Dating, Decoded is a bimonthly advice column about single life, dating, and relationships, written by Hannah Orenstein.

   Here, Hannah gives her advice on dating again after a big breakup.


Q: Hey Hannah! I just broke up with my partner of five years a few weeks ago. We lived together and shared a pet. The breakup was one of those slow and painful ones in which it felt like our relationship was over for months before we finally ended it. Now that I’m single, I feel really excited to get back out into the dating world, but nervous that I’m indulging too much in crushes and DFMOs when I should be taking space for myself. But I feel pretty fine? I guess my question is: is it a bad idea to jump right back in given how serious my relationship was and how recently it ended? Also, do I owe people that information about my dating history? — Jackie


A: Hi Jackie! You say that you’re “really excited to get back out into the dating world,” but feel like you “should be taking space” for yourself instead. But why does that space have to involve sitting alone on your couch? Who decided that?

Heartbreak is such a deeply personal experience and it affects everybody differently. A breakup might look like pints of Ben & Jerry’s Chocolate Chip Cookie Dough ice cream, packs of tissues, an emergency appointment with your therapist, and a group chat exploding with messages like, “Are you OK?!?” Or… it might not. It could look like hitting up real estate agents to find a new place and figuring out how to split custody of your pet. It could sound like a sigh of relief, or feel like a new era of possibility. It can be scary and lonely and weird and exhilarating all at once. There’s no single right way to feel after a breakup. Your split is yours. You are the only person who knows which path forward is best for you. I promise.

People throw around the word “should” a lot when talking about dating, relationships, breakups, and sex. It’s easy to pass judgment on other people’s behavior, but when a breakup actually falls in your lap, you realize just how complicated and confusing it can be. Some breakups feel like getting pushed out of an airplane with no warning and no parachute. But yours was more like sitting in the last row of the plane after it landed on the runway. You spent plenty of time watching the passengers in front of you slooowly file out, waiting to stand up and stretch your legs. Of course you’re ready to get off the plane and on with your vacation!



It sounds like you spent months mentally preparing for your relationship to end and for your next chapter to begin. In many ways, you’ve probably already mourned what you and your ex had together and started thinking about what you’d want your near future to look like. It’s normal to feel a little nervous to get back out there again, but remember, it’s been five whole years since you last dated — that’s probably why it feels daunting. It’s OK if it takes some time to find your sea legs again.


You don’t need my permission to jump back into the dating pool, but I’m happy to give it to you anyway. Crushes are exciting! Dance-floor makeouts are fun! Swipe through Hinge, slip your number to that cute barista, send flirty DMs to your friend’s cousin’s neighbor you met at that Halloween party last year. That istaking space for yourself — you’re indulging an urge to explore other people and connections.


I will add one caveat: Crushes and DFMOs aren’t Band-Aids for heartbreak. If you throw yourself into new relationships to distract yourself from the pain of your last one, all you’re doing is stuffing your feelings down into some deep, dark place. But just because you aren’t letting them out doesn’t mean they disappear — instead, they’ll pop back up at inconvenient times until you deal with them for good. At some point, you have to let yourself feel sadness or anger or other prickly emotions. That’s how you heal and grow. So, if you haven’t already, try therapy. Journaling. Screaming into your pillow. Venting to your best friend. Working out your frustration in kickboxing class. And guess what? You can do it all at once: Date, heal, and take time for yourself in other ways, like getting really into the Bridgerton novels and twerking to the new BeyoncĂ© album.


You have no obligation to disclose your breakup to a stranger, so if you’ve traded five whole messages with a Bumble match or only had one or two dates with someone, keeping that info to yourself is all good. (And maybe for the best! You want to showcase who you really are, not just what you’ve been through.) If you sense things getting more serious, though — like you’re invited on a third or fourth date, or you’re starting to develop feelings — you might want to consider mentioning your relationship history. The word “mention” is key. This is not the time to give an hour-long Powerpoint presentation about why your last relationship ended. But it is appropriate to say, “My last relationship ended X weeks/months ago. We were together for five years and lived together. When was your last relationship?” If you two keep dating, there will be plenty of time to discuss more specifics (to the degree you’re each comfortable with) down the road.


Here’s the thing: There is so much advice out there about dating and relationships. Like, so much. And a lot of it is completely contradictory! For every person out there who expects you to be sobbing over Hallmark movies right now, there’s someone else who believes the best way to get over someone is to get under someone new. Another example: If you want a relationship, you have to put yourself out there, right? But at the same time, people always say you’ll meet someone when you least expect it. And here’s another: Some say texting is NBD, so you can write back whenever, but others swear by complex algebraic formulas to calculate how long they should leave someone on read.


One of the toughest parts of dating is taking in that tornado of advice and picking out the pieces that resonate with you. It can be tricky, and it can take some trial and error. I’m not saying that if you pick one dating philosophy to subscribe to, dating will instantly become a breeze, because unfortunately, that’s just not true. 


You’ll still run into scenarios that will hurt or feel awkward. But the more you practice trusting your own instincts, the easier it’ll become.

There’s only one person who knows what’s best for you right now. Luckily, you know just where to find her.