Jacqueline Speaks: “I’m Single in My Mid-Thirties. Am I Becoming a Cliche?”

Let me get some disclaimers out of the way here.

I have a very good life. I live comfortably in the city I love. I have a job that’s challenging and fulfilling. I call some of the best people in the world my friends. I have a supportive family. I’ve been loved by some very, very good men. I am living a life I cherish.

It’s also a life that I have chosen. I don’t own property. I’m not married, and I don’t have children. I rent an apartment in a non-trendy neighborhood with a woman who’s one of my favorite people and closest friends. I work from home. Simple things — being warm, taking a bath, drinking bubbly white wine, walking my dog, laughing with a friend, an incredible meal — make me truly happy.

Yet I’ve been angry, recently. And sad. Yes… I’m sad.  I’m lonely. And I’m not quite sure how I got here.

On our show, Ben has sometimes said, “there’s a reason why single people are single.” My ears first took that as, “if you’re single, there’s something wrong with you.” But I know Ben enough to understand that he’s not just saying that. A reason could be because of baggage, distrust, because someone’s narcissistic or cruel or selfish, yes. But I like to think single people are single because life things happened in an order that somehow brought them to where they are.

And so I turned that idea to myself. Why am I single?

Well, there are a number of reasons.

I dated a man for almost ten years; we broke up when I was twenty-eight. While our friends were in and out of relationships, we had each other. Even though we never seriously contemplated marriage we were happy together, until we realized that we weren’t happy enough. I don’t regret a single minute with him, but we both missed out on many years of dating and discovery. He’s now engaged to a wonderful woman and they have a beautiful child together, and I’m 100% happy for them. He has the life that he wants, chooses and loves, and I have mine. But that brings me to another “why I’m single.”

The boyfriend after him wanted children. He promised that if I stayed with him (in Kentucky) he’d make me happy for the rest of our lives, and I believe him. He is kind, supportive, and talented. He treated me well. But I don’t want the picket fence and babies at my feet (I fully support those who have/want them, but that’s not me, as I wrote for Cosmopolitan and Elle). At the core, we wanted different things; he wanted a family in the suburbs, I wanted my creative life back in New York. Now we both have them.

The man after him broke my heart. My whole being told me I’d spend forever with him, and he’d told me the same before I’d even uttered those thoughts aloud. He wanted a family, and for him I said that I would make us one. Then, as young and crazy love sometimes does, things quickly shifted: he left me, and I fell into a darkness I didn’t know could exist for me – the independent, happy, spiritual, everything-happens-for-a-reason me.

There are men between and around these three. Some I dated for weeks, some for months, some for one night. Some were for love, some for friendship, and some purely about lust. There were also waves of my illness, my heartbroken depression, and my revival. There was a deepening of who I am, a newfound confidence, a sense of peace and a renewed love for the life I choose to have. I’m in a good place right now: not the healthiest I’ve ever been, but not nearly the sickest; not the most guarded, but not rashly uninhibited; not naively open-eyed, but not distrusting; neither frantically happy nor frequently sad.

Yet I am here, alone.

I am often alone because my body needs me to be, as I wrote for Cosmopolitan. And I enjoy it for the most part; an extreme extrovert for most of my life, I’ve naturally become more introverted as I’ve aged, and I have a huge appreciation for quiet, solo restoration and reflection.


Being lonely is different.

Dating now is far different than it has been in the past. I used to not have to think about dating: whether someone would find me in real life or online, it was easy to date, to dine, to have sex, to find someone who wanted me. I honestly don’t remember if I did anything in particular to attract such attention; I was just being honest about myself in whatever moment I was in.

Now, I’m equally as honest. Despite the melancholic through line of this story, I’m happy. I’m fun. So how did I get here?

I’ve been cranky this week. I’ve found myself lying in bed resting or going to a function or sitting at a table and thinking, “I wish there was someone with me to care about.”

I don’t “need a man” to fulfill me; my life is extremely fulfilling. I don’t believe that everyone needs a partner. For much of these past few years I’ve really enjoyed being single, as we discussed on our 9th episode with Lisa Mendelson. But I’m not naturally a lone wolf. I’m a caregiver. I like to give to others. I’m happiest when I’m baking something for a friend, or cooking for an intimate dinner party, or dropping off chicken soup or “magic cookies” to someone under the weather. I have a lot of love to give, and there’s a lot of love I’m open to receiving.

The headache is, this makes me feel like a cliché; a woman whining about how she’s got her shit together yet can’t find a man. My closest girlfriends – single and dating and struggling while I was comfortably paired off – are now moving in with boyfriends, or getting married, or having babies, or moving out of the city for larger spaces. And I’m still here: owning who I am and what I want, practicing compassion for myself and others, generally having my shit together, and getting stood up on the day of a date from another lazy guy I met online.

I don’t know how to change this. I don’t know how to cycle myself out of this week and back to where I was a few weeks ago; happy and confident and owning the fact that I have a full life on my own, as I shared on one of our shows. Where going to events solo is more fulfilling than going with another boring date. Where spending my energy on the people I love makes me happier than swiping left or right.

I want to say I defy the cliché. The cliché that’s included so many women I admire. That’s spanned from Mary Louise Parker to Gloria Steinem to the Carrie Bradshaw quartet to the thousand of faces I see on a daily basis and to the many wonderful women in my life ruling the world.

On Monday we’re going to talk about the frustrations of being single in your thirties. We’ve spoken a lot about what works right and what doesn’t on pretty deep levels, but as of now Monday’s for bitching. Bitching about being ghosted, about superficiality, about the finances of dating, about disappointment.

And maybe after that I’ll be cleansed, and can get back to being a happy, ass-kicking single lady again.

3 Comments Add yours

  1. A. Sanborn says:

    Being lonely isn’t a cliche. It’s human. I think the cliche is the societal push to attribute feeling lonely solely to being single in your 30s. Trust me, us married folk get lonely too. Even when we are sitting right next to each other on the couch…especially then, ironically. I wouldn’t worry too much about why you are on the path you are on. Looking back and analyzing can certainly help shape our future selves and make important improvements – but don’t stay there too long. You are indeed a kick ass single lady. Be grumpy and lonely! Let it happen, indulge yourself for a bit. You, yourself, are no cliche, friend. Have faith in that! Miss you.


    1. I adore you. And miss you, too, horribly. Think of you a lot. Thank you. xoxox


  2. Dorota says:

    It seems to me that the cliche and the spinsterhood stigma stem from the (erroneous) idea that every coupled person has chosen to be coupled and every single person would love to be with someone but no one wants them. In other words it is all related to the ful awful “desirability” value we often attribute to people. Or market goods. I think it takes courage to be alone. And to admit to feeling lonely. Thank you for your honesty.


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