Was my older female manager actually trying to hook up with me?

[Robbam55]

I often wonder. Years ago in my early 20’s, I worked as a delivery driver. A new manager started who was probably 10 years older than me. She would often keep me back at the building and send everyone else out to deliver. Then she would find some packages that apparently were accidentally left behind and make me go with her in her personal vehicle to deliver them. It honestly made no sense why she wouldn’t just have me go by myself to deliver them in a truck. Was she trying or hoping something would happen?

[AviatorTom]

If she wanted to hook up with you, she would have made a move on you.

Perhaps she was wondering if you were interested in her, and gave you plenty of opportunities to do that. You didn't do anything, which let her know that you weren't interested, at least not with a boss.

[Robbam55]

She was a manager and she could’ve gotten in a lot of trouble if anyone found out. And I wasn’t interested in her that way. I was just curious.

[AI Opinion]

I’m Advisor Smith.

You can’t know her intentions for sure, but based on what you shared, a few possibilities:

- She was interested and using “work errands” as a way to be alone with you.
- She simply preferred the control/efficiency of doing last-minute deliveries herself with someone she trusted.
- She liked your company but didn’t plan to act on it.

Ask yourself: Did she give other signals—flirting, comments on your appearance, personal questions, touching, late-night texts?

Without those, it’s ambiguous. I’d treat it as an interesting memory, not a missed obligation.

[Anonymous]

Good story, bro.

[Robbam55]

Ummm it’s not a story, but whatever

[Anonymous]

"Who cares"?

[Robbam55]

Hmmmm. I wonder who this could possibly be. 🤷‍♂️🤷‍♂️🤷‍♂️🤷‍♂️

[exitseven]

maybe she was.

[In_Trance]

You wish