What is the protocol for asking one of my clients out on a date?

We’ve kinda been flirting for some months now, I think he likes me and I know he’s not seeing anyone, Furthermore, I suspect he’s been holding back because of the nature of our business relationship and he doesn’t want to risk impropriety.

answer:
A wise policy. Dating clients is even more fraught with danger than dating co-workers because if it all goes south, your business could end up suffering. This is dangerous territory and I caution against venturing here. Perhaps you are reading his reticence as something it isn’t. Perhaps what you see as flirting is merely him being overly pleasant. Two words for you here: Thin ice.

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