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  • Sexual Wellness

Going Through a Breakup? Jemima Kirke Weighs In

Tender Tips is a new advice column by Jemima Kirke, dishing out unfiltered guidance on everything from love and sex to all the messy moments in between. This month, she’s answering reader questions about how to get over a breakup—no fluff, just real talk.
Hannah Jackson Published: January 14, 2026 | Updated: January 14, 2026 6 minutes read
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For her latest Tender Tips column, our resident truth-teller reflects on the healing process.

How do you believe in love when you only do hookups?

That’s a bit like asking how I’ll ever win a game of pool if all I ever do is take practice shots on my own. If you keep showing off at the pool hall, eventually someone’s gonna throw money on the table.

What helps you stay so present and playful?

Having someone’s undivided attention, lots of praise, and satisfied expectations help me stay regulated and maintain a pleasant disposition. “Present and playful” is a stretch.

I found out that my dad cheated on my mom, and I’m angry at him. What should I do?

Dear Pollyanna,

You’re out of your depth, and I’m guessing over the age limit. The last thing your parents need right now is you butting in with your opinions about their relationship. Your parents have been dealing with their issues since before you were born (arguably, that’s what pushed your father to cheat in the first place), and their relationship has dimensions that you don’t know the half of. They’ve spent your entire life considering your feelings and hiding shit from you. Now that you’re grown, the best thing you can do for them is permit them to finally not consider you in their affairs.

I am a 33-year-old woman who is still single and surrounded by marriages and pregnancies. How can I not want to feel bad about myself?

Don’t be ridiculous. Pull yourself together, woman! This is hardly the end of the road. If you’re not already in an assisted-living facility, I recommend that you check in. Elderly people find love in nursing homes all the time.

My ex-boyfriend of many years, who I broke up with a year ago, has popped back up again. It was a violent and scary split. I’ve made a lot of life changes since then, and we’ve both done therapy and have been working on ourselves this whole time. Should I try this again?

You can. But if you really have changed, it won’t be the same relationship. Compatibility and attraction have a lot to do with the circumstance. You might not be well-suited for each other anymore. Might I add that the concept of “working on oneself” has always struck me as delusional, if not slightly dishonest. It’s often used to validate a bad idea. “If I do a bunch of work on myself then can I have it?” There’s a transactional quality to it. People can and do change all the time, but we aren’t cars. A diagnosis, an instruction manual, and a set of tools aren’t all we need. There’s a whole lot more that’s out of our hands. Change has its own terms, and rarely do they align with our preferences.

What’s your opinion on getting back together with someone? In a normal people situation.

Normal people don’t get back together with their exes. That being said, stranger things have happened. I can’t measure the risks for you, but there’s nothing wrong with a bad idea every now and then. Once, long ago, a friend of mine got engaged to someone she barely knew. Her family was horrified and tried to intervene, but I was all for it. I wanted to scroll through pictures of napkin rings and dining chairs and all the heinous dress options. I wanted to write up a blacklist and convince her to do an all-night party at Sinatra’s former home in Palm Springs. She is a smart, hardworking adult who was excited and swept away. We are all entitled to pull a wild card sometimes, to stack the odds against ourselves and hope that it works out. Because it might. You never get what you plan for anyway, so to hell with it.

What do you do when the guy is hot but emotionally unavailable?

Emotionally unavailable is the medical term for uninterested. Unless he is emotionally unavailable in the way that my children are when they are overtired and unable to regulate themselves. Pick your poison. If you’re into that sort of thing.

How do I break it to my mom that I’m dating her ex-boyfriend from 17 years ago? They were together for two years, and I was barely a teenager at the time.

Brutal. You could do it with a cute prank. Tell her you’re having an affair with her current boyfriend or husband (assuming she has one), then, say you’re joking and tell her who you’re actually dating. It will be such a relief that she may not even mind. If her current partner is your dad, this will work even better.

What’s the greatest lesson love has taught you?

It hasn’t taught me shit. I’m thoroughly confused.

Do you believe in magic and tarot? One tarot reader told me that a jealous woman is casting a spell on me for the worse. Have you ever been told something like that and how would you react?

I would immediately purchase another session. Then probably another one to make sure I cover all my bases. Beyond that I’ll buy as many as are necessary to stop this sorceress and undo the hex she hath cast upon my soul.

How do you tell if it’s just a crush or real feelings?

A crush is a real feeling. There are all kinds of genuine feelings that fall under the umbrella of love. The epistemology of love is a hot topic, but how can people be so certain of what counts as “real love” and what doesn’t? Wouldn’t it be great if there were an expert you could go to? Like when you bring your jewelry to a diamond dealer or gemologist to have it appraised and they look at it with that tiny microscope and do these curious little tests. They show you clues like cracks, dirt, lines, and bubbles. They’ll weigh things, and you’ll look at their face to gauge if it’s impressive. They’ll tell you that the stone is porous or soft and you feel surprised because it feels perfectly firm and smooth to you. They hold it up to the light and it shines and you think, Oh, isn’t that beautiful! And they tell you it’s not shiny at all or it’s not the right kind of shine. Not compared to the other one. See? But you feel clueless because they all look so pretty. Then you think of an old rhinestone bracelet you used to have and how dazzling that was and all it cost you was 15 bucks…where did that one go? I wish I still had that. I wonder who has it now? I’d do anything to find another one just like it. Or have one custom-made. Or search high and low for that very one.

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About The Author

Hannah Jackson

Hannah Jackson

Hannah is a fashion writer at Vogue. She wrote for in Elle, The Cut, Harper’s Bazaar, Rolling Stone, Architectural Digest, W, and elsewhere. She is based in New York.

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