive and upset if he feels I’m accusing him or upset at him, but I think we can have a decent and productive conversation if it’s conducted the right way and i don’t wanna do it over text. Would you recommend I talk to him now, in February when he’s visiting for a week, or wait till next month when he’ll be here with me for about two weeks?