Dear Uncle Gary,
I’ve been dating someone wonderful for about six months. We laugh a lot, the chemistry’s great, and I’m genuinely crazy about her. Lately, I’ve been wanting to go deeper, share more of myself, and learn more about her. But whenever I ask about her family or her past, she either changes the subject or says she doesn’t want to talk about it.
At first, I chalked it up to privacy or timing, but it’s starting to feel... off. I even tried looking her up online. Nothing came up. No social footprint, no breadcrumbs.
I don’t want to be pushy, but I also don’t want to ignore my gut. Should I press for answers, or give her more time and space?
Signed, Curious but Cautious
Dear Curious but Cautious,
You’re not wrong to feel the tension between patience and curiosity. Six months in, it’s natural to want more than just good vibes, you want depth, history, context. You’re building something real, and real things need roots.
Now, her reluctance could mean a few things. Maybe she’s been hurt. Maybe her past is complicated, or painful, or just not something she’s ready to share. That’s valid. But so is your instinct. When someone consistently dodges basic questions about their life, it’s not just mysterious, it’s isolating. You’re trying to build intimacy, and she’s keeping the scaffolding hidden.
Here’s the move: don’t interrogate, but don’t tiptoe either. Tell her what you told me. That you care about her, that you’re invested, and that you’re starting to feel a little shut out. Frame it not as a demand for answers, but as a need for connection. If she’s not ready to open up, fine, but she should be able to say why, and reassure you that it’s not a red flag, just a closed chapter.
And if she can’t do that? If the mystery stays sealed and the silence gets louder? Then you’re not being cautious, you’re being wise.
Keep your heart open, but don’t ignore the part of you that’s asking for clarity. That part’s got good instincts.
