Years ago, I worked under a captivating female boss for about 5 years. Even though I was married, I couldn’t help but imagine what it would be like to date her. 8 years later, we’re both on different paths and haven’t kept in touch, until one day she surprised me with a LinkedIn message inviting me to lunch.
This unexpected turn left me bemused – why would she want to catch up after all this time? Still, curiosity got the better of me. The meeting was a pleasant catch-up, filled with updates, gossip, and reminiscence. As the bill came, she insisted on paying, ending the gesture with a cryptic ‘you pick up the next lunch.’
So, it seems there’s a ‘next lunch,’ but I’m puzzled. She’s successful, in a higher position than I am, and well-connected. Professionally, there’s nothing she needs from me. We worked together, but we never dated, so I’m not sure why she’d want to rekindle this connection. She’s attractive and could have anyone, including younger men.
So, Reddit, what’s the game here? She’s indicated she wants to ‘do it again,’ but what’s her motivation? Is it possible she’s seeking more than just a friendly lunch? I don’t want to jump to conclusions or ruin this unexpected rapport. What’s your take on this?

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