How to Know If You’re Settling

There are plenty of labels assigned to chronically single women, but there’s one in particular that’s dipped in blame with just a touch of accusation. I’ve heard the word for most of my adult life, even dating back to my teen years.


I was often labeled “picky” by a myriad of men who saw my single status as a sign that I was doing something wrong, occasionally by friends who were paired off and wanted me to be, sometimes by family members who knew nothing of my dating history. “Well, you must be picky.”

I never liked being called “picky.” It seemed petty. The word made me feel like I was some dreamy young girl with her head in the stars. It made me contemplate questions like, “Am I being too hard on men?” or “Is what I want unrealistic?”

See, entertaining the word “picky” is the gateway drug to settling.

Most of us have had at least one spark-filled relationship with an emotionally unavailable partner who didn’t really want to commit. The kind that left us thinking, Okay. Not fun. Let’s try something different…

And so we do. And for every one-date wonder, there’s a person we go on multiple dates with despite a conspicuous absence of something, chemistry, connection — that thing that makes us excited to put down our book or face inclement weather just to see someone. We think, Maybe. We hope.

I used to wonder the longest a person ever waited for an emotional blip to magically materialize with their soulmate. My personal cut-off was five dates with the great-on-paper guy, all of which felt just a little bit empty and made me happy to return home alone.

The truth of the matter is no one tells you what it looks like to settle.

I’ve seen a lot of women internalize the idea that they are “picky” and decide to try being a little bit lonely within a relationship. One friend, over coffee, 10 months in with her girlfriend, said she felt “destined” for that distinct form of emptiness. Another such friend called me many months into her relationship, crying on the way home from a canoe trip because she felt so “disconnected” from her boyfriend (they are still together).

Yet another friend said her current relationship felt sort of like being caged, but at least it was better than her last one. “That was like being in chains. It’s better by comparison.” Eventually, she copped to the problem: “I can’t help but feel I’m missing out on something else out there.” This couple is also still together.

The truth of the matter is no one tells you what it looks like to settle. Maybe that’s because most people feel unsure about what it looks like. A recent study published in the journal Social Psychological and Personality Science revealed that those considering a breakup typically had firm reasons for leaving and for staying. This leads to an I-don’t-know-maybe-I-should-but-then-again-maybe-I-shouldn’t sort of ambivalence where something tells you that you should probably end it, but then again, it’s pretty…okay. You think you might be settling, but also, what if this is all there is? What if this is “good enough”?

I sat across the table from a friend years ago as she contemplated the question of settling with a sparkly diamond lodged between middle and pinky finger. As soon as the waiter left us alone, she asked me, “What do you think it means to settle? I mean, what is it, actually?” It was the first time anyone had asked me point blank. Her fiancé was one of the great-on-paper types, but I could see her angst grow the closer the big day got. This query felt like a massive philosophical conundrum akin to the meaning to life.

My answer to her was gut-level. It is still my answer to anyone who asks me today. “It’s settling if you feel like it is.”

The definition of settling can’t possibly be universal; settling is individually felt, a gut-check against every measure of connection we’ve experienced and imagine to exist. I know I’ve grown up on enough Disney fairy tales and rom-coms to feel unsure if my expectations are skewed. To end it with that guy who makes me feel just a little bit empty, I have to believe that what I’m looking for is out there, even though I’ve yet to encounter it — or, at the very least, seen it stabilize into a lasting relationship.

But our generation just wasn’t designed to settle on connection. We’re idealistic, emotionally intelligent. More women are more financially independent and self-supporting than ever before, surging past our male counterparts. We’ve embraced assortative mating with our equals, both professionally and in education, meaning relationships are purely by choice and for love — a very new phenomenon in the entire scheme of history.

With increasing “options” in the dating landscape, we’re also delaying marriage and kids in favor of playing life’s great field, frequently to gather data and solidify what we’re looking for. We explore different types in search of someone who feels like The One, at the right time, who wants the sort of partnership we want, supports our dreams and wants to merge lives.

Pheeew, that’s a lot. But we alternate between phases where we’re committed to the vision, and phases where we question our single status or if our ideals are unreasonable. Maybe someone calls us that oh-so triggering word “picky,” or implies it. You can often repeat the same dating cycles over and over again for years until you exhaust yourself out of the dating market.

I got over the pressure to find a relationship somewhere in the middle of writing my book last year. I think it was something I felt, long before I was actually able to articulate it, as I didn’t have time to date anyway. Despite being single for most of my life, it was the first time I truly and deeply sunk into that singleness and embraced it for what it was: Awesome. I related when Rashida Jones, in an interview for The Guardian, said: “I had the full princess fantasy: the white horse, the whole being saved from my life, which is ridiculous. What do I want to be saved from? My life’s great!” Ah. Yes. I could inspire myself.

You don’t owe anyone an explanation for ending a relationship or staying single.

So then, with dating, I was looking for something else. Not saving, but something greater than what I had alone. I realized that dating all the wrong men was a barrier to feeling inspired, and I can honestly say those inspired connections are very rare.

And what is connection, anyway? Another tricky word to define. It can be described a lot of ways: attachment, support, understanding, history. But the connection modern-day daters are looking for? I firmly believe it’s feeling the endless potential for growth with a single person. Per psychologist Arthur Aron’s self-expansion model, it’s someone who seems to help you become more, which might be harder to find than ever before.

Simply put, most modern women don’t “need” a relationship for opportunities, as they might have benefitted from one in the past. We are pursuing more, and slowly obtaining it. We are independent, financially and in spirit. We are the bosses of our own lives. Rather than shirk away from our single status, why not think of it as an achievement? We’ve earned it.

The next time someone insists you’re too picky, do what I do: Tell them you prefer “selective.” You have every right to be. You don’t owe anyone an explanation for ending a relationship or staying single.

But on a personal level, the next time you wonder if you’ve been too picky, ask yourself if you’ve (realistically) broken it off with any commitment-oriented prospects who inspired you. The next time you wonder if you’re settling, ask yourself if it feels like you are. The next time you wonder what connection really is, and if you’ve ever found it, ask yourself if you’ve felt that “click” with anyone who seemed to provide genuine opportunity for growth (together and apart).

I’m a big believer in feeling your romantic decisions deep in your core, no matter what they are, no matter who on the outside does/doesn’t understand. The law of not settling is “f*ck yes or no” to the bare-bones connection you feel with a potential partner. Anything less, and you either have more data to collect through dating so you don’t always wonder, or you haven’t found the great and magical “it” yet.

So, how do you know you’re not settling? You don’t feel like you are. The relationship in question might not always be easy, but the decision to pursue it should be.

Jenna Birch is author of The Love Gap (January 2018, Grand Central Life & Style). Click here to read her last post for Man Repeller, “What If This is the Reason Straight Dudes Won’t Commit?”

Illustrations by Katherine Moffett; follow her on Instagram @whensdessert.

Jenna Birch

Journalist, dating coach and author of The Love Gap.

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