Thoughts on approaching women in the workplace

I only really have two life updates that I’m going to get out of the way before I delve into my topic of choice today.  I interviewed for two promotions and unfortunately did not get either, but I did put in for a reassignment to a new location and I do think I’ll get it and with that relocation more experience that will help me with promotions in the future.  Now that the boring stuff is out of the way, on to the interesting stuff.  Approaching women in the workplace…

DISCLAIMER: What follows is of course filtered through my life experiences and those of close friends/relatives.  It will not apply to every situation, but I think it’s a pretty solid start.  As always YMMV.

The entire discussion came up because my sister and I were talking the other day about getting hit on at work.  We have both been in this uncomfortable situation so we thought we’d share our experience.  This is a broad topic so we’re going to narrow things a lot: How to approach women in the customer service industry when you are the customer.  (I’m focusing on women in customer service because I am one and I don’t presume to understand the complex and different cultural conditions around being a guy uncomfortably hit on in the work place.)

The short answer is don’t.

In general people in the customer service industry are being paid to be nice to you.  Any interest you think you’re sensing from her should be seriously taken with an entire block of salt, because again, they are being paid to be nice to you.  They can’t turn you down bluntly because if you decided to take offense as a customer it could be used to discipline them unfairly.

Well, you say I’ve had some conversations with her and I actually do like her, she’s pretty and seems interesting.  It’s unfair to say I can’t ever hit on her.

Ok, fair enough.  Maybe you’re a regular in the coffee place, restaurant, store, etc. and you and she have had some good chats.  You feel like this could really go somewhere and you don’t want to waste the opportunity.  That’s cool, you probably can’t really run into her anywhere else without becoming a stalker (which is a bad no-no, don’t do that) so her place of work is literally the only place you can see her at and thus is your only opportunity to ask her out.

I feel you there so let’s lay some ground rules:

Women in customer service get hit on…often.  There are scores of people who think that since they have a few sparse conversations with a woman in the workplace they know her very well.  They do not.  Please never fool yourself into thinking you know her well because she shared what her college major and favorite band/tv show/book/author/whatever are.  These are things she’s decided are safe to share, they aren’t intimate or even particularly deep details unless she’s gone on to outline some complex life plan or crazy fandom theory that actually counts as something people judge you on.  And even then it depends on the woman in question.

If she says no and doesn’t give you a reason, DO NOT PUSH FOR ONE.  It’s her right to say no.  She doesn’t owe you a chance, no one owes you anything.  She might have a rule in place that she doesn’t date anyone she met at work (That was my rule of thumb, broken once to disastrous results). It might seem unfair and harsh, but it’s her right to have it.

Don’t try to ask her during a stressful time at work: if she has fifty coffee orders, came back another time.  She’s trying to close up the store?  Why are you still there? Pick a better time.  Make sure it’s slow, relatively low key so she doesn’t have personal stress heaped on professional stress.

Ok, so ground rules are covered: let’s talk tips for success, which is really what this is all about.  You’ve heard everything I’ve already said, I know you have and I hope you’ve taken it to heart.  If you haven’t; start taking it to heart now.

Tip #1:  You can gauge her general interest (I can’t guarantee it’s romantic) by how many questions she asks you.  If she’s actually interested in you as a person it won’t just be a possible polite return on the questions you’ve asked her, it will be about getting to know you better and that means you might not be just a customer.

Tip #2:  Never ask her for her number.  That puts tremendous pressure on her and what if you turn out to be a creep?  BUT I’M NOT, you whine.  Don’t care, she doesn’t know that and she has every right to put her safety first.  You may be the empty chamber of the gun in Russian Roulette, but that implies Russian Roulette is a safe game.  If you want to do a number swap, offer yours first, maybe she’ll offer her’s in return.

Tip #3: If you want to ask her out, keep it low pressure.  Don’t ask her about dinner, too many expectations.  Ditto for going to a bar to get a drink after work.  Coffee is fine if you both like coffee.  Want to surprise her?  Want to actually get to know her and let her know you better?  Ask her out for ice cream or frozen yogurt.  Some kind of dessert.  Why?  Because it’s about the lowest pressure you can offer someone.  Dessert isn’t serious, it is by it’s nature indulgent.  No one is going to go to dessert and order something they don’t like because they think it’s expected of them.  You and she will both be honest about your tastes because otherwise dessert is a miserable experience and next to no one does that to themselves.  Don’t not order something, that’s just awkward.  Even if sweet isn’t really your bag there are simple flavors that I’m sure you like or find a specialty ice cream place with adventurous flavors to try.  I live near a place with bacon ice cream, trust me, they exist.  Oh and if she’s the rare breed of human who doesn’t really like dessert and she wants to go out with you, she’ll probably suggest coffee instead.

Tip #4: The second date shouldn’t be your only goal, because if you’re just worried about closing (to use a sales term) you aren’t going to be a very interesting date and will possibly come on too strong. Remember to have fun most of all, because that will be you at your most attractive.

Hopefully some will find this useful or relate-able.  Please feel free to contact me with criticisms, concerns and additional questions.  Also see hilarious College Humor video below.


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