I’m 31 and Single—Why It’s Hard and Great at the Same Time

written by HAILEY MILLER
Source: @bykwest
Source: @bykwest

When I was 23 and working at my first job, I made cookies for everyone in the office as a part of their holiday gift. I made seven different kinds of cookies for each of the 13 employees, and needless to say, the team was impressed with my mad baking—and I’d like to think time-management—skills. When I went up to the accounting office, I boldly made the proclamation that I was practicing to be an all-star mom—you know, the one who makes the best chocolate chip cookies and is super fun, so all the kids would want to come over and play.

Now don’t get me wrong, being a mom wasn’t my only goal or dream. There were career aspirations, health goals, and all of the other things that come along with being a type-A perfectionist, but the expectation was that all of those things would be accomplished with someone else by my side; with the loving feeling of a family.

Well, that was in 2011. Today, I’m certainly not baking cookies for all the kids. In fact, I’m not baking cookies for any kids.

When I look back at my childhood self, my high school self, my college self, and even my 5-years-ago self, I didn’t think I would be writing an article about being single—and I definitely didn’t think I’d be living in New York in a shared apartment with the very few things I own. Instead, I pictured myself married with kids, living in a home, being the most badass, cookie-baking mom on the block.

Whether that was a timeline I gave myself based on idealized expectations, memories of the past, or what I actually wanted, I’m not sure. I think we’re constantly evolving as people and coming into our own, and as that happens, what we thought we wanted (sometimes for the wrong reasons) versus what we actually want becomes a bit blurry.



Like many, I love the feeling of being in love. I love watching people falling in love. I love the sense of family that comes along with having that “person.”

But here I am 31, and I’ve never…

  • Taken a “date-date” to a wedding.
  • Been a “date-date” to a wedding.
  • Shared an apartment with a significant other
  • Had blowout fights that lead to passionate, loving make-ups
  • Had someone to share the details of my workday with
  • Been able to spontaneously grab after-work drinks with a guy that I’m not just getting to know from Bumble or Hinge
  • Had really difficult conversations and vulnerably opened myself up
  • Had my heart broken in my adult years
  • Compromised about life, like where to spend Thanksgiving and Christmas

And as you ladies in a relationship might be thinking “wow, what a dream,” the reality is that I’ve never done any of these things because not only am I single right now, but I’ve been single for the better part of the past eight years. Sure, I’ve had little flings here and there, but nothing that’s given me the full invested, committed relationship experience. You know, things like compromise and unconditional support.

During those eight years, I’ve watched friends fall in love, get married, have babies—and while I’m a big believer that you are where you’re supposed to be and that everything happens for a reason, I’ve started thinking more about my singledom. There are two sides to every story, right? The good and the bad.



I’ve read so many articles and books empowering single women to own it and why it’s actually amazing—that’s all well and good, but when you’re the single one, it’s not always so glam.

I can’t deny the ways that I’ve benefited from being single:

  • I’ve traveled somewhere awesome with almost every single one of my best friends (and solo!)
  • I engage in things I feel passionate about all the time
  • I’m independent and can hold my own; I love doing things alone
  • My friendships are many and run deep
  • I’d like to think I’m pretty self-aware 
  • I get to do what I want to do, when I want to do it
  • I’m living an amped-up version of “treat yourself”
  • I spend my time learning new things
  • I don’t fight over the remote

But at the end of the day, as humans, we’re hardwired to be intimately connected to other people. We’re supposed to find companions and fall in love. There have even been studies that show the healthiest people are those who are in relationships.  

So real talk: yeah, being single can be great, but let’s talk about why it’s really f*ing hard to be and how I’ve learned to manage emotions around because sometimes it makes me feel really sad.


Wondering “What’s Wrong With Me?”

This is probably the hardest part for me. I always think there’s something wrong with me. I’ve been on awful dates where the guy was rude or had expectations of me that I wasn’t ready for, and I left the date feeling like it was me.

I’ve also dated some really amazing guys—you know, the ones that got away. I constantly wonder “How did I let that happen?” Hindsight is 20/20.

Plus, that comment when you go home for Thanksgiving, “how are YOU single?” Doesn’t help. “Thanks, Jim, I’ve been asking myself that for the past eight years.”



I Feel Embarrassed

It sucks to always be the single one, and when people express their sympathy for me that I haven’t found “the one,” it sucks.


Dating Takes Energy

Dating can be really fun… until it’s not. Looking for “the one” at 31 is a commitment. It means online dating (not curling up in your bed every night) and a lot of bars. As much as I love going out and being social, I am a creature of comfort. I love taking care of someone and curling up at home, but that’s not really an option when you’re single and want a relationship.


It’s Confusing

I go out on a lot of great dates with awesome guys. I think a first date should be a pretty easy one—you’re just getting to know each other and have a lot to talk about. But where do you draw the line between emotional and physical chemistry? How much do you need at first? What should you expect when you’re online dating? It’s hard to decipher your feelings especially if you start to lose trust in your taste in men.


I-N-D-E-P-E-N-D-E-N-T (you know what that means?)

I have become fiercely independent. I have a hard time letting people help me or asking for help, and tend to take on too much. With this independence is the ability to do whatever I want, whenever I want—which is both a blessing and a curse. Learning to compromise is a skill, and sometimes I fear that I’ve lost this ability.




Self-Love Doesn’t Come Easily

Actually, self-love is really hard. Sometimes, you want someone to hug you at the end of the day and tell you it’s going to be OK. You want someone you love to tell you that those jeans make you look good and that you deserve the promotion more than anyone else. When you’re single, even when you have the best of friends, this security system and unconditional love doesn’t exist, so you have to work to build it yourself, and sometimes you just don’t love yourself.


You’re Not Your Friends’ Priority

I don’t mean this in a bad way, but it’s the truth.  Sure, you’re one of their priorities, but their husbands, their S.O., and their children are a higher priority. My friends are seriously the BEST at making friend time high on their to-do list, but it’s hard when they’re not available and you have to plan your weekend nights months in advance.



Loneliness is on the rise in America, which is ironic because we’re so digitally connected. There’s an inverse relationship between technology and in-person, human connection. Being single is really lonely and isolating at times, and for me, as I crave something that feels so far out of reach, it heightens the emotions of loneliness like it’s never going to happen.


You Become Guarded

Ever been ghosted? I have. I’ve been ghosted at every stage in the dating process, and I’m embarrassed to say that I’ve been a ghoster too. In the past two years, I made a commitment to be more open and honest with the people I’m dating—whether it’s one date or five. We’re human, and we deserve to be treated with respect.

It hurts to think someone might not reciprocate your feelings, only to never hear from them again (and it’s scary to think you might hurt someone else!). As time goes on, we naturally become a bit jaded by the dating scene, and it becomes even harder to get vulnerable, let loose and have fun, and get physically intimate.


So, single ladies: how do we deal with the hard emotions that come along with being single? When everyone says it will happen when you least expect it, how do we stop hoping our carts will bump into “the one” at our next trip to Whole Foods?

It’s not easy, and I’m certainly not there—we’re learning together. For me, it’s been a lot of self-reflection: reading books, forcing myself outside my comfort zone, and letting go of my expectations just a little bit. I know it might seem like a lot of work, but just like relationships are a lot of work, finding the right one can be too.

Since we’re setting a precedence of honesty, truth, and vulnerability here—yes, I want a relationship. I want the good and the bad, and I want the love, the fights, and the compromise. And guess what? Yeah, I still want to be the badass, cookie-baking mom.  

But there’s one last perk: I think I can now I can be an even better badass, cookie-baking mom and wife—because I know me, and I like me. I know that no relationship is perfect and no person is perfect, but I hope with time and reflection, the right person will come into my life.