Kate Bolick Was My On-Call Dating-Advice Guru

Photo: Silver Screen Collection/Getty Images

My closest friend is one of those people who is somehow, mysteriously, always in a relationship. We meet every few months for brunch/lunch/dinner when one of us is passing through the other’s city, and every time, somewhere between Alcoholic Drink No. 2 and Plate of Food No. 1, she’ll say, Allison, tell me a story. Which really means, Allison! Tell me — a happily coupled-up human — another one of your hilariously bad dating stories; and I oblige, animatedly recounting the nightmare that is being “a single Brooklyn gal who dates in 2015.” And then we laugh and laugh, at my hilarious life.

In the two years since my last relationship, I’ve developed the habit of performing my dating life as a one-woman show. I seek out the wrong, the weird, and the unholy for the sake of keeping things interesting, and then I take all those crummy experiences and use them to play up this hot-mess persona. It gets me laughs, chuckles of pity, the occasional setup with someone’s “nice friend,” and a love life that looks something like this: a polyamorous juggalo; an anarchist bike messenger who admitted that he might have killed a guy; a SoCal record producer who loved the affirmation “That’s sick!” so much that he was prone to exclaim it mid-coitus. And folks, those are just the highlights.  

Recently, however, as I’ve been considering pursuing actual relationships, I find that the more I treat my love life like a punch line, the more the line between “happy single Allison” and “hot mess Allison” blurs, and the more I chip away at my actual self-confidence and well-being. I was always certain that when I was ready to start doing some healthy, normal, non-demented dating, all I would have to do is flip a mental switch. But after two years, I’ve begun to worry that the joke is on me, and eventually I really will be all alone, still telling the story of “That’s sick!” Chris to my taxidermied cats.  (They’ll always listen, even when everyone else stops.)

The writer Kate Bolick might be the best possible spokesperson for a romantic life that’s neither man-dependent nor comically absurd. Her 2011 Atlantic cover story “All the Single Ladies” asked what happens when women no longer need, or want, or find themselves able to structure lives around permanent coupledom. Spinster, the book she published earlier this year, described her own experiences in this new world. Reading Spinster was like getting a warm hug — finally, some reassurance that even I might be able to successfully navigate single life without drama, tragedy, or horrendous sexual encounters.

In the spirit of Advice Week — and in order to stop acting like my love life is a sitcom pilot — I decided to spend a weekend treating Bolick as my personal guru. Every decision I made, I’d text her first. (Luckily for me, a mutual friend put us in touch.) We would discuss my problems, and I would attempt to embody her ideal of independent modern womanhood.

Is it even possible to learn that in a lifetime, let alone a weekend? I was willing to try.


Before our weekend of advice begins, Kate and I meet for lunch so she can get my background. She is almost certainly the most attractive person I’ve been on any kind of date with in the last year, and I suddenly remember what it’s like to be excited about meeting someone new. Jesus, I think, I definitely need help. This artisanal advice could not come sooner.

In person, she’s like every camp counselor/older cousin I’ve ever idolized — affable, confident, sharp-witted, and decisive. I like her immediately and I trust her with my woes even though I find it very hard to imagine her struggling with being single, because she’s a dead ringer for Jenny Lewis. (Indeed, as she describes in Spinster, at times she has had to struggle to stay single.)

Over lobster rolls, we go over my dating history and my current dating life. She asks things like what kind of girlfriend I am, what my friends are like, how often I go on dates, whether I want to get married or have kids. It’s a quick lunch, just under an hour, but man, do we burn deep. After our first meeting, she’s already infused me with good advice: I need to remember I’m an attractive human and to be out in the world, not on OKCupid. She also decides that, in our advice exchange, her goal will be to steer me in the direction of making decisions that make me feel empowered, confident, and in control. Can you agree to that challenge? she asks. I agree, of course, because I love her.

As we prepare to part at the end of the meal, a bride and groom walk into the restaurant. They were literally just married: She’s still clutching her bouquet. I look at Kate. Kate looks at me. The meaning is clear: Kate Bolick’s advice is going to get me married by the end of the weekend.*

Dilemma 1 

In order to make the most of my bespoke advice services, I’ve lined up a date for the evening. But first I want to warm Kate up, so I ask her some softball questions: The salon is booked — should I trim my own hair? (Yes! Snip away!) Should I buy a leather shirt? (No!) And then, one real question. I took a screenshot of a particularly bumbling text exchange with my date. I sent multiple texts in a row to solidify our plans for the night. He responded with quick one-word responses, e.g., “sure” and “k.”

Kate’s Answer 

I’m a straight texter — I don’t believe in phone calls because I’m a millennial and don’t even really know how to answer the phone when it rings. My reliance on texting back and forth (nervous chatter) to build “intimacy” usually leaves too much room for obsessive analysis and leads to one-sided microdramas. It’s very entertaining for me but not useful.


She was right. I set up a text pattern that I immediately found annoying. I spent too much time trying to decipher the “kk” and the “sure.” (Was he already embarrassed by my laptop bag? Was he irritated because I said “shoot for six” instead of “definitely be there at six?”) And then, we had like 50 other logistical exchanges before I even arrived.

After one exchange with Kate I was already becoming co-dependent.

Dilemma 2 

I’m on the date (in my bridal lace): a rooftop party with DJs and free beer. It feels more like a group-hang than a one-on-one situation and I find myself flirting with one of my date’s friends. Is this okay? I think it’s probably not okay, but I check in with Kate.

Kate’s Advice 

I suppose a part of dating is activating what makes me fun and friendly. Once you start a fire, it’s hard to contain it, am I right? Probably not, but Kate was.


I’m probably a bad flirt, but I think it just came across as me making an extra effort to be friendly.

Dilemma 3

Things are feeling a little awkward. Should I suggest smoking the joint that I have in my purse?

Kate’s Advice


Good! My date loosened up a bit and took me aside to watch the sunset. We had a “genius” conversation imagining what Bill Clinton’s First Husband duties will be when Hillary becomes president. The convo was so genius, I even took notes for later:

Dilemma 4
Without asking Kate’s advice, I left the party on the early side to meet other friends, and I was feeling uncertain about the decision. My date knew I was going but didn’t walk me to the elevator. It was a pretty awkward farewell. How can I ensure he will ask me out a second time?

I told her, truthfully, that I wasn’t really sure, but would be happy to try date No. 2 to see if there’s more of a spark. Also, I admitted, I would like him to be sure that he’s into me, even though that makes me an ego-monster.

Kate’s Advice


Not great. He responded with a HAHAHA. Maybe I got him too stoned.

Dilemma 5 

Saturday morning, I sent some date-recap texts to a friend before I Dialed-a-Kate. I will admit that I played up some of the nightmare aspects. (Really could have just said it was fun but no spark instead of EVERY DATE I GO ON IS A NIGHTMARE, but old habits die hard.) After laughing, my friend said, “Sorry you guys didn’t vibe,” which immediately sent me into a “How do I make us vibe?” tailspin. Fearing a dumb decision, I asked Kate how I could repair my faux pas of the night before.

Kate’s Advice


I actually felt pretty good about my decision to leave and not really follow up. What’s the point in being trapped in a dating cycle if I’m not interested in the person? To escape loneliness? That’s why I’ve spent time cultivating my relationship with my bodega owner. Also, my maturity had resulted in a Kate Bolick gold star. She was “glowing with pride,” she texted me. But am I only so confident in my decision because I have another person to provide me with ego-boosts? Who cares, this rules.

Dilemma 6 

It’s a Saturday night, and my friends are planning a group outing. I’m not really sure if I want  to go. Over lunch, I’d explained to Kate the slight crisis in confidence I’m having this summer. I feel, in short, like a troll who only attracts loathsome men. My feelings have been aggravated — irrationally so — by the fact that I have an insanely beautiful friend who tends to attract all the men without trying, including ones I would like to attract. I text Kate, “These days whenever we go out, it feels like this (Me on the left):”

Kate’s Advice

She had some simple advice about reversing self-imposed trolldom: “Whenever I hear myself telling myself I look bad for whatever reason, I try to flip it around and say, ‘Wait. What if you DON’T look bad. What if actually you look good? How about let’s just assume for five minutes that you look good,’ and then I feel a little better and forget about it.” Which I will try.

She also gave me permission to pull back from my pal a bit and hang out in a scene where I’m not prone to comparing myself to someone so close to me. She reminded me that it happens to everyone — even her. I shouldn’t feel guilty, she said, but I should have an honest talk with my friend to clear up any resentment.


I never did have that conversation, but I did skip group-karaoke night in exchange for going to a party with a different group of friends. Honestly, it didn’t make me feel more confident. I felt pretty guilty. Her first piece of advice was helpful, though: I spent one day telling myself I looked awesome and I noticed other people notice that I am, in fact, not a troll. 

Dilemma 7 

It is Sunday. I barely need Kate’s advice since I’d been so well-behaved. But even after the best, most empowering weekends (like this one), Sundays can be a little lonely. Normally, I would spend the day enjoying Netflix and perusing Tinder to line up a full week of disaster dates. But this Sunday I have Kate. I ask her: How do I beat the Sunday Sads in the face of all the brunching couples?

Kate’s Advice

Part of refusing to invent new and weird ways to set fire to my love life meant that I needed to be comfortable with what remained once I got rid of energy-sucking distractions — me, myself, and a copious amount of free time.


I followed Kate’s prescription for a solo Sunday. I was a little bored, but it was kind of nice, because for the first time in months I wasn’t wrought with an emotional or physical hangover.  And, per Kate’s advice, I stayed off of Tinder. 

As I entered Sunday night, I was terrified of losing my oracle and I wanted to ask her a million questions. (How should I respond to this guy on OKCupid? Should I ask my friend to set me up with her Mark Ruffalo look-alike co-worker or is that weird? Are you sure I’m not a troll?) Instead, I asked her the question I’ve had since reading “All the Single Ladies” back in 2011.

Final Dilemma

“What’s the prognosis?” I wrote her. “Am I going to die alone?”

Kate’s Prognosis

Here’s what I learned from 48 hours of advice dependency: Kate Bolick will probably be the best date I will have in 2015 (sorry, anarchist bike messenger). And we’re all going to die alone, so I should probably stop worrying so much about it and live my life with the knowledge that I’m a fun and decent person, with good hair.

For the most part, I’d refused to treat my dating life as a hot-mess shtick, which ultimately meant I had more energy to enjoy being single. Following Kate’s advice — no Tinder, no OKCupid, no texting my friends “listen to this nightmare,” no texting back-burners for ego-boosts, no socializing in situations where I felt like less of a person — I was a full-on Spinster. And I didn’t hate it.

* This is not what it meant at all.

Kate Bolick Was My On-Call Dating-Advice Guru