Today: Apr 21, 2024

Ask Annie! Dippin’ in the Family Jeans

Dear Annie, 

I’ve been talking to this girl in my class and we’ve met a few times for drinks and dinner at the bar. We never made it seem like official dates when we did go out; it was always just casual. But one night, I asked her out for a real date, I got her flowers and picked her up at her house. I’m starting to really like this girl and can see it growing into a strong relationship, but once I rang the doorbell that’s when the trouble started!

Before I go any further, let me just say I went to a house party about two weeks ago and met a cute girl there. We were talking and one thing led to another and we hooked up.  So when I rang the doorbell, guess who answers…the girl from the party! The smile fell off my face and instead a look of confusion overtook me. 

It wasn’t ‘till my date was walking down the stairs when she said, “Sorry Dan for the wait, this is my sister. Ready to go?” I was awestruck. What do I do if I hooked up with her sister before her? Her sister kept looking at me, winking, shaking her head with that expression of, “I won’t say anything.” But can I really trust her? Should I say something first, so she hears the story from me instead of her sister?


Dippin’ in the Family Jeans

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Dear Dippin’ in the Family Jeans,

Personally coming from a family of sisters, they talk. So don’t trust her sister not to say anything. Tell her what happened, it’s best to be honest right up front. Especially if you get in too deep. Then if she does find out from her sister later on, maybe it’ll be better if you told her first. 

Follow your heart and take it slow with her, also her reaction to the whole hooking up with her sister probably won’t be good, so prepare for an argument and make sure you explain yourself. That way you don’t look weak or lustful trying to defend your actions. 

Also, it might get awkward if the relationship blossoms and the day comes when you two do the deed; especially if it isn’t as good as it was with her sister. It’s a very sticky situation you got yourself into honey, so you got to tell her. Be honest. As always be safe; no glove, no love. 



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