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Dear Annie: My granddaughter has a boyfriend who keeps cheating on her -- three times now, and those are only the times I know about. Each time, she takes him back, swearing he’s changed. I’m old enough to know how that story ends.
She’s smart and kind, and I hate watching her with someone who doesn’t treat her the way she deserves. I’ve bitten my tongue up until now -- it’s her life, after all, and she’s entitled to her own decisions -- but I don’t have the heart to sit quietly through this when it inevitably happens again. How do I get her to see what I see before she wastes any more years on him? -- Watching From the Sidelines
Dear Watching: You can share your opinion, but you can’t control someone else’s actions -- and with a granddaughter, you especially can’t order her heart around. Tell her once, plainly and without repeating it every visit: You see a pattern, and you worry about her. Then let her draw her own conclusions on her own timeline.
You’re better off saving your energy for being there for her when she’s ready to see it herself.
Dear Annie: My husband built our family hardware store from a single rented storefront 35 years ago, and he’s finally ready to retire. Our son, “Jesse,” has worked the counter and the books alongside him for the last eight years, and he’s good at it. Customers ask for him by name. The plan was always for him to take over.
But recently I’m starting to wonder if that’s the plan because it’s what Jesse wants, or if that’s just the plan because, well, we’ve always assumed that was the plan. He’s never said he doesn’t want it. He’s also never said he does. I would love nothing more than to see the store carry our name for another generation. But I love my son more than I love the store, and I don’t want him spending his life running it just because none of us could bring ourselves to ask the real question. How do I find out what he actually wants, without it feeling like I’m guilt-tripping him? -- Hoping It Stays in the Family
Dear Hoping: Ask him directly, and make it safe for him to say no. Tell him plainly that “I don’t want it” is an acceptable answer. Eight years of showing up doesn’t prove love of the work; it might just prove love of you. Give him room to tell the difference.
“Out of Bounds: Estrangement, Boundaries and the Search for Forgiveness” is out now! Annie Lane’s third anthology is for anyone who has lived with anger, estrangement or the deep ache of being wronged -- because forgiveness isn’t for them. It’s for you. Visit http://www.creatorspublishing.com for more information. Follow Annie Lane on Instagram at @dearannieofficial. Send your questions for Annie Lane to dearannie@creators.com. COPYRIGHT 2026 CREATORS.COM