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Can I Ask My Boss Out For Valentine?

My boss posted on her WhatsApp story “Who will be my Val” and other series of messages concerning taking her out for Val.

I’m older than her and she respects me, deep down I really like her, I don’t know if I should ask her playfully, we chat a lot. I tease her a little bit when she posts a picture that is not fine and we laugh over it.

I want to tell her if she is unsuccessful in her search for a date I can be her back up plan. I don’t know if it’s a good idea to tell her that. I need honest and matured opinions please.

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