The Ultimate Question: Fond of a Customer, Now What?

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Twice a week for nearly a year, this woman comes into the my place of employment to do business for her employer. We always hit it off, and she seems really into me but I can't ask her out because it's prohibited. We talk a lot, and share about our lives and when she leaves she always gives me this longing, almost yearning look...her voice changes and she gives me a goodbye. I know her name of course and where she works but no other contact information. Any ideas on how to let her know I'm interested in asking her out?

- Employment Crossed Lovers

Shaina's Advice: 

First of all, if your employer prohibits asking clients out, you can’t ask her out. Unless you’re looking for an excuse to leave your job, just don’t do it. Remember, this is a policy that helps prevent both employees and employers from feeling harassed.

Now, on to the stuff you can do. Magenta is right. Continue talking about hobbies that you both might enjoy. Mention events that you are already going to. Don’t scour the internet finding an event that you may like to bring her to. You’re going to paint a fake picture in your head about what the date will be like and you may end up going to an event that you didn’t actually care much about. You could say, “maybe I’ll see you there”, but I would just leave it in her court. If she wants to see you, she’ll see you.

This is a tough one because you don’t know if she really likes you back or if she’s just one of those people who’s naturally flirty and affectionate. And, you’re job is on the line if you do anything. So, leave it up to her to make the first move.


Magenta's advice: 

This one is a tricky one, because it sounds like between your workplace rules, and also not wanting to create an uncomfortable situation for a woman just trying to come in, do her employment-related business, and leave, there's not a lot of opportunity to talk about what you both may be looking for. I'd make sure your #1 priority is not making it weird for her to come in and take care of business, so however you approach talking to her, keep it light, casual, and friendly. Remember women often face men misinterpreting their politeness as a come-on, and it can make an uncomfortable situation if she's just being friendly and you're too forward. 

Have you two talked about hobbies? I'd probably start to bring up topics like books, types of events you both go do, local cafes- light, easy stuff. If you figure out there's something you're both into, extend a "maybe I'll see ya!" type of invite to an event. This keeps the ball firmly in her court, while also avoiding being explicitly asking somebody out. Make sure it's an event you're actually interested in going to, so if she doesn't take you up on the offer you're not sitting around bored and disappointed.