For me, it would be a few days to a week or so chatting online? It's mainly to filter out the guys who are reckless, on drugs, or tend to ghost people? I am looking to make bi (or gay) friends more than sex right now. Don't get me wrong, still wanting the pleasure of sex, just prefer to have an ongoing acquaintance? And preferably know someone well enough that if they had an STI, they'd hopefully alert me? I know that's a big ask in this day and age. All I sadly know is that many bi guys are fickle when it comes to making friendships or meeting in person if sex isn't involved? There is going to be an epidemic of lonely, friendless men, suffering from their own behavior! Recently had one publicly out bi married guy, making plans to meet for lunch next week, block me! Because after 4 weeks, I said I planned to use a prostate massager toy, trying for a p spot orgasm. Asked if he had ever experienced one? First time I brought up anything sexual. "I don’t like the unsolicited details about your sex life". We were talking on a gay sex app for shit's sake! All he had to do was just say, hey, not comfortable with that kinda talk yet, & I would've zipped it?! But nope, treated hours of conversation over 4 weeks as disposable! And the dude was a male nurse, acted squeamish like I just sat next to him on a bus and said this? I would never try to initiate with a guy in person, unless in a gay bar or club? I can't imagine the confidence, balls, and skill that LowHangers and KDaddy23 have breaching the topic in regular spaces with guys that are not obviously flaming gay or waving a pride flag around like they just took a hill in battle?! Lol!
Breaching the topic in regular spaces is... one of those "what does the situation feel like" kind of things. You're sitting with the guy, talking, maybe not paying a lot of attention to what he's saying but how he says it, his body language, other mannerisms. Looking him in the eye; noticing if he's sitting/standing closer or keeping his distance. There are so many things that I know, instinctively, that'll tell me whether or not I can breach the topic with him and right along with my own "plan" should he beat me to the punch and breach the topic. How does he react to a tiny bit of flirting? Is he tossing a little flirting at me? Instinct will tell me if he's down with the dick and I can't point to any one thing that "tells" me this. God knows how long and how many times I've approached a guy and have either guessed right about him or, gulp, I was wrong and now I'm apologizing; I've screwed up enough times to have learned how not to screw up... kind of. It's always a crap shoot and I've also learned that if you don't play, you can't win. My prize will be my mouth around his dick while his is around mine, first timer or not.
This has been my personal situation with men myself. A good hour talking while having a few drinks and if the "vibe" goes in the right way then how about we get naked and pleasure each other because we are both wanting that to take place so let us get busy doing so. If getting naked is not an option at the time or an available atmosphere, then why not suck each other off in either one of our vehicles? Blowjobs are so easily provided in just about any setting and when done correctly sends him and yourself home more than satisfied for the night.