Since you’re asking this question, I take it you’ve already jumped the first hurdle, which is staying attracted to your walking STD boyfriend. Good for you! Second: of course sexual history should matter. Any part of a person’s history matters—whether he was convicted of manslaughter or used to have a compulsion to lick telephone poles, for instance—because it makes a person whom he is today.

The key is to figure out what life lessons he’s learned from his promiscuous history. Did he use it to learn about his (probable) insecurity issue and grow into an amazingly secure, sensitive lover who’s tuned in to a woman’s needs? Or did he only learn how to successfully usher one girl out the back door when the next is coming up the front walk? The only way you can get past his past is to spend time getting to know if he’s past his past. Also: you might want to consider not putting out whenever he wants. If he still sticks with you, some life lessons might have stuck with him.

The Resident hosts a NYC TV and Internet talk show, which airs online at www.theresident.net. She has one of the All-Time Most Subscribed Director Channels on YouTube, has millions of online views, and was voted one of the Best Internet Personalities of 2007 by Yahoo! Video.