I currently work with a woman who recently broke up with her boyfriend. Last year she thought he might be cheating on her and when she confronted him about it, he denied everything. She trusted him and let things go on, however last month, she found out the truth and broke up with him — she is completely heartbroken.
The few months leading up to their split, she would talk to me everyday about her situation; she'd ask for my advice, she'd ask for my support, and it seemed like she genuinely enjoyed my company. Nothing ever happened between us, but now that she is single again, I was wondering if you think it would be a good idea for me to ask her out? — Proceeding With Caution Chris
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Dear Proceeding With Caution Chris,
You say your co-worker is heartbroken, so while she's technically fair game, I'd give her a little time to mourn her failed relationship. In the meantime, continue to be her friend, but make sure you don't take on the role of her new best girlfriend — make subtle hints here and there to let her know you're interested in something more, but I advise you not to ask her out just yet in case she's not ready to be back in the dating scene again. Keep feeling out the situation, and when the time is right, I say go for it — ask her out — you have nothing to lose! Good luck.