Want To Make New Friends? Just Ask People Out

Sometimes when I’m spacing out in the shower, I play a game about infomercials. My game is to think about what product I’d evangelize about on TV (or these days, maybe on Instagram) with so much enthusiasm that I’d convince someone else to buy it. There is a moisturizer I got in a French pharmacy that I swear is exactly like La Mer for a fraction of the price. Or the cheap-but-sexy underwear I like to buy in bulk. But none of that is it. What I really want to sell to the world isn’t a product but an idea — or maybe it’s an action — that changed my life. Learn how to ask people out. That’s all it is. Do it and it will change the way you make relationships and cure you of your fear of rejection.

I don’t even mean it in a romantic sense. If I meet someone and I feel a platonic spark, I will take the initiative to ask them to get lunch or a drink or dinner. I have exchanged pictures of Gwyneth Paltrow wearing Gucci with an internet friend in Chicago and asked if she wanted to go to a play with me next time she was in New York, where I live. Once, I asked a woman I only knew as a friend of a friend to get drinks with me; now, we’re about to go on vacation together.

These are the success stories. I’m not mentioning the fellow writer whose essays I loved but had a stilted dim sum brunch with where we never found our friendship rhythm. I am definitely not mentioning the cool artsy couple who live down the street from me that I see all the time while walking our dogs. We exchanged phone numbers, and I asked them out to drinks at a cozy wine bar, and they never responded. (Maybe they think I’m trying to get them to become a throuple? Perhaps coffee would have been a better suggestion, on second thought.)

I’ve made my own mistakes in scouting potential friends. One barista I always chatted with turned out to be fun but put too much pressure on our very new relationship. She was the kind of friend who wanted to text me about drama all day long as if I was her unpaid therapist. I like her, but I’m not making any plans with her anytime soon.

But imperfection and even rejection is kind of the point of this exercise. The reason it’s so hard to make our feelings known is that fear that they won’t be returned. No matter how many times I may be advised not to take rejection personally, it’s hard not to. Especially when it’s relationships and not, like, a job interview or an apartment I want to rent.

How much am I missing out on because of my fear of rejection? Who am I missing out on?

Rejection can be easily avoided by not, to use a phrase my mother is very fond of, “putting myself out there.” But how much am I missing out on because of my fear of rejection? Who am I missing out on? When I started to break down my fear and really think it through, I realized how neurotic it sounded. Say I would ask someone from work if they wanted to grab a drink one sunny Friday and she said no. I’d… what? Feel disappointed? I would hurt for a few hours and feel some embarrassment for a few days and then I’d get over it. The stakes were not huge.

Which is why it’s easy to start small. Think of it in increments. My workout of choice, for example, is yoga, and I go several times a week to a studio in my neighborhood. Many of my fellow die-hards go at the same time most weekday mornings and have a friendly rapport, chatting about the weather or how hard doing three wheel poses in a row was. One woman and I were walking the same direction to a smoothie place (and yes, I am aware I am a yoga-and-smoothie cliché of a woman at this point in my life). I suggested we drink ours together in the park. A few smoothie dates later, and we went to dinner in the neighborhood and gossiped about celebrities and the perils of dating during a pandemic. It was a slow build to what is now a real friendship.

I like to think of asking people out as a muscle that needs training to become strong. I started doing it during the first summer of the pandemic, when many of my close friends were suddenly scattered living around the country; I was single, and I couldn’t bear the thought of interacting with anyone online anymore. So by the time I moved to a new neighborhood a year ago, I was confident in my skills. I met so many new people in my day-to-day life that suggesting I go get a drink with someone became so easy and breezy that rejection didn’t even scare me. I felt magnetic and charismatic. Maybe I was becoming that way, too.

I am well aware that the main association with asking people out is romance. And yes, I did that, too. The prospect of asking guys out was terrifying, but the purgatory of dating apps somehow felt worse. Scrolling bad selfies and worse jokes on the apps felt like mandatory homework at best, punishing myself at worst. I logged out and took them off my phone. I gave myself permission that I didn’t have to use them. But I had gone about two years without a date, and I really wanted to try to meet someone, somehow. So if it wasn’t going to be apps, it was going to be in person.

Last summer, I started going for it. The weather was hot, I was wearing a lot of little dresses, and I was determined to normalize not just asking out potential friends but potential boyfriends. So if a friendly man in pants splattered with paint lingered while petting my dog every morning, I’d suggest going to a movie. If a friend of a friend of a friend slid into my DMs to congratulate me on a story I wrote, I’d give him my number and say we should grab a drink sometime soon. If I talked to a man for a solid five minutes about the art of grilling at a birthday party in the park, I’d tell him to take me to his favorite spot for barbecue.

I was brazen, which doesn’t necessarily mean I was a dating superstar. One guy politely told me he had a girlfriend. Another one told me he had a girlfriend at midnight, after three martinis and a super sloppy kiss. (I told him, less politely, to leave.) There were degrees of success, just like anything. I told a flirtatious guy who sold me a painting to come see it hanging in my apartment. We shared a cheese plate and a few make-out sessions but nothing serious.

But like making new friends, asking guys out got easier and less scary. If the guy who petted my dog and lingered never did return my text about dinner, I felt mildly weird when I saw him around the neighborhood, but it ultimately didn’t bother me that much. On to the next one. I saw myself as someone who went on a decent amount of dates and the stakes for all of them felt pretty low.

I now had a lot of people in my life. With all my newly amassed platonic friends, I threw a big (pre-omicron) holiday party and watched in delight as I introduced two people who grew up near each other or two others who had both rowed in college. Friendships were being made all around me.

It was at that party that some old friends brought a new friend of theirs. We talked for all of three minutes, but I told a mutual friend I thought their new friend was cute and to give me his number. I texted him, and we made plans to go out for Chinese food. That was the last guy I’ve asked out in a few months. We’ve been dating ever since.