Have you ever done something, or been asked to do something that at the time you didn't think anything of, but later you felt wrong or creepy about?

So basically, years ago, when I was 21, my girlfriends family (she's 19) asked me to escort their youngest daughter (age 17) to her prom. I'm confused, but it was my girlfriend doing the asking. I mean her family asked her to ask me. Now me being the loyal person, my only qualm was that it was somehow unfaithful to my girlfriend. So she assured me that she was okay with it, because "it's not like you're gonna be kissing or sleeping with her, and besides her boyfriend flaked" okay fine. So I took her. I danced with her once, took her to dinner after, and then home. Completely uneventful. Completely innocent. And of course I told the girlfriend all of this. And this was a nothing event. Looking back on it I don't feel like I did the right thing. Like I feel like I should have fought harder against doing it. Granted again no one got hurt, but I look at it as if I were a father, and there is no way in hell id ask or ask my daughter to ask, her boyfriend to escort her younger sister to prom. Even if nothing happens. Even if she's okay with it. It's not something I feel is the right thing to do.

What about you GAG? Oh and side note, the girl in this story who was my girlfriend, and I only lasted a year. It's a sad short story but when my grandfather died, she, when I came to her needing support or a shoulder to cry on, told me that it wasn't her problem.. So I found comfort in the arms of her best friend after I broke up with her.
Have you ever done something, or been asked to do something that at the time you didn't think anything of, but later you felt wrong or creepy about?
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