PHOTO: Stewart Scott-Curran/CNN

Story highlights

Ann Colwell found an online date went south when her suitor lobbed a compliment that landed flat

She commiserated with other women who also weren't sure how to answer backhanded compliments

Etiquette expert Lizzie Post says explaining that a comment rubs you the wrong way is OK

(CNN) —  

Halfway through a recent first date, my latest Tinder suitor — let’s call him Heath — interrupted the conversation, apologizing.

“I should have told you this when you walked in,” he said. My stomach tightened, anticipating what a man might preamble with those words. “You look really nice tonight.”

“Oh, that’s so nice of you to say,” I said, smiling. “Thank you.”

“I was really excited to go out with you,” he continued. “You seemed so interesting and smart. I feel like it’s so rare for me to think a girl’s smart.”

I grabbed my drink and nodded stiffly, unsure what to say.

“I guess what I mean is, I just don’t find that many girls as intelligent as you,” he barreled ahead. “It’s really nice to talk to someone as … well, someone as smart as me.”

I shifted in my seat. Is it just me, or was that really sexist? Does he not realize that?

What am I supposed to say? I thought to myself. I know I’m smart, so why does him saying that make me uncomfortable? How can I agree or even accept the compliment without insulting the rest of womankind?

I didn’t know what to say, so I said nothing, and ordered another drink. But Heath’s comment got me thinking about what to do when a likely well-intentioned compliment falls flat, leaving me speechless, or maybe even a little insulted. If a compliment lands on me in a truly uncomfortable way, is that my problem or his? How am I supposed to deal with it?

“It doesn’t matter whose problem it is, because it’s a problem you’re now both dealing with, and you have to decide how you’re going to react,” said Lizzie Post, author and etiquette expert for the Emily Post Institute.

“Sometimes it’s as easy as letting the person know he’s not having the right effect but you’re willing to let them try again,” Post said. “It’s OK to just call them out on it and give them the benefit of the doubt. You’re letting them know that they can keep talking, and we’ll try again.”

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Great advice, but perhaps easier said than done, especially for an apologetic, good-natured Midwesterner like me. Besides, it’s not that I don’t like being complimented. I love compliments! Please compliment me, especially if you are trying to win me over.

But, is it possible to avoid saying nice things in a smug, heroic tone that simultaneously insults other women? And, if I’m not asking too much, maybe give a compliment that doesn’t belittle me?

Granted, the line between a compliment and an insult is different for everyone. For me, I’ve got to draw it at accidental jabs at my appearance, and insults to other women. So how should confident women deal with backhanded comments and the men who lob them?

Feeling defeated

The dilemma came up again a few days later, when Heath texted to ask if I’d like to go out again. Aside from his backhanded compliments, I liked him. I said yes, but it would have to wait. I’d come down with the flu.

“I’ll make you feel better,” he wrote. “You looked fantastic last week.”

Enough! I thought. You saying I’m pretty won’t cure the flu!

But I didn’t say that to Heath.

“Thank you (smiley face),” I wrote, feeling a little defeated.

Dating in the digital age

You might be thinking I’m some demanding millennial with an exaggerated ego. Judging from conversations with friends, it seems that I am not the first woman to struggle with these social quandaries. And, thanks to the Internet and social media, I know we are not alone.

Earlier this month, author Roxane Gay tweeted a series of observations from her own experience:

“Man on the street just told me I have a pretty face and I shouldn’t let anyone tell me I’m fat. Ummmm,” she tweeted.

“Thanks for that unsolicited feedback.”

The Internet also reveals the potential pitfalls of expressing some of these things aloud. In a recent experiment, several women responded on Tinder and Tumblr to messages from men that ranged from generic to slimy. The women simply agreed with the compliments paid to them, leading to some hostile responses, which completely negated the nice things the men had just said.

These, of course, are the extremes: the Internet trolls. But they show how these exchanges can start out benign and escalate into something closer to harassment, which is what most women fear. Call to mind last year’s viral video showing street harassment in New York. It’s not that all the men are saying inappropriate or offensive things. It’s that they’ve inserted themselves into that woman’s day without invitation.

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It’s important to note that the women above — who did not respond to CNN’s requests for comment — conducted their experiment online. Could and should someone like me ever be emboldened to express these frustrations in a face-to-face interaction with a potential match?

If I did, the potential real-life social risk is high. The Internet disinhibits people because the “perception of anonymity is higher,” said psychologist Patricia Wallace, author of “The Psychology of the Internet.”

It’s easier to depart from social norms online with strangers “because if they form a bad impression of me, who cares?” Wallace said. “You’ll never see them again.”

But, “impression formation” matters in real life, where you have a chance of meeting someone again, whether it’s a co-worker or a suitor you don’t care for, she said.

The benefit of the doubt

Even when it comes to the canned opening lines pervasive in the online dating sphere, some experts advise that unless it’s so crude as to offend your sensibilities, try to take it for what it is: a compliment.

“His aim is not to inform you, belittle you, or treat you like you’re stupid,” said Sharon Andrea, dating coach and founder of Modern Dating Mastery. “He’s not sharing news. On the simplest level, he’s saying, ‘I want to connect.’ “

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Which brings me back to Heath.

Our second date was unremarkable. He filled the time with nervous chatter, and I left relieved that I didn’t have to field more bizarrely insulting praise. We didn’t go out again.

But Heath was not the first and he won’t be the last to give me a compliment that went wayward, leaving me wondering how I could have handled other situations differently.

To the man who told me he was relieved I wasn’t “a fatty,” perhaps I’d say that while I appreciate that he finds me attractive, that’s a nasty word I’d rather he didn’t use to describe anyone.

To the acquaintance who told me he’d ask me out if I just gained the oddly specific figure of “12 pounds,” I’d want to clarify: Was that supposed to make me feel good? Because it didn’t make me feel good, and it might be better to avoid criticizing a woman’s appearance, no matter where she stands on the spectrum.

And to the next well-meaning Heath, I think I’d take Post’s advice and say: That didn’t land quite right with me, but I appreciate that you find me engaging. I’ll give you the benefit of the doubt, and we can try that again.