Go for it. The anxiety will only increase over time. And then you’ll never do it and regret it. OR! Start throwing hints. Like really obvious hints. Bite him! Well- maybe not that obvious… but if you sit down and get it over with, especially if you’re sure there’s chemistry, he’s gay, and single, go for it! … I wrote a freakin script before she ruined my dramatics by trying to also tell me she liked me at the same time.