Ask Polly: Should I Make The First Move?

Appearing here Wednesdays, Turning The Screw provides existential crisis counseling for the faint of heart. “Because Jesus cares less than you think he does!”

Dear Polly,

I recently started my dream job, at a growing startup, with a bunch of friends I really like and who inspire me. The company is growing quickly so I’ve been on the lookout for possible fellow travelers who are cool and organized and would fit in well with my team. My best friend recently recommended a young man for the team and told me in setting up the meeting, “You”ll love him!” Which, it turns out, I do.

The company is going through some planned chaos right now, so the position I considered him for may not materialize for a few more months. In the meantime, we’ve become friends. We like a lot of the same music and art, and we’ve gone out together several times now, sometimes with others, sometimes just us. Pretty much the whole time I’m trying not to be distracted by the huge crush I have on him. I get the feeling he digs me, too. Normally I’m the sort of person who would happily make the first move, but since he came to me in the context of seeking a job, I’m reluctant. I don’t want to be inappropriate! He still needs and wants a job, but all I can think about is whether or not he wants to make out with me.

Am I being overly cautious? Or prudently reluctant? Please keep in mind when answering that I’m the type of person capable of infusing workaday situations with drama, especially in the absence of any actual drama. And that my life is going really well right now.

Overthinking It

Dear Overthinking It,

When I was young and my life was going really well, I always made the first move. I thought it passive and retro to wait. But I look back now and think that was stupid. I rarely gave anyone a chance to win me over. And sometimes after I started seeing someone, I wasn’t sure if we were together because I happened to be semi-attractive and entertaining and I forced the issue, or because that guy really liked me. I’m not sure the guy in question always knew either.

I look back now and see myself as one of those cheery girls handing out free samples of brownies and cookies at the mall. Of course you’re going to eat that exotic chunk of brownie that’s shoved in your face unexpectedly. Does that mean you really love macadamia nuts? Are you even hungry, or are you just mildly bored?

In your case, making the first move isn’t only inappropriate, but it could create a real mess for you down the line. He might seem to like you partially because he wants you to hire him. Do you want to start something with someone who could be lukewarm, or who could end up saying, “Don’t get freaked out or anything, but I hope this sleeping together thing doesn’t affect my chances, because, dude, I really need a job”?

You’re already spending time together. Eventually he’ll say something about his feelings or he won’t. If he wants the job more than he wants you, well, that’s instructive, isn’t it? He can either be swept away by his feelings for you, or he can take the safe course and therefore be safely avoided.

Many of us, when we’re young, end up following some bored, ambivalent person around the mall for hours, just because he or she deigned to eat one lousy brownie nugget. We could all benefit from a little more patience and a little more self-restraint, if only in the interest of self-preservation.


Dear Polly,

I’m 29 years old, and my wife and I have been married for two years, but we’ve been together for over a decade. For four years we did the long-distance thing, and then when she finished her medical education this past spring, we were both excited about finally living together again. Unfortunately, med students don’t just get to pick where they do their residency, and my wife ended up in Hartford, Conn., while I was still living in NYC.

The program in Hartford is the perfect environment for my wife, and she’s absolutely thrived there. I couldn’t do a long-distance relationship anymore, though — it was harder being in New York and knowing that my wife was two hours away than having her across an ocean. I quit my job in NYC, dumped the second apartment there that we were paying for, and moved in with my wife for the first time in ages. I love living with her, but transitioning to life in Hartford hasn’t been easy.

I know that plenty of people live in places less exciting than Hartford, but all of my friends (and some of my family) still live in NYC, along with the activities I used to love. Hartford has fewer than 200,000 residents, and on the nights and weekends the downtown area where we live completely empties out. I haven’t had a car since high school, and now I’m already planning which one to buy once I find a new job because the public transportation isn’t well developed.

Do you have any advice on how to roll with the punches during a major life change? It’s not just the slower pace, it’s having to transition to a new industry and taking a sizable pay cut after years of consistent raises/promotions, having to deal with the fact that my wife is constantly exhausted from 12+ hour days at the hospital and will be this way for three and a half more years, having to sit on the couch all weekend because my wife is working and I can’t think of anybody to call.

I’ve noticed that one of the common themes people write in to you with is centered on the desire to make a mark on the world and the feeling that they haven’t accomplished enough. When I was in NYC, I loved my job, I had a good group of friends, and I was generally content most of the time. Most people aren’t destined for greatness, and I was happy with happiness. I’m just not sure I can get that same experience here.

Bored in CT

Dear Bored in CT,

Being forced to move to some random spot you don’t like is definitely one of the major hazards of getting married. Small places, like three-legged dogs and babies with male pattern baldness, can take a little longer to love. I understand why you’d feel the way you do at the moment, considering the myriad glories of NYC, unmatchable elsewhere. Accepting less money and less status, missing your friends, longing for the tasty foods and the hustle and bustle of the big city, slouching around the house in your boxers, waiting for your exhausted wife to come home from her residency? These things are a recipe for depression. I’m actually shocked that the word “depressed” never appears in your letter.

I’m going to take this notable absence of the word “depressed,” add it to the remarkable restraint you’ve shown in not blaming your wife for your circumstances, and conclude that you’re a reasonably healthy human being, one with good boundaries and an overall optimistic outlook on stuff. Congratulations! Personally, at your age, I’d be talking shit about Hartford all day to anyone who’d listen (thereby alienating my few potential friends) and then lashing out at my spouse (and slowly but surely ruining my marriage) all night. If I were in your shoes, my wonderful, lovely future-doctor wife would be fucking that studly chief surgery resident by the end of the year.

So let’s build from these strengths of yours, shall we? Your career might suck for a while, but I’m sure you’ll have a lot more choices once your wife finishes her residency. One thing that’s clear, though, is that you have to get out of your apartment on the weekends, and you have to do stuff with new people. You don’t get a free pass from doing this just because you’re married. You have to go out there and be around new people and join clubs and whatever the fuck. I understand that none of these imaginary strangers seem all that great, there aren’t many fun things to do, plus the bars close down early and whatnot. Most places in the world don’t have bars that are open until 2 a.m., and only people from New York and New Orleans and a few other spots on the globe use this as some kind of rubric for judging a place’s quality. Yet the rest of us have adopted it — “Look how sleepy it is here!” — like we’d prefer for our perfectly nice towns to be overrun with theme bars and nightclubs and strip joints. Should every Bedford Falls become a Pottersville? I think not. What’s all well and good (and, yes, intoxicating and special) for NYC doesn’t really translate elsewhere.

But there are other options. A quick search on “Hartford bloggers” sent me to a blog called Sad City Hartford which is negative enough to suit your tastes, but also lists local bowling parties and other forms of weirdness that might be enjoyable now that you’re truly desperate (but not so depressed that you can’t get out the door). Email that guy who posts there, Hakaan, and offer to buy him lunch and ask him about life in Sad City.

In smaller places, you’ll have to stick your neck out, get a little dorky, show your ass. You’ll have to invite five people you hardly know out to a big tasty dinner at Monte Alban, and you’ll have to drink two strong margaritas (strong “like paint thinner, according to local reports), and you’ll have to be enthusiastic and optimistic and listen when people talk, even though they’re nothing like your friends back in NYC. You have to keep an open mind about these new people. (The paint thinner will help.) After a few weeks, you might even find yourself proclaiming, over dinner, that henceforth, Mondays shall be known as Margarita Mondays, and everyone is invited. “Bring your friends!” you’ll say in a temporary paint-thinner-fueled expansive state that you’ll regret the next morning. But then people will bring their friends, and some of them will be interesting, and slowly but surely you’ll have a life.

At the very moments when life feels the most melancholy and bereft of promise, that’s when you have the greatest opportunity to transform not only the present moment, but to expand your horizons from that point forward. My dad died suddenly of a heart attack when I was 25 years old. To say that I was crushed doesn’t quite do justice to my state. I was flattened, to the ground. I was partially erased. I flew home to North Carolina for two months. After staring at the ceiling and crying for a week, I started to spend half of my day running around the neighborhood where I grew up. I would run, then walk, then run again, covering ten or twelve miles a day, listening to music, crying. Then I spent the second half of the day working on my mom’s yard, which was a wreck. I was devastated but I was also so grateful to be alive. When the wind kicked up and it started to rain, I’d keep running or keep pulling weeds, and sometimes I’d cry. I had no skin. There was no boundary between me and the rest of the world. I could soak the whole world into every cell. I was painfully, exquisitely alive.

That example might feel out of scale here. What you’ve described is dissatisfaction and distaste, not grief — again, you didn’t even use the word ‘depressed.’ But I want to encourage you to recognize the enormity of your current crisis, which actually transcends your stated desire to return to a contented state. Marrying someone and moving away from your friends, family, and the place you love: this is the kind of unsettling shift that makes you question your whole existence. While I do think you need to get out the door and meet new people, I want to encourage you not to retreat into distractions that you merely view as time-killers. Don’t seek out mere contentedness, counting down the hours until your wife gets home from the hospital. This is a rare chance for you to explore your relationship to yourself and the world.

You have to outperform right now, is the point. Not only do you have to make a big, awkward effort to get the ball rolling, and then make social plans even when you don’t feel like it, but you also have to go far beyond the bare minimum. You have to clean the apartment, sign up for a cheap personal trainer at the Y, order a good cookbook and teach yourself to make Indian food, go for a long walk even when the weather is terrible. Take on projects that will give your life a feeling of forward motion. Every bit of patience and hard work and enthusiasm you can conjure in the face of discouragement right now will pay off. This is about you reaching a new level of happiness, and cultivating a new kind of openness and acceptance and gratitude toward the world around you.

In a few years, you may end up somewhere else, but you’ll look back and feel proud of yourself. You’ll remember how you cooked baingan bhartha and painted the living room orange and took up Krav Maga and met some lifelong friends. You’ll remember how inexplicably happy you were in Sad City.


Spinning your wheels? Need someone pushy to whip you into shape? Write to Polly. Do it right now, motherfucker.

Previously: Ask Polly: I Feel Guilty About How Absurdly Rich I Am

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses. Photo by dichohecho.