My partner and I moved to Winston last summer. We have kids so we don't know much about the nightlife except that there is one gay bar in Winston called CO2. I've read mixed reviews online. Last fall, Winston had its first pride celebration in 15 years. We were out of town but heard it was well-attended (which for here means about 5000 people) and fun. Equality Winston holds gay bingo nights to raise money for pride and other causes. I see "our people" everywhere here, most notably at Whole Foods.
We've not had any issues in Winston with feeling unsafe. But we are a female couple and I know we sometimes have it easier than male couples. Still I think you'll feel plenty comfortable in downtown Winston. I don't have personal experience with High Point but I've heard that's it's more conservative.
Here are some links for you: equalitywinstonsalem.org, goqnotes.com
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