I have had a crush on a gentleman for quite some time. If he ever asks me out and we become a couple, when should I tell him about my STD (Herpes II)? And, then ... HOW do I tell him? This has kept me single and alone for a long time because I just don't know how to do this.
Well, don't lead with the STD. There are things to tell a fella on your first date (you're a vegetarian, you have a teenage son, you've always wanted to see Spain) and then there are things to tell him before he's got your undies in his teeth (I have an incurable STD that gives me contagious genital sores).
Look, everyone has weird, scary crap that a partner is going to discover when the clothes come off and the guardrails come down: A battle with alcoholism, piercings gone awry, a tendency to hurl cutlery during PMS. Couples cope with stuff; they work around it. If acknowledging your disease is just another way of stripping naked before a potential partner, then make it part of the seduction: "Can I be honest with you? I've been thinking about how amazing it would be to make love with you. So I need to tell you that I have Herpes II. Do you know much about it?"
Tell him that one in five U.S. women between 14 and 49 have it, that it's less likely to be passed from women to men than vice versa, and that it's a condition you've learned (or are learning) to manage. Then hand the baton back to him, asking — with a smile — what makes him a challenge in the sack. Be disarmingly casual but painstakingly honest; condoms can reduce the spread of STDs, but ain't no prophylactic can staunch the spread of lies.
In the last several months I have had the dubious distinction of having not one, but two different women tell me that I have "that sexy-ugly thing going on." Is that an insult or a compliment? I'm confused.
You have that insult-compliment thing going on. The term "sexy-ugly" comes from the 2001 movie Kissing Jessica Stein, and refers to a guy who's delicious without being conventionally good looking. The movie cites James Woods, Lyle Lovett, and Harvey Keitel as examples; I'd add Keith Richards, Alan Rickman, and Tommy Lee Jones. So you're in excellent company, and these women are trying to tell you, "I'm not supposed to be attracted to you, but I am." Still, I'd take the compliment and run. Anyone who would tell a person that he's any kind of ugly wants to be perceived as pop-culturally literate more than she wants to be perceived as polite or kind. And that, my sexy friend, is just ugly-ugly.
For what it's worth, Lady Gaga has a song called "Sexy Ugly." Perhaps you'll find its riveting-stupid lyrics enlightening: "You sex pot. You sex pot. You are a sex pot. You are a sex pot. You, sex and pot. Yeah." If not, just go with what I said before.