There aren’t many trickier questions to navigate than the Hokusai wave of “How many people have you slept with?” It can be a perfect storm of insecurity and jealousy. One of you may be left feeling inadequate and inexperienced while the other is left feeling a little slutty, or worse, regretful. People make all kinds of gaffes when exploring the unchartered waters of this question.
But fear not, readers. I’ll be your Christopher Columbus. (Because I know I’m not technically the first one to offer this advice, but, damn it, I will get credit!) With my help you’ll be sweeter on your baby than John Smith was when he laid eyes on that epic babe Pocahontas. (I only know the Disney version of this story.) Okay, enough with the seafaring metaphors and onto the sex. Foremost, you need to self evaluate. Are you going to get jealous? Storm out of the room? Are you going to hold their number against them? No explorer ever made it without a plan. I mostly don’t ask because I am a jealous person. I’d find out who those other guys (or girls) were and slowly build cases against them like I was Jack McCoy. Not only did I dwell over all these new Eskimo siblings but I’d also keep them inside me as evidence against the kingpin: the person I was dating. Nothing can break down the perfect little rainbow of your relationship faster than jealousy. Even if it’s a full-on double rainbow.
Of course, if you’d rather not know, there’s a chance your lover might. Be ready to tell them why you don’t think it’s a good idea. Say you don’t want to talk about the past because it can ruin the present. Say you don’t think it’s a good idea because if your numbers are vastly different then one of you is going to be left with a scarlet letter and the other with an albatross. I’ve been branded with the scarlet letter and I’ve watched the albatross weigh down lovely people into thinking there is a deficiency in their sexual ability. It sucks. If you don’t think one of you can handle it, maneuver your vessel far, far away.
But let’s say you think you want to talk about it. Jealousy is totally 2011 and you’re all about the here and the now. Great. Be prepared to answer your question first. In fact, you should really aim to answer first. If you’re the one who wants to know you have to be able to show a little courage. Be Buzz Aldrin, not John Glen. Buzz Aldrin made the moon his bitch by stepping all over it. Your loved one is going to be a little nervous when you bring up this question so show some courage and say “I have slept with XYZ number of people.”
After you have asked the other person and you have both shared your answers the real problems can arise. There are basically three positions at this point. This is how you should handle each one:
1. You are the sexperienced one. Congrats on all that sweet lovin’ you have accumulated over the years. You need to be a little sensitive toward the other person because your lover may feel a little insecure. Is it less than a five person difference? Okay, no big deal. Is it a 20 person difference? That’s going to be fine, too. But remember that as much as that other person is going to try and not make this discrepancy a big deal (and it might not be) your number is the bigger number and if we know anything about Americans it’s that bigger is ALWAYS better, right? No, but seriously, don’t be a dick about it. Maybe reassure your lover or something. Angle your number appropriately. Say something like “Well, baby, I wouldn’t know how to do INSERT SEX THING HERE to you so well without all those other scrubs. (Make sure you call all the others scrubs.) Don’t shame yourself but let them know that they are more than just another number. And try and laugh about it. Laughing always helps.
2. You are the in(sex)perienced one. Okay, cool. Don’t panic or anything. The important thing is to stay present. Don’t let your mind wander to all those other people. It’s not a home-run derby. In fact, let’s keep in theme and say it’s about how far you hit the ball, not how many times you hit it. 1-500ft home-run is worth 100 ground outs to first. There’s a good chance a portion of their sexual encounters were brief. The secret about one and done sex that no one ever tells you is this: Yes, sometimes it does feel good to just get laid. But nine out of 10 times the best sex you’re going to have is with someone who you care about. You develop a groove. You know they like it with you more than those other people because they keep coming back for it. Trust me. Some of their escapades have been lack luster. Plus wouldn’t you rather be “the best I ever had” if it meant you outsexed 25 guys? It’s not a competition. But damn it’s great to be the winner. Also, you should never shame your partner. Just as there are perfectly acceptable reasons for not having sex, there are a ton of reasons for having a lot of it. If you want to play Rick Perry’s hit board game “Moral Authority” than you shouldn’t have started this conversation.
3. You have the same (or a comparable) number. AMAZING! You lucked out. You both are at two, 20 or 200. Sure you may have gotten there different ways. One of you may have been the turtle — adding two or three to the bed post every year for the past 10 and the other the hare — wilding out freshmen year in what many describe as a “sexplosion.” But hell, you found yourselves at the same place. I don’t even have to write more about this because this is the ideal. If you screw up the conversation at this point — your relationship already had issues.
The important thing to remember that you couldn’t be the person you are today and they couldn’t be the person they were if either of you had different experiences. They might like that you’ve had a bit of practice. They might like your new car smell. Whatever the case, they care about you. Otherwise, why would they put themselves through this awkward endeavor? It’s not an evaluation. Lean back, relax and remind them why they like spending 16 hours straight in bed with you. Soon they’ll forget about those other two, 20 or 200 and you’ll be the most important number in their lives: #1. (Cue Nelly’s “#1” as you ride off into the sunset.) 
