>>42092761. Be genuine. leave the uncle terry attitude at home
2. Do a workshop first so you can get an idea of what a shoot typically consists of if you're not sure.
3. Set a goal for the shoot. plan, plan, plan. location ideas, moodboards, lighting ideas, makeup ideas, etc etc
when it comes time to set one up:
professionals:
"hey, love your work! what are your photoshoot rates? I'm looking to shoot something like [this]" (helps if they've shot that style before)
or better yet, approach friends or friends of friends
"hey let's do a shoot"
[does shoot]
if that goes well, "hey let's do another shoot"
[does another shoot]
"hey, you feel like doing a shoot like [this]? looking to try somethign different"
This always worked well for me. If you're actually genuine and not some nervous neckbeard, you'll get them interested without too much of an issue.
Always helps if you have a girlfriend or a girl-friend to tag along and assist (give them a job. snacks, move lighting, hold a reflector, keep them on the lookout for clothing tags, flyaway hairs, etc).
GOOD makeup artists are wortwhile hiring as well, what you spend in makeup, will save you time editing