Asking Out a Co-Worker

“Hey Brian…” is a weekly advice column on workplace situations written by Brian Stiglitz. If you have a question for Brian contact me at You can also see Brian in action on the Full Disclosure YouTube channel and follow Brian on Twitter @stiglitz_b.

Hey Brian,

I’m very attracted to one of my co-workers, whom I’ll call Sheila. She is friendly toward me and we have had some pleasant conversations and she has said that she thinks I’m funny. I’d really like to ask her out on a date. However, I know that workplace relationships can be tricky; I had one go south at another company and it created problems in the office. Still, I really like her; I’m just not sure how to approach the situation. Should I email her with a suggestion that we grab a drink after work sometime? Should I just flat out ask her to dinner? Or do I play it safe and look for love elsewhere?

Pining in Pittsburgh

Dear Pining,

Yes, workplace relationships can be complicated. Many companies have policies that explicitly forbid dating among co-workers. Whether that is true at your place of work or not, you need to be careful about it. Here are some things I have done in the past to woo a co-worker.

Ask her if you can borrow some money, maybe forty or fifty dollars. Give her a story like you are going to visit your sick mother and you want to pick up a gift for her on your way to the hospital. However, your bank card isn’t working and you don’t have any cash (you could also tell her that you lost your wallet or something) and the gift would really mean a lot to your mother who might be “on her way out”. The hook is that, after she loans you the money, tell her that you will take her out to dinner to pay her back.

This strategy works on a few levels. One, it shows you care about your mother and that is very attractive to females. Two, you can get dinner with “Sheila” but it’s not a date because you are paying her back so no policies are being violated. Three, if she declines the dinner chances are that she will let the fifty dollars go and you won’t have to pay it back.

If she will not lend you the money, that tells you all you need to know about her character and she isn’t worth your time anyway. What kind of person would refuse to loan a guy fifty bucks to buy a gift for his sick mother?

If the money angle isn’t for you, there are other ways to let her know you are interested. Leave the office a few minutes before she does and wait for her at her car. Do this a few times a week. At first, make like it’s a coincidence. Make conversation to get to know more about her interests and what she does in her off hours. Women like a man to be interested in them as a person and not be so self-involved. Gradually, she will become more comfortable with you. Then you can start asking her more personal questions. Ask her where she lives. Does she live with anyone or does she live alone? Ask her if she is divorced and, if she is, ask her why she got divorced. Ask her what route she takes to get home and if she takes the same route every day. Ask her where her parents live. Ask her if she has any children and if she doesn’t, ask why not. Ask her if she uses a home security system. Let her know you are interested.

Women like a man with confidence. Find out where she might be having drinks with friends after work and show up there. Act like it’s a big coincidence and invite yourself to join the group. Make yourself the life of the party. She will admire that. You can meet some of Sheila’s friends and ask them questions about Sheila’s personal life. Tell them, with Sheila listening, what she eats for lunch and that her diet has really helped her keep her weight under control.

Say something like, “Sheila hits that bathroom everyday right at 1:10. Like clockwork!”

You’re paying attention; you’re interested.

Find out where she goes to the gym and start going there. She’ll feel more comfortable in a non-work setting.

It’s easy enough to get her mobile phone number from someone in the office. Use a ruse like, “Oh damn, I missed Sheila and I need to let her know about part of the project we are working on!” If you insinuate that Sheila really needs to know about it or she will be in hot water with the boss, someone will give it to you. You can also try to get a look at her personnel file but that can leave a trail which would be difficult to explain.

Once you have her number, you can start texting her. Start with work matters and then little jokes about the office. After a while, start texting her away from work and make the texts more personal. If you text her later in the evening, she might be in bed which creates a more intimate situation. Ask her if she prefers showers or baths, what kind of moisturizers she uses etc. Ask her advice on what you should wear to work the next day. If she seems put off and does not respond to your texts, that is perfectly normal. She needs time to get used to it. Don’t be afraid to be more forceful; keep texting her.

You might want to hint that if she does not go on a date with you that there might be trouble. Be careful how you phrase it though; you don’t want a legal hassle.

Good luck and Happy Hunting!



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Matty Kerr

Matty Kerr

Co-creator and cohost of The Working Experience Podcast. We explore what people do for work, how they do it and how they feel about it. Twice a week!