scorecardresearch Skip to main content

5 things Dinner with Cupid’s matchmaker has learned about love

What a woman who sets up blind dates every week knows about the mysteries of compatibility.

Gracia Lam

A matchmaker can’t win.

Put two daters together who have everything in common — down to, say, a mutual interest in the ukulele — and the night can still peter out into the “friend zone.” But pick your matches by the old saw that “opposites attract” (Exhibit A: my own marriage of 13 years) and what’s the takeaway refrain? What on earth was Cupid thinking?

Despite matching Boston-area singles week in and week out in this magazine’s Dinner With Cupid column, I find the ingredients that factor into love — chemistry, attraction, and those absent from an application form, like sibling order and pheromones — are still often cloaked in mystery. Yet whether you’re gay or straight, a man or a woman, I’ve gleaned a few observations about the search for old-fashioned romance in the time of Tinder.


1) Timing is everything: Twentysomethings believe they have all the time in the world. As comedian Aziz Ansari has observed, the generation can’t commit to a restaurant, much less a soul mate, lest a better option come along. This infuriates older readers, who know that spending three companionable hours with someone and not wanting to stab them in the eye with a dinner fork . . . well, it ain’t nothing. But don’t tell that to a recent coed who rates her date an A but is jetting off to grad school. If the timing’s not right, perhaps it wasn’t meant to be.

2) Yet don’t get hung up on time: To all the terrific, accomplished thirtysomething (and forty- and fifty- and even sixtysomething) women seeking men whose applications are languishing in our pile: we apologize. Men of a certain age are hard to come by. Are they all taken? Out swiping right? Hard to say, but remember, women can date younger people, too.

3) Traditional gender norms die hard: Women seem far more likely to be looking for love — in a given week, females outnumber male applicants by a sizeable margin (note to men: we dare you!). Yet some romantic stereotypes persist: Although we reimburse our couples for the cost of their meal, a guy invariably still picks up the initial check. And women — even those of decidedly average height — can be quite vocal about their height requirements in a mate, typically, they say, because they can’t bear to give up their 3-inch wedges (who says they have to?). Interestingly, men almost never voice preferences for weight or body type.


4) Embrace the mystery: Our daters often marvel how the hours flew by. Why? Most likely because our singles can’t conduct a full background check via social media ahead of time. Many say one of Cupid’s great allures — and stresses — is the rarity of going into a date truly blind, gradually peeling back the layers of the stranger across the table sharing the creme brulee. Before exhaustively Googling that attractive someone, consider the pleasures of a slow reveal.

5) Declare yourself: Looking for love in a magazine column isn’t for the fainthearted — and probably attracts more than its share of extroverts. But one thing is for sure: Those who do apply aren’t ashamed to declare to the world they are looking for love. And perhaps that’s all it really takes. How often do we comb through the database and pluck out the perfect applicant, only to find she’s already found love on her own, thank you very much. Disappointing? Yes. But not really surprising.


So go forth, young lovers (of all ages) — be bold, be brave, break some rules, keep the mystery alive, and seek the passion you deserve. We promise to keep trying if you will.

Melissa Schorr is a Globe Magazine contributing editor and the author of the new YA novel “Identity Crisis.” Send comments to and apply to go on a date at