Read the leaflet that comes with the tablets to see if it's safe.

Yes. That is not a sleeping pill, it is an anti-histamine that has a side effect in that it tends to make some people sleepy.

I would not worry.

50 mg of dyphenhydramine hydrochloride is two Benadryl. That's used as both an antihistamine, and a sleep aid. It's very mild. With the wine, the effect would be somewhat more powerful, but not dangerous.

I would wait 4 hours before taking the tablet. Not the 2 or 3.

Yea it's fine just 50 mg isn't much when I was in my teen years I'd take like 200-300 mg of that stuff at once because it can get you high iv also smoked weed on it and taken it with dextromorphon so just that and a little wine certainly won't hurt you

According to some of the answers on here you need to be cautious because if you take sleeping pills regularly they may already be in your blood stream.

https://www.quora.com/How-long-after-drinking-can-...