Is it weird to play matchmaker for my ex? Hax readers give advice.

We asked readers to channel their inner Carolyn Hax and answer this question. Some of the best responses are below.

Dear Carolyn: I went out with someone for a few months then ended it. It was a genuinely lovely relationship but felt more like an amazing platonic bond than a romance and we drifted. She did not agree and was kind but very upset. It’s only been a week.

Here’s the thing: As we were writing to each other over the end, it occurred to me that she and my freshman roommate would be perfect for each other. I mean, like INSPIRED as a match. Soul mate level. They are the only two people I know whose brains work the way they do, and, in other important ways, they balance each other out.

So … do I do this? How long do I wait? How would I even go about it? I know this sounds like guilt-brain or something, but I’ve never had this instinct before. If I’m right, the rewards would justify the awkwardness.

Maybe Cupid: I applaud you for recognizing sooner than later that she’s not the one for you and breaking it off so you could both move on. My recommendation now is to actually let it end. No more writing back and forth, letting her disagree with you about it, letting her tell you how upset she is. Because yes, you are feeling guilty, and you’re looking to be let off the hook by handing her someone else. I understand the instinct, but let’s face it — it’s selfish. You’re looking to play hero and assuage your guilt by fixing her pain.

For argument’s sake, though, let’s say you’re still feeling this way several months from now. You can always approach your former roommate first and see if they’re even interested in an introduction before you stir the pot. And if they’re in fact a good friend, they can tell you whether they think you’re doing this out of guilt, some other self-centered reason, or because it’s indeed a truly “inspired” match.

Maybe Cupid: It sounds like you have a good idea, but you are the wrong messenger for it. Do you have mutual friends who know her and your old roommate who could make this suggestion? I think it would be a bad idea to suggest it to her directly. I wouldn’t be receptive to that from an ex.

Maybe Cupid: It’s only been a week, and the fact that she was hurt and upset means you err on the side of caution right now. If you’ve decided to try to be friends, set up a casual gathering or party and invite her, your freshman roommate, and some other singles/couples they know or could get along with. I would consider cluing in your old roommate (mention they have similar brains and you think they might hit it off) — if you guys are close enough and you can count on their discretion. Or don’t mention it to either one but see where it goes! Keep issuing group invitations and hope they find the time to chat and see what they think of each other. But you can only go so far.

Maybe Cupid: I find it endearing that you’re so inspired by the idea of this match. That being said, it’s hard to imagine your ex will appreciate hearing this from you at all.

Put yourself in her shoes: She’s dating someone she really connects with, and they end it abruptly because they’re not romantically attracted to her. I applaud you for your honesty and for not stringing her along, but that doesn’t mean it doesn’t hurt. You said, “She did not agree and was kind but very upset.” No matter how inspired the match with your old roommate, she is clearly not in a place to get set up — much less by the person who hurt her. The kindest thing you can do for her is leave her alone. If someday in the future you reconnect as friends, maybe you could revisit this. Otherwise, trust there are other people with brains that romantically complement your old roommate and your ex, without stepping in and inadvertently hurting someone more.

Every week, we ask readers to answer a question submitted to Carolyn Hax’s live chat or email. Read last week’s installment here. New questions are typically posted on Thursdays, with a Monday deadline for submissions. Responses are anonymous unless you choose to identify yourself and are edited for length and clarity.

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