Is It Sexual Harassment to Ask Out a Waitress?

And other questions for Persuasion's advice columnist.

Is it sexual harassment to ask out a waitress? Since #MeToo, I’ve had the impression that women feel constantly sexualized, and that approaching them in the workplace is inappropriate. But outside the workplace, it seems as if the only way you can do so without being creepy is via a dating app. What should I do?

Here’s the bad news: There are women out there who find it so burdensome to say no to a man who doesn’t interest them that they consider any overture, no matter the context, content, or intent, to be a form of sexual harassment.

The good news is, these women are silly and very much in the minority. And while smartphones have made it possible to only date in the “opt-in” environment of AppLand, it’s much too soon to declare that this is the most effective way to make a successful match, let alone to decide that every relationship in human history pre-2008 must have been creepy because the people involved had to approach each other in person. (One might even argue that the absence of accountability in the form of a shared social network enables guys to be creepy on Tinder in all kinds of new and horrific ways they’d never dream of in other settings!)

As for approaching women at work, that’s a little more complicated. Baristas, librarians, and the like have to be friendly, and as a result, they field a lot of gross behavior from customers who a) can’t tell the difference between professional friendliness and flirting; and b) won’t take a polite no for an answer. That said, if you feel compelled, you can’t go wrong with a short, sweet, handwritten note. It should include:

1. Your name;

2. Your phone number;

3. An invitation to text if she’d like to get a coffee sometime;

4. A solemn promise that this is a one-time, no-pressure overture on your part: If she’s not interested, then as far as you’re concerned, it already never happened. You’ve gotta say this, and you’ve gotta mean it — and if she calls you, then, hey, you get to be pleasantly surprised.

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Need sane advice for an insane world? Send your questions to Kat Rosenfield at persuasion.advice@gmail.com. We will of course preserve your anonymity.

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Should my parents have a veto on my friends? I (25F) have an online friend (36M) of four years whom I’m planning to meet for the first time. We’ve had tons of face-to-face calls, and he’s amazing and incredibly supportive, so I have no worries. But my parents don’t like that he’s older. I live at home because of my anxiety, and pay for myself. I’ve thought about asking them to meet him. But what if they still don’t like him?

I can’t help noticing that you’re in a bit of a catastrophic mindset here: convinced that your folks will react badly, and that you’ll be unable to handle it when they do. It makes me wonder how much your anxiety is exacerbated by living with people who punish you by withholding affection every time you make a choice they don’t like. The worrisome thing about your letter isn’t that your parents don’t like this friend they’ve never met; it’s that you are 25 years old, and still trying to manage their feelings at the expense of your own.

So rather than looking for ways to manage their feelings, I’d like you to think about ways to make yourself okay with living your life irrespective of their opinions. A good start would be to schedule your meetup without asking parental permission, and then present your plans as a fait accompli: “I’m heading out later today to take a walk with Bob.” If your choice of friends makes them uncomfortable, that’s their issue to deal with, not yours. And if they push back, feel free to point out that they’ve had 18 years and then some to raise you to be a self-sufficient adult—now is the time for them to trust that they did a good job of it, and let go.

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Should I fire my QAnon-supporting babysitters? I didn’t vote for Clinton or Trump, and I’m a minority in my community by not voting for Trump this year. But two of my childcare providers have come out as QAnon supporters, and said on their Facebook pages that anyone not voting Republican does Satan’s work. This a slap in the face to me, who is deeply pro-life, has been a foster parent, and counsels young teenage moms. These babysitters are wonderful people otherwise, and I believe their motives are fear. What should I do?

For starters, please resist the urge to take other people’s bizarre beliefs personally (“a slap in the face”). If you were walking down the street, and passed some wild-eyed guy holding a sign that said, “YOU ARE ALL LIZARD PEOPLE,” would you feel accused? Or would you think, That guy has issues? When your babysitter posts on Facebook that anyone not voting for Trump is in league with the devil, she’s not saying anything about you. She’s just announcing to no one in particular that she is a certain type of crazy person. 

The real question is whether, knowing that she has these beliefs, you still trust her to care for your children. On the one hand, you don’t want to worry that your kids are being indoctrinated with Pizzagate conspiracy theories every time they spend time with her. On the other hand, people can believe all kinds of silly, counterfactual, or even dangerous things without posing a risk to those around them. Would you feel so gutted if you’d learned that your sitter was a devout Scientologist or an alien-abduction truther? Is she a good person who has bad ideas? Or do her politics speak to bigger, more troubling issues with her judgment? If it’s the former, maybe you can tolerate (or ignore) her obnoxious Facebook posts for the sake of preserving the relationship. If the latter, maybe you’ll want to push back or cut ties.

Kat Rosenfield is a culture writer and author of several novels.