Dear Urban Diplomat: Am I betraying my best friend by accepting a free Drake ticket?

Dear Urban Diplomat, Since high school, my best friend and I have talked about seeing Drake live. When he discovered how much tickets were selling for this year, he flipped out and immediately took to social media to rage about the odious pricing. Meanwhile, my very-connected cousin landed two tickets for free and invited me. Even though I’m not a superfan, I really want to go! What should I say to my friend? —Guilty Pleasure, Little Portugal

If your friend is old enough to attend a concert, then he should be mature enough to swallow his envy. Tell him exactly what happened: you were given the chance to see Drake for nothing, and though it will hurt to go without him, you really want to. It’s not his place to kibosh fun with your family. If he’s indeed your best friend, he’ll be happy for you—and he may even revel in the fun vicariously.

Dear Urban Diplomat, I’m a single woman about to turn 40. I froze my eggs when I was 36 and promised myself that I would have a baby on my own if I was still without a life partner by this age. The other day, a dear friend, a man who is gay and married, offered to donate his sperm—no strings attached—as a birthday gift. It was an incredibly generous gesture, and I was so overwhelmed in the moment that I thanked him and accepted right away. Now I have regrets. He’s got great genes, but I want to pick my baby’s father from a neutral pool of swimmers at the sperm bank. How do I reject him without hurting his feelings? —Daddy Issues, Sherwood Park

This is probably the biggest decision of your life, so careful consideration is key, and wavering is to be expected. Tell your friend that, while you truly, deeply appreciate his kindness, you want to avoid conflicts that could arise if you were to follow through. You may want to involve him in your future child’s life, and shared DNA would complicate that relationship in ways you can’t imagine. Short answer: it’s better for all three of you if he’s not genetically invested.

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Dear Urban Diplomat, I’ve been a freelance designer for decades. Recently, one of my clients—who treated me like trash—was fired from her agency. She’s since reached out asking if my other clients are hiring. No surprise: her tone was a lot friendlier than it had been the entire time we did business. I am sympathetic, but I don’t want to recommend a bad egg to one of my good customers. Nor do I want to be a perpetual doormat. Please help. —Role Reversal, St. Lawrence

You shouldn’t risk your reputation or your relationships with your clients on this unpleasant opportunist. You have two choices: explain that you’re not comfortable recommending her and outline your exact reasons, or chicken out and just say that you’re not aware of any openings but will keep her in mind—then ghost. I’d understand if you opted for the latter.

Dear Urban Diplomat, My boyfriend and I have been together since last fall. We’re totally into each other, and our feelings are getting even stronger now that summer has arrived: patios, bike rides, Pedestrian Sundays and so on. But there’s one summer activity I just can’t dive into: public pooling. I get the jitters when I think of floating Band-Aids, hair-clogged drains and diaper mishaps. The problem is that he grew up by the Christie Pits pool and considers it sacred. I don’t want him to think I’m a snob, but I’m out of excuses. What’s the play? —Not Some Flotsam, Liberty Village

Don’t worry—plenty of us avoid swimming with camp kids, hungover teenagers and octogenarians doing aquafit. There are some things we do as couples and some things we don’t, and that’s perfectly okay. Mention that you’ll still go with him but will stick to people-watching poolside. He has enjoyed the Pits his entire life, and he should continue to do so. Being honest and giving him the freedom to keep swimming will place your relationship on solid ground.

Send your questions to the Urban Diplomat at urbandiplomat@torontolife.com.