Ask Polly: Am I Settling?

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Dear Polly,

I’m 27 and have been in a serious relationship with my boyfriend for four years. We’ve been through a lot. We’ve grown and changed together in a lot of healthy ways.

We’re very compatible in that we are very comfortable together. We like to do the same thing with a free day. We lift each other up when the other is down. We make each other laugh. We even have a lot of mutual weirdness/oddities. We rarely fight. We’re nice to each other. We’re attracted to each other. He makes me feel like ME. A hundred percent comfortable. All good things.

But I find myself bouncing back and forth between blissful happiness, sure that this is it for me, and stomachache-inducing stress that he isn’t what I want.

I’m a little more intellectually curious than he is, and more well-spoken. He jokes that I’m “the smart one.” I’m just a stronger personality. (Very douchebaggy thing to say, admittedly.) He has his areas, too. He’s not a doormat or a doornail. Or a plastic bag. He’s smart and witty, etc., and his tendency to not overthink plays to his benefit I’m sure. Sometimes I wonder, though, if he’s bringing enough to the table intellectually (for me). Like, can’t he overthink just some things? I’ve just always considered introspection a sign of intelligence (a hugely self-serving belief!). In times of doubt I find myself comparing him to other (usually older) guys who are better conversationalists and seem to have stronger worldviews. Guys who have deeply thoughtful advice.

Anyway, maybe I’m asking him to hit my every marker, and that’s unfair. Because we are just so … easy. We are easy. Really. Except when I make it hard every once in a while with my circular thoughts.

Also, he has essentially no serious doubts and has been sure I’m “it” since about week two. Dudes can be so sure of themselves. It baffles me!

I’m also two years older than him, which can feel big at our age. He’s immature in innocent ways; he just plain feels younger sometimes. Important to note that when I get out of my doubt-funk, a lot of these things disperse and don’t feel that true. I’m so fickle.

During my times of doubt I convince myself that my doubts are silly and that I do want this. I can’t decide if that’s wrong or not. I’m definitely scared of ending it, but I’ve been through breakups before. I know I would be okay.

I just can’t decide whether to trust the doubts or not. Because sometimes they feel like they are coming from the same shallow place that, say, reading about some fabulous person’s New York life and then getting sad about my pathetic little one comes from. Because in that sense I SHOULD think my way out of those holes. The grass-is-greener mentality DOES need to be battled, not trusted. There is a difference between genuinely wanting something else and forgetting yourself and wanting what seems glamorous/unrealistic.

The blissful happiness will return I’m sure, and those spells always last longer than my doubtful spells. Much longer. And feel really good. But the boomerang of fear is zapping all my energy, and feels unfair to him.

Am I settling?


Dear Unsure,

When I was younger and dating, I never knew which doubts to take seriously and which doubts to ignore. I had trouble letting them go, even when I wanted to. I would will myself to JUST STOP IT and accept the great thing I had, and they’d still come rising up out of the blue to pummel me.

Eventually, I started to believe that the doubts would always be there. So I got better at living with them — even when it seemed like they were ringing in my ears at night. I thought everyone had doubts all the time. I thought committing to someone was simply deciding not to pay any mind to the many, many doubts swimming through your head.

In my early 30s, I was dating this guy I’d committed to in spite of a vast sea of doubts swirling through my head, and I was assigned a piece about psychics for a women’s magazine. I sat down with a psychic and she looked at a photograph of my boyfriend and she asked me, “What are you doing with this guy?”

I burst into tears on the spot. That wasn’t the response of someone who was sure of her relationship. The psychic knew it. She said, “If you can’t defend your relationship in a court of law, then you shouldn’t be together.”

At the time, I thought her assessment was unnecessarily rigid. What did she know about how I felt about my boyfriend? What did she know about our life together? But over the years, I often find myself recalling her very cut-and-dry perspective: If you can’t quickly and clearly lay out WHY you should be with someone, why you’re the perfect team, why you feel grateful every day to have found that person, it’s probably a good idea to move on. Another way to look at it: If you had a daughter, and she were dating a guy like your boyfriend, would you tell her to stick with him? Or would you say, “You don’t feel emotionally and intellectually fulfilled with this guy. He’s not a conversationalist. He’s not a seeker. He’s content with whatever. This makes him very easy to love, but it makes your life feel small, and it makes you restless. You want more.”

I think that’s probably the truth of your situation, Unsure, as hard as it is to hear. Because even though it’s easy and comfortable and he loves you and he’s sure about you, even though those conditions are very relaxing and you will surely miss them when they’re gone, you want a partner who can understand the complex turns of your mind. This doesn’t mean that you’re smarter than your boyfriend. He’s just not attracted to the same complicated questions that you are. He doesn’t like turning over big ideas in his head in the hopes of breaking new ground or reaching some interesting epiphany. He doesn’t seek answers the way you do.

For me, there’s nothing more satisfying than trotting out some complicated, tangled, unwieldy thoughts and emotions and instead of just listening patiently, my husband throws ideas into the mix, offers his own insights, makes stupid jokes, and most of all welcomes the full brunt of what I’m bringing to the table. The difference between being with someone who’s engaged and eager to dive into complicated conversations and someone who’s not that into hashing things out? To me that’s the difference between feeling relaxed and happy and satisfied and feeling like an impatient shrew around the clock. I’ve settled for less plenty of times, but looking back, I don’t know what I was thinking. I was always the happiest with the complex thinkers, and I was always dissatisfied and depressed and lonely in the company of reductive thinkers who didn’t really love complex, rambling conversations.

Because for me, these kinds of conversations aren’t just the antidote for existential loneliness. They also make everyday interactions more satisfying and reassuring. You can trust a guy who understands you well. You know he has your back. You know you’re in the right place.

What’s tough about your current situation is that you are pretty comfortable in spite of these incompatibilities. Things are easy for you. You’re with someone who knows he wants to stick with you forever. I had a boyfriend like that once. He was also two years younger; he was also very sure about me. But something was missing. He didn’t impress me the way he should have. Even though I loved him, and even though he was very smart, I didn’t feel grateful enough to have found him.

There are so many different ways for relationships to feel off, let’s face it. It’s hard when you feel that something is wrong, but you can’t put it into words. You can’t justify it intellectually. It just feels wrong. You feel like you’re playing a role that doesn’t fit. Sometimes that’s because you’re just not ready for a lifelong commitment and you need to grow more on your own. Other times, you just know that you want more.

You have to stop thinking in circles and start asking yourself what you want from your life. If your life feels small with your boyfriend, that tells you something important. If you’re fixating on older men, that tells you something, too. I felt like that when I was younger. I knew my urges were shallow, but they pointed to something that wasn’t: a life that could feel big and bright and full of promise. A life that might feel like enough. A life I felt I was missing.

You should go out into the world, Unsure. You should live the life you want. It will be very hard to be alone at first, but eventually you will look at your life and you’ll say, “THIS IS WHERE I’M MEANT TO BE.”

Do the things you know you want to do at some point. Don’t put them off — your 20s are no time to play it safe. Go for the things that call to you. If they disappoint you, that’s okay. It’s better to check things out for yourself than to feel like you had big dreams that you never explored. You don’t want to spend your life plagued by doubts.

It will be hard to break up with your boyfriend. Maybe you could take a break first and see how that feels. I can’t tell you for sure what the right path is. But it sounds like a big part of you wants out. You want to know what it might be like to date someone completely different.

Doubt may never leave you altogether. I had smallish doubts about my husband when I met him; but I also knew without a doubt that if I ever ended things with him, I would look back and say to myself, “You made the biggest mistake of your life right there.” If you believe that you’ll feel that way, then proceed with caution. But if you think you’re more likely to look back on your life together and say, “I should’ve moved to New York,” or “I should’ve tried dating that really smart guy who made so much more sense to me,” you owe it to yourself to take those feelings seriously.

Can you defend your relationship in a court of law? It doesn’t sound like you can. Are you settling? If you have to ask, then you probably are.


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All letters to become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.

Ask Polly: Am I Settling?