[bravosierra]

I met a woman recently through my job and I’m unsure of how, or if I should pursue a relationship with her.

I am a rideshare driver (Uber, Lyft, etc) and picked up a woman for a 30 minute drive. Along the way, we had a great conversation and had a lot in common. I tend to key in on details and there were a lot of things she said that really just clicked for me. The company I was driving for has a policy against asking for dates or making advances on drivers or riders. I’ve never had a passenger that I had any desire to see again, but I did with this woman. Because of the policy, I didn’t ask for her phone number or anything else. I did give her my card, which has my cell and email on it; this is something I do for riders that seem like I might get repeat business from. I’m not sure if she would contact me as she said during our conversation that she prefers the man to pursue the woman.

Besides what she told me during our conversation, I know her name and where she lives. Is there any acceptable way to reconnect with her? It seems a little creepy to show up at her house or message her on facebook or other social media.

[April Masini]

Wow — that’s a tough call because your job disallows you from contacting passengers for dates — and that’s exactly what you want to do. 😉 If you really want to be bold, you could ask your company if you can date a former passenger, if you quit. Definitely clear it with them, so you don’t end up in violation of an agreement you had. And be upfront. As much as you’re interested in her, you don’t want to wind up on the wrong end of a law suit. But quitting to try and get a date with someone is pretty extreme. You could just wait and see. After all, she’s got your number, and if she’s as interested as you are, she’ll find a way to reach out. Otherwise, consider any part of the conversation in which she might have mentioned things she likes to do or places she likes to frequent. Those might be clues to help you hang out at a restaurant she mentioned or a park she said she likes. Definitely don’t take it to the stalking level — especially since you know where she lives. But if you bump into her at a coffee shop near her home or see her at a mall near her neighborhood, that seems like it’s fair game to say hello and get the ball moving. 😉 It sounds like your company is okay if someone asks you out, but not the other way around, so if there’s any way to put yourself into that situation — long shot that it is — that’s your best outcome. 🙂

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