What to Do When You’re Overthinking Your Own Happiness

Dear Grumpy Introvert,

This is maybe an anti-question. My backstory: After a divorce and then a string of unpleasant, failed relationships that left me feeling raw and really low, I decided to take a year off dating altogether. I used the year to really work on myself and to try to understand why I kept choosing the wrong people and ignoring red flags. I made a pact with myself that I would never again ignore my gut instinct about someone, and if I were to date again, it would only be someone who truly added to my life and the lives of my kids.

And then, after that year off men—and despite being an introvert who really hates small talk and dating—I met someone wonderful. Grumpy, he’s all that I could have asked for in a partner. He’s a single parent like me, and we are ridiculously compatible. We were cautious at first, but it soon was clear that this had the potential to be a really good thing. We’ve been dating exclusively for a while now, and my life is so much better with him in it. The crazy thing is, he feels the same way. He is honest and consistent and kind and compassionate and funny. He loves kids (his AND mine). His friends adore him, his family adores him, and his co-workers adore him. He is possibly the most thoughtful, gentle man I have ever met. And: He’s stupid hot. Like, so hot, I can’t believe he’s attracted to me. To top it all off, he smells like freshly bathed unicorns and newly ironed dress shirts.

He loves me, Grumpy. And I love him. A lot.

So now—obviously—I am freaking out. Because never in my life have I wanted something so much and had it actually happen. Things like this always seem to happen to other people, not me, you know? I keep looking for red flags, literally combing my brain for anything that would indicate that he’s not what he seems to be. And I’m not finding any. We share the same values and have very similar hopes and goals for the future. So Grumpy, can this really be happening? And if it is, how can I learn to accept it gracefully, and stop waiting for something terrible to happen?


Too Good 2B True?

Dear Too Good 2B True,

So let me get this straight. You had some rough luck in the love department, maybe for a long time. You decided to take responsibility for your part in attracting (and, it sounds like, hanging on to) the wrong people. You devoted a year to working on yourself, pinning inspirational self-care quotes on Pinterest, burning smudge sticks to exorcise your demons, consulting psychics—

[Ed. Note: She doesn’t actually say that she was burning smudge sticks or consulting psychics.]

[GI: Oh, please. You KNOW she was. There were probably casanova candles in there too.]

—and generally just reminding yourself of your own worth. Have I got that so far? Don’t answer; of course I’ve got it. That’s why they pay me the big bucks here. I KNOW STUFF.

I’m thinking, Too Good, that that love-sabbatical year you took for yourself was just the ticket. You cleared your brain and reset your heart. And then most unexpectedly, you met someone. Not just someone, but someone really special. I would say, “Well done, amiga!” and clap you on the back, but I sense that you’re still not sure you deserve the happiness you’ve found. And I can’t tell you that you do deserve it, because I just don’t think the world works that way. We all know many spectacularly lousy human beings—selfish, greedy, mean-spirited—who seem to have it all: love, luck, money, career, plush white carpeting that never looks dirty. And we all also know too many wonderful human beings—compassionate, kind, generous—who seem to be slammed again and again with appalling misfortune and can’t catch a break.

So let’s skip the “Do you deserve it?” angle, shall we? I’m smart, but I’m certainly not smart enough to make sense of the universe’s notoriously perverse ways of operating. The jury’s out on deserving. Maybe we deserve everything we get; maybe we deserve nothing we get, and it’s all random rain and rainbows.

Yes, let’s strip away this iffy existential question of deservedness, which I think is eating at you and complicating matters.

Let me answer your first (stated) question: Yes. This can be happening. In fact, I’m no expert (oh, wait…yes, I am) but it sounds like THIS IS VERY IN PROGRESS. Right now. In your life. Happening to you, as you brace yourself for the usual blast of disappointment.

Now that we’ve established that, yes, this is happening and you are not a figment of your own fevered imagination (and too many rom-coms), let’s tackle that second question: How can you learn to accept this gracefully and stop waiting for something terrible to happen?

Though grumpy as all get-out, I like a good love-manifestation Pinterest vision board as much as the next underemployed writer type with secret dreams of a man who brings her coffee and picks twigs of rosemary for the dinner she’s cooking on the terrace of their Greek villa overlooking the Aegean Sea. I have a soft spot for mushy love stories. I may be old-fashioned, but I believe previous generations got love and marriage right more often than we do today.

[Ed. Note: Please tell me you’re actually going somewhere with this.]

[GI: So impatient.]

Too Good, we are living in an era of overthinkers. I’m guilty of it, you’re guilty of it, and I bet that guy you’re so smitten with is also guilty of it. In this age of too much information (and the bristling, cynical commentary that usually accompanies it) most of us have lost the knack of something we were all born with: radical trust in the universe and the people all around us.

Don’t tell anyone, but I’m always reading interviews with elderly couples who have been married for decades (it’s a genre, if you know where to look). Their marriages aren’t perfect, not by a long shot. But time and time again, I recognize something in the words of these longtime partners that many relationships seem to be lacking today—trust in their choice of spouse, and simple faith that neither one of them was going anywhere. The longest-marrieds somehow managed—despite infidelity, illness, loss of children, infertility, wartime, poverty, you name it—to keep that radical trust in their relationships even when it wasn’t merited and even when hope was in short supply. They stuck around. They showed up. They didn’t overthink it. They chose their partners once (maybe not even very well, maybe hastily) and they simply decided to keep choosing their partners, every day, no matter what.

I find it impossible to be cynical in the face of such love stories. But cynicism and modern love are a pair nowadays, and have been for some time. I personally don’t support that union. Cynicism breeds prolifically in a climate of overthinking and second-guessing and bigger and better and what-if. But you know what doesn’t? Love. Love withers under the same conditions. So cynicism and love are pretty lousy bedfellows, if you ask me.

You’re not being cynical, Too Good. But you are overthinking. You’re honestly baffled by the goodness you’re seeing in this man you’ve found. I have a hunch he’s baffled too, by your self-knowledge and general all-around awesomesauceness. It sounds like you both have some battle scars from love affairs gone awry. But it also sounds like both of you have figured out a lot about who you’re looking for, and that just might be each other.

Heck, you’ve even gone so far as to vet his friends and co-workers and pay close attention to the details of the kind of man he is. And he holds up to scrutiny beautifully.

Guess what? You’ve done your due diligence, baby. Sounds like he has, too. I applaud you both for doing whatever bad-ass soul-searching got you to a healthy enough place to find someone truly kind-hearted and ready to love. If I believed in “deserved” I might even go so far as to say that you both do, in fact, deserve this stroke of luck and love.

I won’t say that. But I will say this: You can accept it by just showing up. Every day. You can’t predict the future. You can’t know what will come. But isn’t that a relief, in a way? It’s not your place to worry, because if you keep showing up and you keep trusting your choice and you keep loving this man, then you’re doing your part. You’re doing all you can, and that’s better than enough.

In this case, it sounds like that’s what he’s doing too. He’s made it clear: you’re his choice.

So it might take some time, Too Good, for you to stop prepaying for future worry. This is a process like anything else. It’s hard to be sad, but it’s also hard to be happy when you’re not used to it.

It just means you really, really care. But I’m a little superstitious when I’m feeling too happy, too. So I’ll tell you my trick: Every time I’m sure the universe has handed me something that feels too good to be true, I shut my mouth, I close my eyes, and I silently think, THANK YOU.

If I’m still panicking, I’ll say it out loud. As many times as I need to before my heart slows its galloping toward assumptions of doom and imminent disaster and humiliation.

There really IS something to gratitude. And when gratitude and radical trust in the universe go hand in hand, well, I’ve seen some pretty magical things happen.

Just keep showing up, Too Good. Just keep choosing him, and let him keep choosing you. You might start to forget all the disaster you were expecting to show up on your doorstep. Worst-case scenario? This relationship runs its course, and your heart takes another bruising. You’d STILL be better off, because you and this man are learning a heck of a lot from each other about choosing more wisely and staying the course—even when it’s terrifying. Best-case scenario? Well, I’ll just say here that I love a good wedding. Be sure to send me an invite.

Yours in love (and all the terror it inspires),


The Grumpy Introvert (otherwise known as Jennifer Mattern) is smarter than your average border collie, stronger than your morning coffee, and impervious to Comic Sans and all other forms of forced cheer. She has been an annoying know-it-all since the tender age of 8, when she first began correcting her teachers’ misspellings and offering copious amounts of unsolicited advice to her parents.

Have a question for the Grumpy Introvert? Write to her at [email protected]!