Dear Wendy: “When’s The Best Time To Discuss STDs?”

After getting dumped by my boyfriend of five years (and some time to get over that), I’ve recently re-entered the dating world. So far it’s a lot like I remember it to be; however, the only difference is that this time I’m not a virgin, and neither are most of the people I’ve been out with. And while I’m not quite ready to leap into bed with anyone, I’m becoming increasingly confused about the appropriate time to broach the subject of getting tested for STDs. Is there a way to bring up the topic without being offensive? I feel like I’m being a bit of a prude here, but after working for a college health center for a few years, and seeing the damage that STDs can do, I’m just not interested in putting my health at risk, even in the name of love. — Cleared for Takeoff

There really isn’t a right answer to this question; it’s entirely dependent on you and the pace of your dates and what feels comfortable. Certainly, before you become very intimate, you want to have that conversation. If you’re someone who might sleep with someone on the first date — and I’m guessing you aren’t — you’ll need to broach the subject pretty early. If you’re inviting him back to your place or vice-versa, it can be as easy as saying, “You’ve been tested, right?” Or: “When were you last tested?” Obviously, if you ask a question like that in the cab over to your date’s place, there’s an implication you’re ready to have sex, so don’t ask if that’s not the case. If you prefer taking your time in a relationship before you jump into bed, you can take your time broaching the topic of STDs, too. If things are going well after a few dates, you might casually suggest — not in the heat of passion — that you both get tested soon. You can use that opportunity to talk about your time working at a college health center. It’s not the sexiest of conversations, but there’s really no reason to fear it or be embarrassed. A lot of guys will totally respect you watching out for you (and their) health.

I divorced at the age of 28 with a 2-year-old son, and have been single for most of the last 25 years. I am now 52 years old, and dating a very sweet man who is patient, kind and genuinely caring. We’ve dated for just over two months. He’s been divorced about a year after 25 years of marriage. His name is Chris and Chris still refers to this daughters’ mother as “my wife, I mean ex-wife.” That doesn’t really bother me since he was married for 25 years. I have suggested he call her by her name, which I just found out is Debbie, so hopefully that will help.

The real problem is that there has been no fooling around … no hand holding, no passionate kissing — just a peck on the lips … after six dates. I don’t know what to think or how to approach this. I’m ready to fool around — some heavy making-out would be a good place to start but he isn’t giving me the vibe. I don’t want him to think I NEED to get laid but I enjoy getting laid. My concern is that he may not enjoy it as much as I do? For sure, he’s not had as much experience as I have but I prefer not to bring up the ‘number of partners we’ve had’ topic. I just don’t know how to approach this intimacy thing without sounding desperate or slutty or make him feel pressured. He is a bit overweight and that could be a concern for him. I’m confident he likes me because he continues to ask me out and we have so many interests in common.

How do you suggest I proceed? My ex-husband was gay which I discovered AFTER I married him and I want to be sure this guy is straight and enjoys intimacy. — Ready To Rumble

You wouldn’t have mentioned Chris referring to his ex-wife as “my wife” if you didn’t think it related to the issue at hand, and you’re definitely on to something. If Chris hasn’t yet fully made the disconnect between his life with wife and his life as a single man, it’s probably very hard for him to think about putting the moves on another woman. That certainly doesn’t mean he doesn’t want to or that he hasn’t thought about it, but between having what’s probably a bit of an identity crisis and feeling utterly inexperienced in the dating world, his confidence is shot. Why don’t you make things easy on him and make the first move? There’s nothing slutty or desperate about a grown woman taking the lead after six dates with the same guy. If he responds to your advances, great! Hopefully, that gives him the ego-boost he needs to make the first move next time. If he doesn’t respond to your advances or he seems awkward, take the opportunity to check in with him and find out what he’s feeling. After six dates, it would not be out of line to ask what the deal is with the lack of intimacy. Just be respectful and mature about it. You might be the first woman other than his wife whom he’s been this close to in nearly thirty years. That’s a big step for someone.

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