Is it okay to ask a woman out while she’s working?

Dear Lisa,

I am curious about someone who works at a place I go fairly frequently. My first question is that I’m not sure if the curiosity has a romantic component or not and I want to know if it is bad policy to pursue her, even if I’m not sure I’d want to date her.

Second, what is a socially acceptable / professionally respectful way to ask this person out? I’m not used to approaching people at work and wonder what the etiquette around this might be.

–Patron (♂ Victoria)


Dear Patron,

To answer your first question, I see dating as the way individuals get to know each other and see whether they are compatible for a longer term intimate relationship. I think it’s a great idea to go out a few times to see if there is a spark, and if there isn’t, just let her know that you aren’t feeling it.

Where things get complicated (especially for most women) is when the relationship moves beyond getting to know each other and into deep intimacy and sex before any discussion of intimacy. Avoid that and you shouldn’t get yourself in any trouble 😉

With regards to asking her out in her place of work… just like the ‘how do I avoid being creepy’ question, the whole socially / professionally respectful thing is complicated by two things – whether she is attracted to you, and the appropriateness of the situation. If she isn’t attracted, then anything you say or do risks offending her. However, if she is attracted to you, then pretty much anything you say will be fine, unless you do something inappropriate, like act arrogantly, look spastic, ask her in front of her boss or corner her when she’s alone.

Obviously, the first thing you want to do is try and make an accurate assessment of whether she is actually attracted to you, or just nice to you because it’s her job. A few things to consider would be prolonged eye contact, blushing, smiling, hair touching, whether she acts more feminine (could be shy, could be chatty) when she knows you are there, and perhaps whether she offers you details about herself and personal life. If you are seeing her do more and more of these things, you’re probably good to go.

The best way to handle an at work situation is to approach her before you leave (this adds a little mystery if she says yes, and gives you and her some space if she says no). In your approach, make it clear that you are aware of the potential awkwardness by being brief, approaching her when she’s not busy and more or less alone, and respecting her personal space, time and decision. During your conversation, make a conscious effort to keep an eye on her body language – if at any point she tenses up, her eyes get wide and then look away, or she moves any part of her body away from you – abort mission and go back to step one. Keep your words simple; after breaking the ice just let her know you’d like to get to know her better and if she’s interested, you’d love to take her number and give her a call.

Equally important as respectful behavior and awareness of her comfort level, is not being wishy-washy or apologetic. It’s easy to make the mistake of nervously talking about how awkward it must be to be approached at work and how you understand that she might not be into it, and that you won’t be awkward later, and that you’d even avoid coming in if that would make her more comfortable. Not only does this make you seem uncertain and less manly in her eyes, it can make her wonder if you are indeed a creep.

Finally, if she says no or that she’s otherwise engaged make it clear that you get the point: thank her for her honesty and say that you understand. Next time you are in, do your best to act as you normally would and things will quickly return more or less to the way they were.

I’d love to hear how it goes!

– Lisa



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