But how does one in the OP's situation engage a wingman?
I was afraid someone would ask that. Perhaps the most difficult task, if he doesn't already have a candidate among his existing friends.
I found mine online. Before the spread of the internet in 1994, using a local dial-up bulletin board system (BBS), I had already befriended this gay guy prior to realizing I was gay myself some months later (a long story in itself, as most of mine are
So when I came out I knew who to ask, and he was kind enough to help. He knew all the gay spots in Seattle, knew many guys in the community, would accompany me to places, make it all easy. He also wrote articles about HIV/AIDS in the Seattle Gay News (SGN), was a fierce proponent of safe sex and hammered those practices into me, which were all new to me.
I was such a novice I know that without him I would have made ignorant mistakes, and might not be HIV negative today. So that his mentoring extended beyond helping me to learn the social ways of the gay community, and to overcome my shyness, but also to keep me healthy in a risky new environment.
Among the many things the Army taught me was to locate & rely upon experts when you're engaging in something where you have little knowledge & experience. And even before that, to recognize and acknowledge that you DO need assistance, something many men are typically reluctant to do. It's related to the "won't stop to ask driving directions" syndrome to which males seem so prone.
And so I had no hesitation to ask this guy for help. And later as his contacts helped me to network in the gay community, I also asked THOSE guys for help, a constantly spreading web of human resources I could draw upon. And once again I had as my model the Army, where we were reassigned frequently, and had to fit-in and adjust to a new command & community rapidly in order to perform our jobs, to "hit the ground running" as much as possible.
The Army would even formally assign a "sponsor" to you, especially in overseas assignments, to get you up to speed and assimilated quickly in a new place for maximum effectiveness. So you can see why this line of thought would be natural to me, now being applied to joining the gay community.
If the OP would like to try this approach, but sees challenges in getting started, we can continue to help him here with suggestions to make that happen.