Because I think it’s weird for all parties involved—my friends, the guy, me—I have a rule about not setting up anyone I’ve ever dated.

But a few weeks ago, a perfect storm of a situation compelled me to break that rule. My mom had become my roommate, nursing me back to health after neck surgery. She also played hostess to the constant stream of friends that came over to hang out and see how I was doing.

In anticipation of each guest, Mom got the 30-second info download, little reminders about how we knew the guest and any warnings about touchy subjects that were best avoided. Ninety-nine percent of the time, Mom behaved. (For all she did to help me recuperate, I’ve since forgiven that nagging one percent.)

Enter my friend from work: adorable, personable, smart, and warm. I knew her and Mom would hit it off, especially after I reminded her that my friend had also been engaged before and had really supported me when I became newly single. The thing about Mom is that she’ll be best friends with the person in front of her in line at the supermarket. Let her find out that you’re someone who looks out for me, and you are on her hamantashen list for life. (Read: she’ll send you homemade triangle-shaped cookies every year for the Jewish holiday of Purim.)

My friend told Mom and I about her boyfriend and how happy they are, but how much better it would be if her older sister would find someone. Here we go, I thought, Mom loves to play matchmaker. Quickly we had answers to all the important questions: the sister’s 34, lives on the Upper East Side, is an emergency room pediatric doctor, and wants to find a good, smart guy. While Mom would typically be first to jump in with suggestions, I immediately thought of someone, a guy who would not only be a great match for her, but also someone I would love to see find the right person. Without a second of hesitation, I blurted out, “How about 39?” (I’m using his age here to conceal his identity.) I guess sometimes we even surprise ourselves.


“39” is a guy I dated for a few months until he told me he couldn’t hang out with me unless I become his girlfriend. Despite breaking his heart, we have remained friends. We email, we text, we talk on the phone, and I am lucky to have him in my life. He’s a good guy with a good heart, and we get along swimmingly. Romantically, though, he just wasn’t for me.

When you have a person like this in your life, and other wonderful single friends surrounding you, is it selfish to keep them to yourself? Do your friends ever really want your sloppy seconds? Does someone who was once interested in you really want you to be the person to set them up with someone else? For those reasons and more, it’s always just seemed wrong to me. But in this situation, it just seemed right. Was I wrong to play matchmaker here?


Of course, I was wracked with guilt about it, because it seemed insensitive to nudge the guy who once wanted me to be his girlfriend into the arms of another girl. But we’re friends now; he’s a good person and has always been good to me. My intentions were simple: He’s single and looking, and he deserves to be happy. Moreover, I want him to be happy. So why not see if this girl fit the bill?


While I haven’t yet asked “39” about my friend’s sister, I’ve come to terms with my guilt. I think it was okay to break one of my rules. But tread carefully in like situations if you’re thinking of following my lead. You should be on the same page as your ex in terms of your feelings for each other, both past and present. There would be nothing worse than setting someone up who still holds a candle for you. I might also draw the line if it was someone you really loved. It seems a bit heartless, no matter how much time has passed, to pass off an old flame. But again, there are no hard and fast rules in dating, so play matchmaker at your own risk.

I also wouldn’t try this at home unless you’re really convinced that this set up could be a match. Try and connect people with like interests and personalities, not just because they’re both single. Put yourself in the situation first, too. Ask yourself, If I walked into a restaurant and saw the two of them sitting together, would it bother me? Be honest before you proceed. And even then, please do so with caution.


There’s this other guy who I went out on two dates with who was really great: tall and handsome, charming and smart, funny and well mannered. We got along perfectly but for whatever reason the two of us are better as friends. You know what though? He would be perfect for my best friend Jess.

I think I’m going to set them up.

Next Week: The unreturned phone call.