Dear Tell All: I grew up across the street from a family of four, which includes a girl five years younger than I am. Our families were cordial but not terribly close. We’d have the occasional meal at each other’s houses and support one another in various ways. I mowed their lawn; they’d sometimes come to see me play baseball. A couple times my family went to see the young daughter — I’ll call her Kayla — in children’s theater productions.
I never interacted much with Kayla, given the difference in our ages. She seemed like a sweet girl, and that’s as much as I ever thought about her. But I temporarily moved home after graduating from college and doing an internship in Chicago, and was stunned when I saw her across the street. She was heading off to school with a couple other girls from our neighborhood, and she looked beautiful. I couldn’t believe the change from the skinny, immature kid I remembered.
Not long after that, I had a conversation with her in front of her house as I walked our dog. She surprised me again with her poise, intelligence and sense of humor. I felt weirdly shy and self-conscious talking to her, even though I’m so much older. But I felt a connection, and I’m pretty sure she felt it too.
So here’s my question: Would it be weird to ask her out? Would the age difference — my 23 to her 18 — make me a creep? Would it be worth the funny looks I’d get from our nosy neighbors?
Romeo
Dear Romeo: You said “here’s my question” and then asked three of them. I’ll take them one by one.
Would it be weird to ask her out? You clearly feel weird about it, so that pretty much means it’s weird. But that alone shouldn’t stop you from asking Kayla out.
Would the age difference—my 23 to her 18—make me a creep? No. You’re both young adults, so where’s the problem? You’re attracted to her poise, intelligence and sense of humor, which are rare qualities in a person of any age.
Would it be worth the funny looks I’d get from our nosy neighbors? If there really is a connection between you two, then yes, it would be worth it. Why pass up the possibility of true romance based on what the neighbors think? I predict their funny looks will turn to beaming approval if you and Kayla become an item.
Romeos who don’t take chances rarely find their Juliets.
Do you have a question about life or love in Madison?
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