How "bad" do you want to get him?
If it is really bad, hire a nice-looking, destitute girl and create and manage her LinkedIn and IG accounts. "Copy" his same interests (obviously, if he likes prostate exams, she can't copy that). Befriend the girls on his LinkedIn contacts first, then the guys who are friends with those girls. Work the six-degree-of-separation labyrinth. Remove a layer or two. Picometer your way in. Set the bait—most guys WILL bite!
True story on how NOT to do it: The feds had this gorgeous blonde Colombian fitness girl sit right next to me in first class on the flight from NYC to Japan. It was TOO obvious! They were too desperate. Also, prior to that, I had NEVER EVER had any girl sit next to me on ANY flight...unless I booked the tickets myself. Moreover, after that incident with the feds, I never ever had ANY girl sit next to me on any flight...of course, unless I booked us. The feds should have picometered their way in. First, figure out my workout routine and schedule. Have her be at the gym BEFORE I arrive to work on the same body part. Drink the same drink. Buy the same Kybun sneakers. Drive the same car but in a feminine color. Quick work in, request a spot (she had to go heavy), chit-chat, banter, and have her ride into the sunset! Rinse and repeat a few times more with the occasional out-of-sync plan.
Figure out my travel schedule. Find the events I go to. Have her sign up and be at the events before me. Picometer their way in. They are too impulsive! Too desperate! They have no impulse control. Their limbic system is damaged. Too many donuts.
This is the LONGGGGGGGG game.
An old guard and mentor of the ghost game once told me:
You can NEVER EVER arrive where the target is. The target has to arrive where you are!
You know what to do...like Nike says: Just do it!