When it comes to talking about dating, singledom is basically only ever framed in one way: It sucks. There are countless columns, blogs, and articles dedicated to helping single women hack the system, deal with unsavory suitors, and combat the stigmas and stereotyping that the coupled world rains down. Positivity comes in the form of "happy ending" stories; in every article we read about a lonely person learning something from the dating scene, a match of some kind presents itself at the end. "If you follow this advice," the stories seem to say, "you won't have to end up single, either!"
And yet, today, 50% of people in the United States are single, and it's silly to think that all of them feel cynicism about not being in a relationship. If we've learned anything a lifetime of conversations spurred by The Rules, it's that there are no rules when it comes to seeking out love.
So, in an effort to transcend that conversation, we turned to six single women who take wildly different approaches to dating - and life. And, while their experiences, outlooks, and tastes are very diverse, there are a few universal trends (and common misconceptions) that prove exactly how multifaceted the world of singledom really is..
Online Dating Is Ubiquitous....But Imperfect
The single person who hasn't yet tried online dating is becoming increasingly hard to find. With thousands of different platforms catering to millions of preferences, orientations, and levels of effort, online dating services are heralded as the grand timesaver. Online, you're able to shop for a date like you'd pick out what you want delivered for lunch - with all the information laid out, you get to connect and engage on your time (without having to spend money on a drink tab...until you're ready).
Says Pippa Lord, founder of lifestyle site Sous Style, "What I like about online dating is that it sets up the relationship from the beginning. It's like we're both just trying each other on to see if we're romantically connected." Shani Silver, director of community at Keep, agrees that for busy women like herself who prefer to have a lot of options, online is the way to go: "The whole premise of online dating offers so many more options that you don't have in real life. When you're out, there are just very limited options. Everybody's coupled up or nobody's saying hello. It's very difficult to meet people by just going out."
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However, that doesn't mean there aren't pitfalls - and big ones at that. For Pippa, finding a connection online just doesn't compare to finding it in real life. She considers herself a pro at "bumping into" dates on the street (more on her technique later) and values those quality interactions. "I think online, there is this next, swipe left, swipe left, swipe left culture that can be toxic, whereas if you actually meet someone on the street or get introduced by friends, there's this authenticity to it that can't be replicated. Corporate lawyer Sonia agrees and actually believes that online dating is more work than it's worth, especially considering her packed workweek: "It's not convenient. I won't go out with guys on the weekends because it comes with a lot of uncomfortable implications, which means that I'm going on dates Monday through Thursday, which means I have to leave work early. And then, if the guy sucks, all I'm thinking about is that I have so much work to do, and I haven't done it. It's really annoying to spend one of your only free evenings doing something you don't want to do. Plus, it's a weird concept that I could go on a date with someone who I wasn't attracted to - because how do you really know if you vibe with someone, if you haven't met face-to-face?"
So, Where Do You Get What You Need?
For Sonia, whose lifestyle is a bit too busy for the modern conveniences of online dating, her solution might seem a bit counterintuitive: matchmaking. Thought it might sound old-school to some, she turned to an exclusive, NYC matchmaking service that immediately set her up with a stranger. The result? "He was great. He definitely had everything I was looking for. He was a gentleman. And, that's the thing with the matchmaking service - they really vet who gets into their pool, and they're very particular about who they take on. We didn't have that instant chemistry, but I had a good enough time with him that we went on many more dates, and then I found myself developing an attraction to him. That was a really refreshing experience." It didn't work out between the two of them, but Sonia's matchmaking experience was positive enough that she's willing to try the service out again.
The vetting process is something that Shani also feels is missing online. After moving to NYC last year, she's noticed that there's a prevalence of bold-faced lying that happens on profiles - something that would be eradicated with a human third party. "People say that they live in New York when they really don't. I went out with a guy who made absolutely no mention of the fact that he was just in New York on a business trip. That's happened twice. Also, height is one of the things men lie about the most. I actually set my height requirement to 5'11" because 5'10" is the most common height that guys lie about. Last summer, I went out with four guys in a row who all said they were 5'10", and all of them were shorter than me, and I'm 5'6". I don't mind dating someone who's short, but I do mind dating someone who lies. I don't really understand the rationale behind lying when I will eventualy meet you and see you. "
Clearly, it's not for everyone. Recently single, Alex stays far away from online dating, but also doesn't have a hard time finding women to date in real life. "I have always been more attracted to friends of friends or interesting in meeting people at birthday parties, which always seems to be the way. Seriously - if you get invited to a birthday party, go! That's where I pick up all the ladies. I tried OkCupid for like two weeks and I would get these crazy messages from people, and good for them to actually be going after what you want, but jeez. I'm not going to go out with you when you're weird to me.".
There's A Lot Of Talk Of Intimidation
The word "intimidation" gets bandied about a lot when it comes to talking about failed dates. On the one hand, it can be a crutch people use to explain a lack of interest from the other party, and the use of the word has become so pervasive that the mere mention of the "intimidating woman" can elicit eye rolls. For many women, having a great job, a high salary, good looks, and a sharp wit are assets - and to assume that those things aren't what other men (or women) want is to shortchange ourselves and them. Says Pippa, "The whole intimidation thing is less about what you are, and more about not being able to make a man feel like a man. Don't get me wrong, it's not about dumbing yourself down, but it's about approaching things with a sense of vulnerability while having an 'I am who I am' attitude. Because, let's face it: What's more vulnerable than hoping that someone likes you as much as you like them?"
Conversely, Shani sees intimidation as a good thing. "I've been told that I'm intimidating since I was 21 years old - by men, women, family members, friends, coworkers, everyone. I have no idea what's so terrifying about me, but I actually don't mind it. I consider it sort of good in that, if I intimidate you, I shouldn't be dating you in the first place. The people that I have dated and have had great relationships with haven't found me intimidating at all. I think it definitely precludes a lot of guys from dating me, but that's good." Sort of a built-in filtering process..
...Especially Around Careers & Money
However, there are certain factors that make certain women seem less dateable than others. Priti is a med-school student who frequently feels like her appearance and job cause men to shy away. "I'm six-feet tall. I'm in med school. I consider myself pretty smart, and I'm vocal about it, and that seems to turn people off. I know girls in my class who have the same problems as me and were talking about whether they should lie on dates and just pretend that they were nurses. It's terrible because it presumes that nurses are less smart or essential. It also sucks that that's how successful women feel forced to think."
For Sonia, being attracted to ambitious, successful men has led her to mainly date men who work in similarly high-powered, high-salaried jobs like finance or law, where money is a very important factor. "Men feel threatened by the possibility that I might have a higher salary than they do, because the sad fact of the matter is that when you're in a traditionally high-powered career, like law or finance, you can't help but measure your worth by your salary. [In my industry], salaries are so transparent, and you can always ballpark how much someone makes based on their title and where they work. Generally, I won't go out with guys who make less than me. I don't want to deal with any insecurity. I would consider dating someone who made less than me if I felt that they were totally secure with themselves, but I haven't ever found that to be the case. It's the money, and it's also that alpha guys have that instinct that they want their woman to raise their kids. And, when they see a corporate lawyer, they don't see a woman who has the time to do that. I find myself becoming defensive about things early on the date, and finding a way to mention that I want to have kids on the first date, so that he doesn't assume I'm someone I'm not.".
Breakups, Lies, & Double Standards
Especially for those who've been dating for a while, the whole premise of dating for the purpose of finding a partner often feels like a series of rejections (whether it's from you or the other person). And, that can get tiring, fast. For Shani, it's all about the ratio. "To [get] ready for dates, go on them, and then come home from them…when that whole cycle of everything it takes to meet someone constantly ends up in disappointment, that makes me feel like an insane person. A definition of insanity is doing the same thing over and over again and expecting different results, but when it comes to dating, you always expect different results."
However, Alex has turned her fear of rejection into a strategy. "You share yourself so deeply with someone and then it ends. My friend says that when it comes to breakups, you just need to choose who you're willing to hurt for. Learning to differentiate between who's important and who isn't. So, when I started really dating, I was in it strictly for the pleasure, and the flings, and pursuing, pursuing, pursuing like crazy. Sometimes people call me a heartbreaker. But, I think the reason that I've become so aggressive is that it puts the ball in my court. I control it because the thought of being rejected, and pushed away, and having my feelings hurt is so horrible."
Whether your relationship lasts a couple weeks or a couple months, it can still be disorienting when it ends. "Breakups mess with your head," Sonia says. "There's just no guarantee when a guy will flip a switch. To everyone else, including yourself, things could be going really well, and then you just get blindsided. In urban places, people can get so distracted by options that I think that nice guys are still looking for something that I don't even think is real. They think they're going to get everything they want, and that keeps them from developing real connections. The thing is, for guys, it's not an issue. When they get to be older, they can still find a young girl to date. It's absolutely not the same case for girls."
For Pippa, who considers herself exceptionally open to all sorts of people, the stories of failed dates reach nearly epic proportions. "I met this guy a week ago crossing the street in the blizzard, and we exchanged numbers. And, after we went for drinks, I Facebook stalked him, as people are wont to do. And…there's a picture of him holding a woman with a pregnant belly posted just a week before our date! So, I texted him saying, 'Hey, saw you on Facebook, congrats on the baby.' Yikes. So, that's been coming up quite a bit.".
And Of Course, All The Pressure
Whether it's internal, societal, or coming from your coupled-up friends, being made to feel like "a single person" can be a frustrating part of singledom. "People say to me, 'I can't believe you're still single,'" recounts Shani. "What bothers me is the word 'still.' It's just what I am; it's as significant and insignificant as any other part of my life. If I meet someone, it won't be: 'I'm finally not single.' It's just another part of my life that'll change. There's a lot less tolerance for women being single as they get older. There's the assumption that there's something wrong with it. But then again, after seeing so many happy people everywhere, and knowing that everyone you know is matching up and getting married and having children, and having second children…I think that the only pressure that exists is what I put on myself. It's really a product of seeing stuff coming easily to other people when it doesn't come to you. That's the big bummer."
Priti, too, feels like most of the pressure is coming from herself. "I worry about whether there would be a point where I could commit to being with someone and meet the needs to be in a relationship. And, I worry that a person's not going to come along who I feel like I want to do that for. And then what? Do you settle for someone? Or, do you hold out and keep waiting? The worst is when I hear people say, 'Don't worry, it'll happen.' Firstly, that's not advice. And, second, it's not based on any facts. It's an emotional blanket. I don't mind receiving advice from people, especially my friends, because even if I don't agree with it, it's important to hear all those different perspectives. But, what am I supposed to do with 'Don't worry, it'll happen'? How do you know?"
For Sonia, whose career hinges on the professional climb upward, feeling inter-office pressures to climb socially is also part of the job. "I think that a lot of corporate women in New York are just looking for a NYT wedding announcement. If you look up the people at my firm who are married, they all have a wedding announcement. Those are the people I'm surrounded by. It's not them putting direct pressure on me, but they're presenting this social ladder that you need to have a partner to climb. You want that person that you can bring to your company holiday party. It seems really weird and crazy, but in a way, you end up wanting those things because you see how it benefits other people at work.".
But, Dating Teaches You A Lot About Yourself
When you're constantly finding yourself in situations where you need to present some version of your best self (or as Pippa says, "your representative"), there's a lot of self-reflection, growth, and fun to be had in trying things on for size. For Priti, who's dated consistently but has never been in a long-term relationship, "it's a great way for me to figure out how to become comfortable with myself. At the end of the date, it's just myself and another person, and it's up to me how I present myself, and the way that I choose to change the course of a date. Dating forces you to be self-reflective about the way you want to be seen, and that's powerful."
Similarly, Erica, who recently ended a long-term relationship that comprised the majority of her adult life, and found herself single for the first time since high school, sees dating as a growth opportunity. For her, dating is as much about meeting new people as it is about meeting this side of her: "I'm dating because I just want to learn what I like and what I want. I think I've discovered that I'm the kind of person that wants to love things about people. I'm just trying to figure out if there is a set of qualities that I definitely want in someone. I was never the kind of person who was happy because I'm with someone, but rather I'm happy because I'm with this one person. It's not about singledom vs. coupledom for my happiness."
Plus, for her, being on her own has been a mixed blessing on a larger scale. "I realized that I'm totally responsible for my own happiness," she says. "I had to figure out how to be happy in the absence of this one person that I used to spend all of that time with. That was a really useful thing for me to learn. I spent all of that extra time reconnecting with old friends or making new friends or doing more of things I've always loved to do…like, for instance, dancing. If you have a boyfriend and go out on the weekends, by like 1 a.m. you're like 'Let's go home, baby.' But, when you're single, you don't have anyone to go home to, so you're like 'f**k it, we're going to stay out until 5 a.m., and I love that.".
And, It Can Be Pretty Damn Fun
For Pippa, dating in and of itself is fun - and she chalks it up to her openness. "I'm a very single girl. I've always been single, but I'm very lucky because I meet a lot of guys and have a great time. I meet them on the street, on the train, everywhere. I think it's because I smile at men. Because at the end of the day, who doesn't want to be smiled at? And, boys get so excited, it's hilarious. And, when the girl that's smiling is actually nice and curious and interested, a smile gives a guy a green light. If he's available, he'll make a move. If not, you know you made someone feel hot and keep on walking. There's no bad outcome. It's such a good time."
Alex agrees that the wide range of available options can be thrilling: "For five years, while I was in a relationship, I didn't have a wandering eye. And now it's like, holy shit, finally. There are so many people in this city. I'm free to be me and explore different kinds of people and date outside of my comfort zone, and that's incredibly fun. I have been sowing my wild oats."
Beyond the joy of flirting and romance, having the time, emotional availability, and motivation to build deep, long-lasting friendships - both female and male - were also a common advantage touted by the women we interviewed. Said Erica, "I always knew I had good friends but my ex was who I depended on the most for emotional support. But, [since my breakup] I've realized you can depend on a lot of other people. Now, my love and support isn't so concentrated with one person but spread around."
"Being single in New York is incredibly hard, but also incredibly easy," says Sonia. "You will always have single girlfriends in the city. Most of my female friends are very single and they're beautiful, smart, and hilarious, which is great company. You go to a nice restaurant on a Friday night, and you're more likely to see a group of hot girls together than a couple. When I've been in relationships, I've almost felt left out when my single friends are doing single-friend things."