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  • Kristan Higgins

Advice to the Lovelorn Hipster Female

Updated: May 3, 2022


How cute are these two? Not going down in flames!

One of my most favoritest things to do in the entire world is eavesdrop on first dates. I cannot adequately describe my love of this activity, which irritates my husband for some unknown reason…he gets a rather constipated look on his face when I interrupt his poetic waxings on the New York subway system to whisper, “The date behind us is going down in flames!”

Hey. It’s how I make my living, pal.

At any rate, as the veteran of many Harriet the Spy/Dating Editions, I have some advice for you young people, you hipsters, you kids, you. This comes from the (cough) vast wisdom of one or two relationships that ended in a torturous, agonizing, drawn-out manner; a subsequent bolt of lightning kind of meeting resulting in a six-week courtship and 25 subsequent years of happy marriage; and fifteen years spent as a writer thinking about lurve. This advice is for you, my dear fellow women. Yes, just women, because who knows what guys are thinking? Probably about how great the subway system is.


Stop trying so hard to make a guy like you. This doesn’t mean you shouldn’t try to present your best self. It means you are not a product to be sold. If he likes you, you’ll feel it. If he doesn’t, it’s not your job to change his mind. You have many lovely qualities, sweetheart. If he doesn’t see them, move along.

“Let me tell you about my ex.”

Stop talking about your past relationships so much. Save this for…oh, let’s say your tenth date, okay? Not the first! If I were a guy trying to see if I liked a woman, I wouldn’t want to hear about how her ex failed her, lied to her, disappointed her. In fact, I would imagine this guy’s testicles would be shriveling as you detailed the shortcomings of your ex, and/or he’d thinking about a beautiful subway system somewhere.

Don’t try to control the conversation. This includes things like interrupting, speechifying and dismissing. Sure, you have many thoughts to share, but this is not the You Show, starring You. This is a date. You’re exchanging words, not just delivering them. Of course you are smart and passionate, but…come on. I overheard one guy say that he thought Breaking Bad was the best show ever (I concur). His date’s response: “Clearly. We don’t even have to discuss it, it’s so obvious. Next.” Sweetie? He wanted to discuss it. Why’d you have to be so rude?

Don’t waste your time. If the guy says something that’s truly offensive (racist, sexist, homophobic, etc.), tell him you don’t wish to spend more time with him and leave. Don’t worry about being nice to a person who is, let’s be blunt, an ass-hat.

Don’t sleep with someone on the first date. I know, I know. It’s 2017 and you’re a powerful woman who’s fully embraced her sexuality, but you’re looking for a spouse, remember? Not a human vibrator. Show this guy that you’re worthy of an investment of time and thought. Remember, you want a relationship, not a hook-up.

Be open to the people who might not seem like your type at first glance. Talk to the guy before you meet. Don’t rely on texts or messages. Use those vocal cords. Skype or FaceTime, even! You may quickly realize that this is a nonstarter (see #4). Good for you! You didn’t waste your time!


Or, you might find that even though he prefers cats to dogs and didn’t care for Breaking Bad (freaky, but not sociopathic), he might be charming and interesting in his own way. I never thought I’d marry a blue-collar guy who was younger than I am, didn’t go to college and—horrors—STILL is unsure about the proper usage of the words went and gone.

But I love him like crazy just the same.

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