questions to ask if you're still single
Illustration: Rachell Sumpter
1. Am I spending too much time with the people I love?
You adore your little brother the pediatrician—and his wife. So going up to Boston for the weekend to celebrate his birthday is a delight. The same goes for spending the following Sunday at your cousin’s first dinner party. And dancing the night away with your best female friend until 4 a.m. These people are fun, kind and affectionate...and always there for you.

Which is exactly why you might reconsider how much time you spend with them. Breaking out of a tight circle of friends and family in order to peruse the buffet at your niece’s confirmation and strike up a conversation with an attractive stranger about the pigs-in-a-blankets and the inherent appeal of even the tackiest ice sculpture is difficult. Hanging out with people you love is comforting. I understand this. In fact, I am the married woman who wants nothing more than to laugh my head off all night over by the chocolate fondue with my many stunning, intelligent single friends. But this is why I’m writing this article: because I want you to know all the things I’ve been thinking about for years—years I spent both with and without a partner. You must dump me. You must walk away from me and my marshmallow on a stick. Falling in love is a risk, one that for better or for worse, must be taken alone.

2. When it comes to the tough questions, why do I lack answers?
As any single person knows, close friends and family try to help you by asking you a lot of questions, like: Why are you so picky? What do you want? These inquiries may cause you to stay up at night, wondering why you are so picky or what you want exactly...because you don’t know why or what. You'll feel more and more unsure about yourself, and keep circling around these issues.

Here’s my thought: If you don’t know the answer to these kinds of questions, aren’t picky and you don’t need to know what you want. These subjects don't set off any fire alarms in your soul. They don’t apply to you. Throw them away.

Whereas, if a friend ask you: “Why do you always end up with the guy who disappoints?” and you suddenly want to punch her and hug her at the same time—because you’re so embarrassed, because it’s so true, because you’re too intimidated to approach the right guys, because your brother always called you horse face, because you still think of yourself as clumsy and awkward and wrong, even though junior high is long over and you’re successful and (other people say) attractive. Then you need to do some thinking. And then some rethinking.

The questions that help you build bridges to intimacy are the ones that you have one, two, or 47 screaming immediate answers to, answers that fill you with a flood of excruciating but valuable insight.

Next: "Do I have a love success pattern?"
3. Do I have a love success pattern?
The greatest thing about love, I believe, is that it’s the most democratic of human experiences. Anybody can do it, and just about everybody does it (with the exception of sociopaths). What some of us forget to value or recognize is that even if we aren’t doing it in a romantic way, we’re doing it in other ways—and doing it well.

Look at the people you love and who love you back. Now take out the family members, because you didn’t choose them. This leaves your friends. Narrow these down to the three you have the strongest relationship with, the ones who you trust in any situation. At first glance they may seem dissimilar. For example, one may be a quiet stay-at-home mom, another an outspoken interior designer, still another a wisecracking novelist. But your relationships with these three will have a few things in common, even if at first glance these qualities aren’t obvious. Going back to the pals above—which, okay, are my pals—I have to point out that all three are wildly independent people who are also pee- your-pants funny. And...not the best dressers.

This is where I do love well, and luckily after years and years of badly managed romance interactions, I met my husband, who shares all these same traits. Understanding that not only are you—like everybody else—absolutely, positively capable of love, but also that you are awesome at it with certain, very specific people gives you confidence, yes. But it also really narrows down the field. After all, how many funny, independent guys wearing plaid winter pants and a striped summer jacket can you find at any one rooftop cocktail party?

4. How do I look when I’m sitting alone—but interested in sitting with somebody else?
Perhaps you’ve gotten this advice: Go to a restaurant alone and eat dinner. Or: Go to a movie alone. The rationale behind these directives is that men who are at these venues and are also alone will see you, feel comfortable and come over to say hello. It may even be that I was the one who gave it to you.

But here’s the catch. I was a travel writer for many years. I strode into hotels from France to the North Pole, plopped down at the bar, ordered a glass of oaky-yet-overpriced Chardonnay and met...exactly no one.

My friend Sukie, on the other hand, can go to bar and meet someone in about 10 minutes. This is not because she is prettier, funnier or sexier than I am. It’s because of the expression on her face. She looks relaxed. She looks open, if not ready to laugh at the world’s dumbest joke. I look like I have a lot of stuff to do, stuff that requires me to choke back that wine and get right back to business in five minutes. It’s a facial expression I picked up to keep luridly friendly strangers on the street from striking up conversations about, say, my derriere.

The truth is that for much of our lives as women (and girls) we’re told to not talk to strangers, on the street or anywhere else. Even decades later, this training is hard to undo. You don’t have to give the men around you bedroom eyes, fling your hair around and pout your lips. Then again, you also don’t have to look stressed, exhausted, closed and annoyed. You can take a minute—think of the time your brother mistook your glue stick for Chapstick—and smile, genuinely.

Next: "What do I never have to do again?"
5. What do I never have to do again?
There are some perks to being a grownup. You don’t have to do everything for love...or even just for dating. You don’t have to go to lunch if you can’t stand long, lingering meals in the middle of the day that take you away from your hugely demanding, fast-paced job. You don’t have to go on blind dates with men who send you an email to arrange the time and date addressed to Kimmy when your name is Carol. You don’t have to go to yet another Oscar-night party at your sister’s house, where you and one guy are the only single people there and subject to all the other couples’ suggestions that the two of you set up the cheese platter the kitchen...alone.

To meet somebody, you may have to do some stuff you don’t want to. But you don’t have to do those one or two things (note: one or two) things you loathe. You don’t have to feel guilty or defensive about not doing them, either. Taking part in dinners and activities you do like makes it, well, all the more likely that you’ll have a good time in your pursuit of romance—and nothing is more attractive than happiness.

6. What heartbreaks have I saved myself from?
As time goes on, it gets tempting to just settle down with the guy who’d make a good father. Or the guy who will never leave you. Or the guy who all your friends like. Or the loyal, wise adorable guy with the big, fat heroin habit. Should you decide to go this route, it’s true that you won’t eat dinner alone. But being in a relationship with somebody you don’t love is like dipping your loneliness in chocolate. Once you get past the candy coating, it’s still there, only magnified, because you’re going to sleep next to somebody who doesn’t know the real you, because you can’t ever show him, because you can’t ever love him, which is the loneliest feeling in the world.

You may console yourself every day that at least you’ve got kids or the joint account. But you may also get divorced. Or you may go on, despair turning into seething silent rage and depression.

My point is: When every clumsy friend or family member offers help in the form of wildly misguided criticism (e.g., you have impossible standards, you don't really want to be in a relationship, blah, blah, bleck), please try to take a minute and congratulate yourself for not willingly being the cause of your own unhappiness. You have insisted and trusted in your own ability to find your own damn joy, to live a life based on the things you want, and you may just get it one day—due to your refusal of those you don’t.

More Life Lessons from Leigh Newman


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