Thoughts | You Should Date a Thoughtful Man


Navigating life after a long-term relationship is something I’d never wish upon anyone. It left me feeling so inexplicably empty and without a sense of identity; I honestly thought I’d never recover. You forget you’re your own person because you’ve become so consumed with putting someone else’s needs before your own (and that’s not a bad thing, it just takes some time to adjust to that absence when that other person drops you like a hot potato).

With time, I’ve come to see that the difficult moments that followed my breakup were actually blessings in disguise. As happy as people might seem wrapped up in the arms of another, the blunt reality of being in a relationship is that it gives you tunnel vision. Like it or not, if you’re seriously committed to someone, that person is all you see as:

Your friend.

Your confidante.

Your lover.

You name it, that person is likely your go-to for everything, both silly and serious. They’re the person you reach to call when you’ve got something to celebrate, as well as the one you lean on when you’ve had a shitty day and just need to drown out the world with ice cream and Netflix. They’re the person you can just exist with in silence in a car parked by the beach while it relentlessly rains outside. They’re the person you hope you’ll never have enough time with, because forever really isn’t for forever.

I thought it’d take me a lot longer to get over my last breakup, but the truth is, there were problems we’d been ignoring and compromising on for quite some time. But that’s what you do when you really love someone, you do whatever it takes to make it work; that’s what carries you through the rough times (or so I thought). But the reality is that theory only works if both parties are on the same page and fight for what they’ve got equally as fiercely.

You can’t have one party giving it their all and the other just staying because they would have to exert a modicum of effort to leave. I thought it’d take a lot longer to get over everything because the only other breakup I could recall in recent memory was six years ago…and it took an entire year to get over his (great) ass (he played catcher on our college baseball team). He was a two month flame that fizzled just as fast as it started (oddly enough, right before I was going to go to my first Stagecoach festival). Even though the good morning/good night texts only lasted a matter of weeks, it took 365+ days to get over the idea that we were over before we even really started.

I thought it’d be the same for this breakup, but I couldn’t have been more wrong. It took that night in the hospital and the morning after for me to realize that I wasn’t important enough to him to ask if I was okay. It took adjusting to the uncomfortable reality that life doesn’t pause when things fall apart, so you just have to keep going, even if that means slowing your pace down for a little bit so you can catch up (eventually…I’d say I’m 85% there).

I’d liken that night in the hospital to a light switch. I went from embracing the notion of “’till death do us part” one day, to incapable of being able to fathom a friendship the next. It’s the oddest sensation to essentially become strangers overnight.

I think it lessened the blow on my end because it wasn’t my choice to end things and in the wake of the first twenty-four hours, I begged him to reconsider – I was that committed, even though I knew a future with him would forever be riddled with his family’s unbridled jealousy and inexplicable hostility towards my education and upbringing. It wasn’t a future I was happy with, but I thought that with enough time, it could’ve gotten better if he ever grew to love me in the way that I loved him – unconditionally.

Herein lies the blessing: you shouldn’t settle on hope. I had held onto hope for so long, I’d lost the ability to value my own happiness. You have to find someone who loves you without reservations, and that night in the hospital made me acutely aware of that and that it was something I did not have with him.

This loss taught me, more than anything, that I was/am capable of loving someone completely. It forced me to acknowledge that the guy I was with couldn’t reciprocate that love, and oddly enough, that is single-handedly what’s made it easier (and I mean that lightly, because breakups are never easy) to close that chapter and know it’s a story I won’t be picking up in any way in the future.

I wasn’t expecting to meet someone so soon after all of this, but the truth is being with him is effortless. Our first date was four hours of rambling conversations over beers he’d ordered at my suggestion (who trusts a girl about what beer to get?). He was such a good sport when I told him I’d scheduled a date with someone else right after ours (oops). He even humored me when I asked him what my competition looked like on the dating app we’d met on & he let me swipe for him right there at the table.

I did the same (let him see & swipe for me) & probably shouldn’t have because he didn’t need to see the endless likes and dead-end conversations on my profile; but maybe that’s what prompted our second date to happen in a different city across the country the following week? I took his half-baked offer to meet him on a work trip and booked my plane ticket the next day.

Our second date was honestly one of the most spontaneous risks I’ve ever taken with a stranger, but I think it’s one that has potential to become something really good. As much as I abhor dating because it exudes opportunities to be inordinately frustrated, I think it’s equally exciting with its endless opportunities to meet people you might otherwise never cross paths with.

There’s no way to know if a swipe will turn into anything – but if my two dates that night are any indication, one is a dating horror (not really, but it was 10/10 on awkward) story, the other, an opening scene to a pretty good movie and/or great book.

Did I mention I saw it snow for the first time while I was on that trip? Yep, it was pretty magical (in fact, I think I remarked how it was like being a character in a snow globe… which is pretty cool, because I used to collect them as a kid). Which brings me to the point of this post. Not too long ago, I wrote a post about a favorite article of mine. You can read it here: Thoughts | You Should Date an Illiterate Girl.

The gist is that you can find a relationship that checks that box of “in a relationship” without much difficulty, but you might have to search a little harder to find one that challenges you to become a better person, pushes you to do more, and asks you to think a little deeper than you normally would/could.

These last few weeks have prompted me to write a response of my own, because this guy is anything short of an ordinary online dating find.


You should date a thoughtful man. One who doesn’t open with “what’s in it for me.” Someone who is genuinely interested in who you are, what your story is, and where you want to go – personally, professionally, and everything in-between.

Date a man who makes you want to push him away because it scares you how effortless it to be with him. He might mess up and break your phone, feed your dog pepperoni pizza, and puke all over your parents’ kitchen bathroom, but don’t let that end things.

You might try, but he’ll make you see that shit happens and it’s getting through that that makes you want to be with him even more. He’ll notice the details other guys overlook, like the glittery eyeshadow you made a point to put on before going out together.

Date a man who takes pause when you don’t answer a question how you normally would. Obviously something’s bothering you, but he could have just as easily carried on without asking you what’s up. He will patiently wait until you’re ready to talk about it and won’t pester you a moment sooner.

Be with him because when you ask if it bothers him that you haven’t deleted pictures of your ex, he tells you “no” because that’s a part of your story. Had you not met the guy before him, you wouldn’t be here, holding his hand and asking him to take a risk on you with his heart. Hold him close when he tells you what scares him because you have different fears and you two can support one another through them, separately, and together as a couple.

No one knows how long something like this will last, but pursue it honestly and completely without hesitation, because that’s what a thoughtful man will do for you. He’ll speak to you without hesitation about a future together, because the reality is that could very easily become a possibility.

He’ll never let you struggle in an airport with a carry-on full of books, because you wanted three options on the plane in case you didn’t fancy the first two. He’ll never let you hang up the phone if you’re upset (even if that means talking until four in the morning after said pizza/phone/hot mess express fiasco), because you mean too much to him leave things unresolved.

Be with him because he’s excited to tell his family about you; he wants to introduce himself to your mother and stands up without prompting when he meets your father. Ask his friends about him and you’ll only hear good things, because that’s all he exudes. Invite him out with your friends because he’s genuinely interested to learn more about your life. You shouldn’t be surprised when your friends light up when you ask their first impressions of him and they won’t shut up about how amazing and cool he is.

He might, no, he will have flaws; but that makes him even more worthwhile to pursue because you’re flawed too. The greatest love stories are the ones with flawed heroes and heroines who make mistakes time and time again, but you still aspire to be like them because they recognize their flaws and have to work twice as hard to persevere through them.

Date a thoughtful man because we all need to be reminded that we’re worthy of a connection with someone that’s unlike anything we’ve come across before. Don’t look for perfection. It doesn’t exist. Look for someone who makes you weak in the knees when they hold your hand. Someone who makes you smile from ear to ear when you see them, so hard your cheeks hurt when you go to sleep at night. Someone who reminds you to be a little (or a lot kinder), even on your most difficult of days. Someone who reassures you that it’s okay to fall apart sometimes, because that’s how you get stronger.

More than anything, date a thoughtful man because you’ll find yourself again and celebrate the things you love about yourself, even if others before him didn’t. He’ll never ask you to change. He’ll never tell you you’re not enough, or too smart, or too outgoing, or too ambitious. He’ll always be there as long as you’re always there for him…and you should be, because he’s like one of those serendipitous finds you only find a few times in a lifetime (if ever)…and if/when you find that man, hold on tight and don’t let go.


Author: 2LWithIt

Spoonie Adventures in Books, Beauty, & Bullshit I'm a twenty-something year old recent law and business school grad living with a chronic health condition. Follow along on my shenanigans.

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