I’m confident one of my new female co-workers would be an excellent match with my bro. They have tons of common interests and their personalities are very closely matched. I’ve mentioned him when talking to her, and she has been receptive (though never showed any direct signs of interest). My brother would be all for a set-up. What is the best way I can go about setting them up? Should I ask her if I could give her number to him (and then get him to text her)—I feel like that would take some pressure off her. —Question via Reddit, edited for length
Morgan Olsen
In a relationship | 28 | @morgancolsen | RedEye Eat & Drink, Lifestyles editor
Some people love being set up and others don’t. I have a hunch that your co-worker is being nice and indulging your need to play matchmaker, but it doesn’t really sound like she’s champing at the bit to go out with your brother. Plus, you’re putting your professional relationship with her on the line if something goes awry. I’m not saying your brother is a bad dude, but perhaps it’s not the best idea to mix and match your co-workers and relatives. If I were you, I’d play it safe and abort the mission unless she goes out of her way to ask about your brother.
Fred
Single | 34 | @fredonair | Host of “Fred and Angi in the Morning” on 103.5 KISS-FM
A thoughtful setup is a beautiful thing, but you need to keep your hands clean considering you are dealing with two central parts of your everyday life: your work and your family. If you feel that strongly about a potential match, the only thing to do here is provide each person with contact information for the other (with their permission), and allow the rest to happen organically. You laid the bait, but after making the connection, you have to allow the rest to happen as it may. The last thing you want is for this thing to implode and one or both party is mad at you for forcing the matter. So set it and forget it. If your idea fails, maybe you’ll get “good guy” points for trying. If it’s a huge success, take all of the credit in your speech at their wedding.
Courtney Jacquin
In a relationship | 24 | @courtneyjacquin | Writer and editor
I think the easiest way to go about this would be to set up a casual social event with both your brother and co-worker. Maybe you have an after-work happy hour with some co-workers, and you invite your brother to join. Casually introduce the two, and see if it’s a hit. You might not know everything going on in the woman’s life, so giving her the phone number of your brother might put her in an awkward position if she’s not really looking for anything right now. If it’s meant to be, it will be.
