I never planned ahead thinking tonight is the night, which helped keep me from building up nervous energy for too long. I'd think tonight might be but let's see - Having a cocktail under your belt is also recommended haha but not 4 - i always said something when it became clear things could head towards sex, i.e. there was serious making out and a shirt or two came off. I realize this isn't always suggested but i never waited until they were reaching for a condom, just felt like it made it less of a big deal in that scenario than if i were to pull them aside over coffee or something. It's like ok, things are starting to heat up, let's have a sexual health convo. I always ask their testing history first then i would say ok, there's something that came up on a test for me i'd like to let you know about it - it's hsv2 and i've had it for x years. i didnt even know i had it and i've never given it to anyone - i typically let them then respond before i go into too much dialogue. My current bf was like ok, just let me know when we can't have sex - there was no need to go into stats with him or go through the nuances of my symptoms. You telling them is enough. It's their responsibility to then educate themselves. some people will have more questions. All of my bf's ended up doing research on their own which i found out later but even after dr. google, it didn't change their decision to be with me. hope that helps!