Q: Until about three weeks ago I was a 30-year-old man enjoying the benefits of being single, good looking and in a situation attractive to the opposite sex. Let’s just say I have had my fair share of hookups. I just started dating a woman whose company I really enjoy, to the point that I’d like to make things exclusive. But I have a question about the protocol of deleting the numbers of other girls in my phone. I don’t plan on looking up my past relationships while I’m with my girl, but what if things go south? I lose my database of hookups! I can’t exactly ask my new girl if she wants me to clean up my phone, and I’m admittedly not in a hurry to do it myself, unprompted. What do most people do in this situation? Am I a total jerk for even asking?


A: You’re not a jerk for asking, because this, my friend, is a universal issue. Everyone, every time they start an exclusive relationship, has the same moment: You’re sleeping over at your new companion’s place, or maybe they’re at yours. You just had an amazing night full of food, drinks and probing conversation. Maybe you just had sex — you know, that delicious, exploratory “new” sex — and you’re ready to fall asleep in each other’s arms, when your cell phone starts beep-beeping. Oops, you forgot to tell your regular booty call that you started seeing someone. That embarrassing moment is easy enough to explain, since, again, this is a universal thing your new partner will understand. And texting your former hookup the next day to let them know you’ll be out of service until further notice isn’t a problem. But now you’re faced with the dilemma of temptation. Do you clear out that number for good and, while you’re at it, any others that could lead to bad judgment in moments of weakness?

There’s no protocol for this predicament, because not everyone’s situation will be exactly the same. For instance, if you just cheated on your new girlfriend with a former hookup and she still took your sorry ass back, then you damn well better delete and tell the old girl to do the same. It’s just common sense. But what about those former friends-with-benefits or your go-to gal for erotic massage?

With the littlest bit of hesitation, I’m going to say that, no, you don’t necessarily have to delete your old hookups. It’s a beautiful thing to enter into a relationship being 100 percent positive that you’ll be together forever, but you also have to be realistic. We buy insurance for our homes and cars. Some of us sign prenuptial agreements, which are more or less marriage insurance. We do these things to protect our future interests in the event that things don’t go according to plan. Does a new relationship have to be any different?

Sure, if you’ve signed on to marrying someone or you’ve been in a long-term relationship for a couple of years, then you shouldn’t be squirreling away phone numbers as a contingency plan. (If you are, then you probably have a cocktail of commitment and abandonment issues.) But in the initial stages of a relationship, we tend to be overly optimistic about the outcome. There’s no need to rush ahead to the three-year stage when you’ve only been together for three weeks.

Don’t be stupid, though. Delete any and all naked photos of exes and ex-booty calls from your phone. You’ve got a new subject to photograph and admire during those long winter nights. If you do get called out on having too many numbers in your phone and find yourself having to get rid of some, only to break up with your girlfriend a month later, don’t worry too much. In the social-media age, the likelihood that you’ll lose contact with anyone for good is practically nil.