Dear Queenie,
I have a dilemma. I want to play matchmaker. My brother is a genuinely good man. Funny, kind, employed, emotionally intelligent, reasonably attractive (before he complains that I didn't say very attractive), and overall a solid catch. Unfortunately, his taste in women has occasionally been questionable. Recently, I gained a new co-worker. The more I get to know her, the more I think: This woman would get along with my brother. She is smart, grounded, pleasant to be around, and seems to share many of his values.” The problem is that I am nervous about introducing them. What if there is no chemistry? What if there is chemistry and then it ends badly? What if my co-worker thinks I am interfering in her personal life? And what if my brother embarrasses me? I keep fantasizing about engineering some sort of accidental encounter where they meet naturally and I can pretend I had nothing to do with it. Queenie, should I play Cupid or mind my business? —Sister with a Strategic Plan
Dear Sister with a Strategic Plan,
The fact that you are already plotting a "completely spontaneous" gathering tells me you have crossed from casual thought into active matchmaking. Welcome. The first thing to understand is that adults are not houseplants. You cannot place two people near each other, add water and sunlight, and expect romance to bloom. Sometimes the people who seem perfect on paper have all the chemistry of two tax forms. And sometimes the people you would never have paired end up planning a wedding. Now, regarding your concern: The safest approach is honesty disguised as low pressure. Not: "I have found your soulmate." But: "I know two people who might enjoy meeting." That removes expectation. The real danger is becoming emotionally invested in the outcome. Once that happens, every text message becomes a progress report and every awkward silence feels like a failed project. Remember: Your role is introduction. Not supervision. And please resist the urge to secretly arrange seating charts, carefully selected group outings, or suspiciously convenient invitations. People always know. Always. As for your concern about damaging relationships, that risk is lowest when both people are given a graceful exit. A simple introduction is a gift. An agenda is a burden. So yes, I think you can proceed. But do it openly, lightly, and with absolutely no expectation that they owe you a romantic outcome. And if they do end up together, prepare yourself. You will never hear the end of how they "met completely by chance." —Queenie
