What would you do if one of your coworkers was going through a divorce and emailed the entire company explaining her new living situation, and then asked for money and giftcards to help her through her difficult time? It’s a pretty small company, but still!
Well, if it were my company, I would have a serious talk with her about boundaries, appropriate use of company email, and, if there weren’t already one in place, immediately institute a NO SOLICITATIONS policy for my employees.
Otherwise, if I have to be honest here, what I would do is talk about how crazy she is behind her back.* I’d also pretend I never saw the email. The whole situation is weird and she sounds a little unstable. You can definitely sympathize with her and take her to lunch if she needs a friend to talk to, but getting her a Target giftcard and leaving a $20 on her keyboard will just encourage inappropriate behavior, and the next thing you know she’ll be passing around a hat, taking a collection for her boob job.
*Please note: I’m not advocating talking about people behind their backs…but you asked me what I would do, and unfortunately, I would totally do that.