Dating Sucks: How to be a Good Friend During a Breakup

Dear Dating Diary,

I was in a coffee shop yesterday, in a part of town I never go to (near Burbank? I have no idea where I was) and I ran into someone I hadn’t seen in a long time. It was a close friend of my ex-boyfriend’s (X). I was at this guy’s wedding six months ago. We had him and his fiancé (now wife) over for dinner a few times. He wasn’t a best friend or anything, but definitely someone I’ve shared a drink and a laugh with more than once. But I kind of froze when I saw him. Had X told him we’d broken up? Should I say hi? Would saying hi mean I had to explain the whole painful situation again? Little moments like this come up a lot and I’m never quite sure what to do about them. I ended up avoiding eye contact and walking out of the coffee shop.

I felt kind of guilty about it when I left. After all, this guy was gracious enough to invite me (by way of X) to his wedding. I’ve been in the house he grew up in, met his mother. But on further thought, I kind of think I did the right thing. It’s likely that he knows X and I aren’t together and felt equally as awkward at the prospect of talking to me. We had no common bond aside from X. So not only did I protect myself from an awkward moment, I also protected him. The reason I bring this story up is to highlight how often ghosts of exes can arise, how even if you do your best to avoid thinking about someone you used to love (still do?), somehow you’ll be reminded of them over and over.

Sidenote: I’ve been listening to this Tegan and Sara song over and over and it’s kind of the perfect breakup song. Best lyrics: “YOU WERE SOMEONE I LOVED THEN YOU WERE NO ONE AT ALL.” The perfect way of describing how jarring it is to have someone be your partner then have them be basically nothing. Life is fucking weird and confusing and terrible.

As another wise songstress once said, breaking up is hard to do. But with the help of some friends, it can be a lot easier. Today’s topic of conversation is how to support people going through a breakup.


The most jarring part of becoming single is having tons of time to yourself that you’re totally not used to. I hate it, because every time I want to share a meal with someone I have to text like eighteen friends before I can find someone who’s available to hang. And then I have to deal with all my friend’s annoying busy schedules. When you’re in a relationship you have an automatic buddy to hang with every day, to snuggle with on the sofa, to give back rubs to. GODDAMN I MISS THAT SO MUCH. Another element of being in a relationship is that you tend to fall off your friend’s radar for hang outs because you don’t tend to go out as much during the week (I’m generalizing here based on my own experience as a heavily-nesty person). So when you break up no one thinks to invite you to weekday hangouts anymore, and so social planning falls totally on you. Which is understandable, I sound have been better at reaching out when I was in a relationship.

Your recently-dumped friend will appreciate being invited more than you might think, even if they don’t accept the invitation. I guess this is also just a general rule about people. Everyone likes to be invited even if they don’t want to come. It’s human nature.


I know, I KNOW. I’m being such a millennial baby for using the word “triggered.” I’m a literal snowflake that just melted. But it’s necessary here. For some reason, the question “Did he say why [he didn’t want to be together anymore]?” to be a really painful/confusing one to answer. The reason being that it kind of makes me relive the moment of being dumped over and over again and try to understand it, which I still don’t. I’m sure there people out there who have recently broken up who wouldn’t mind that question, but to me it feels a bit invasive and confusing. A question that is generally better-received and more appreciated is “How are you feeling about everything?” or “How’s your heart?” Yes, these questions sound completely ridiculous and self-helpy but they relay your interest and sensitivity to your friend.


Asking a newly single person if they’re dating is a way to make them feel like they’re sexually viable and still attractive, things they might be feeling doubt about. Don’t do it in a way that makes them feel like a loser if they’re not dating, just ask if they’re seeing anyone or putting themselves out there. If they’re not dating, fine. But you asking them about it will make them feel like their is hope for their dating life and their future.


The best thing you can do in a breakup is improve upon yourself and show self-care by beautifying your space. Taking your dumped friend shopping for clothes or homewares is an easy way to say “Hey, you’re still a person. The future is still fun.” Inviting your friend to go on hikes or day trips is another way to get a dumped (or just generally depressed) person out of the doldrums. These simple things will make your friend feel cared for.


I’m pretty thankful that discussions about depression have emerged from the shadows and are getting more and more socially acceptable to talk about. It’s probably because I live in LA and have lots of artist/writer/actor friends who are in-tune with their emotions but it’s totally not out of the ordinary for me to ask a friend “Are you feeling depressed” and let them answer honestly. Giving someone permission to talk about their feelings of depression relieves them of the burden of having to bring it up and also lets them vent about it. Depression isn’t something to be ashamed of or kept a secret, the more hidden it is the more insidious. Sidenote from me: I’m not depressed right now. A lot of people have been asking me if I am, based on my dramatic Instagram captions and blog posts. What I’m feeling is more a general feeling of anxiety about all the personal tumult combined with the career upheaval (as I mentioned yesterday, I no longer have a day job or a steady paycheck, so I’m in a space of great career potential and great financial fear, which is pretty anxiety-inducing and a lot to deal with in addition to all the emotional breakup stuff and the moving/renovating/logistical stress of the last few months). See? I just shared my feelings and now I feel better. Now your turn!


The above are all things my friends have done for me during past breakups that have been immeasurably helpful. I’ve said it before and I’ll say it until my head explodes, my privilege in life has been the incredible, supportive, creative people I know. I’d also like to hear your stories. I’d love for people to comment about things people did for them during a break up which helped them heal. Please leave your suggestions in the comments.


A note on these ‘Dating Sucks’ Photos: People have been asking me about the portraits of me that accompany these posts. I started making these self-portraits for a few reasons. One, and I’ve mentioned this before, part of me felt invisible and disposable after getting dumped. I’ve been struggling with my weight and self-esteem issues for a while, and even though I had to be on camera for a lot of projects (like my Homepolish x Method YouTube series), I found myself constantly dreading seeing images of myself. Part of this series is figuring out how to face myself again. And another part is just exercising my photography skills. I studied photography in college but I’ve never done it professionally, so this is an opportunity for me to grow artistically while learning to get to an OK place with looking at myself.

21 thoughts on “Dating Sucks: How to be a Good Friend During a Breakup

  1. Two thumbs up for honesty and taking the time to figure things out. From where I sit it seems your ex was ruled by a pretty standard issue West Hollywood narcissism and you ended contaminating his world by trying to make “us” more important than “him”. Sad you’re suffering for that but in the end there will come a time when you can see it was “good riddance” despite the trauma. You’re a handsome, intelligent, creative and humorous guy. I can’t see this not ending well for you.

  2. Oh Orlando I think you are cute and I would go out with you if you were straight and I wasn’t already married. Be strong internet friend.

  3. Dude, I love this article for friends going through a crisis of any kind. Hoping you continue to be supported by your community of friends!

  4. You are awesome. I just want you to know I am on your train no matter where it’s going.

  5. These suggestions are just perfect for anyone with friends who need to feel valued after a breakup or a job loss or any kind of life event that affects feelings of self worth. Thank you for sharing so much of yourself.

  6. Thank you for sharing this. I am always moved by your words (on this blog and on Instagram). I have a close friend who was blindsided with a breakup right before she moved away. It’s been so hard to know how to support her (and still keep the silly, non-serious side of our friendship thriving) long distance. So thank you for sharing your experience on what’s nice to hear and what just stirs up the bad feelings.

    Also, I love your self portraits! I’m a photographer too, and the self portraits I did in college are by far the most meaningful work I’ve done. To me, anyway. Probably no-one else. But art is kind of all about narcissism anyway.

  7. Orlando-
    I don’t know you, I started reading your blog because of your guest posts on Emily Henderson and I am so happy you are back blogging regularly. I too went through a break up in November that completely took me by surprise and I have related to different things you have shared. I have taken strength from your honesty and your posts and I appreciate your emotional integrity. I look forward to reading many more posts!
    Thank you,
    P.S. I also bought a new rug and couch and am looking for dining chairs and switched bedrooms so yeah, home improvements help a lot and keep you busy!

  8. I usually never comment on blogs but just wanted to say I am loving the more frequent posts lately, and thanks so much for opening up more about your own life–your writing is poignant, relatable, and hilarious (a rare combination).

  9. I will say it again, I love that you are posting more! Also happy to learn more about the man behind the greatest home design instagram account of all time

  10. It is hard to understand your viewpoint that you have a rough time with your physical self. You are almost ridiculously good-looking. And then smart, funny, and talented? I mean, come on!!!!
    (My son has one very, very, handsome friend and you kind of look like him.)
    I love reading your blog, and I’m pretty sure that your next position will lead you to really great things. All the best!

  11. Good advice for any friend going through any kind of tough time. It’s a bit like grieving, actually very much like grieving. People don’t always know how to handle tough questions or talk at all, so giving this feedback is great. I’m glad you have a project (chateau), but make sure you keep social, too. And clearly, that’s hard too. Volunteer somewhere meaningful, it will get you out of your head and help you feel better.

  12. Okay…so firstly, so sorry to hear about your breakup. Breakups are the worst! Silver lining: Your blog has never been better! Probably not super comforting to hear right now….but your authenticity is charming and adorable and makes you vulnerable and relate-able. All the things that some man out there will see and love you unconditionally for. But until then…can you please listen to Little Big Town’s ‘Better Man’. SUCH a great breakup song….even if you don’t like country music (I don’t). But that is what I was thinking….you deserve a better man. Done.

  13. Great post, these tips are (unfortunately) something I can use in my life due to some breakups my friends are going through. I also really try to text them and tell them I am thinking of them and am happy to be their friend, sometimes when people are not ready to go out and try to have fun yet, they still feel cared for

  14. Orlando,
    I think a break-up is a little bit like a death, but you feel hurt instead of bereaved. Anyway, when my best friend’s husband died, I just kept asking her what she needed from me, and she was honest enough to tell me. Most of her answers surprised me. I wouldn’t have thought of the things she asked. The point is, ASK!

    You have many anonymous people cheering for you. Please remember that we care.

  15. Holy shit, how many times I have heard “but you’re already SO HOT”… from my lovely lady friends, chased with a bitter shot of “what a shame” under their breath. Life is not (underappreciated movie) The Next Best Thing – I am fortunately not Rupert Everett, and you are unfortunately not Madonna. Ladies, it’s super nice to hear, it’s comforting, we appreciate it – especially during brunch when I’m doing splitsies with you on the tres leches French toast after I’ve eaten my own plate of huevos. But it is as effective as my mom saying I’m hot.

    What counts is your empathy, and you have tons of it – and I see it here in the comments and it is glorious. Thank you for asking about our hearts over a glass of wine, for standing behind us during yoga so we don’t see how good your “flying crow” is and for not wearing Lululemon stretchy pants during brunch so we don’t have to drop you from our friends list (because that friends list is getting smaller by the week – honestly ladies, wear real clothes). And thank you for being curious about the gay experience so we can share bottom/top jokes with you without having to explain it. KEEP IT UP!

    Orlando – advice from a stranger, avoidance is easy. Acceptance is tough. So what if you had to tell that friend of X at the coffee shop that you and X are no longer together? It is part of your acceptance to get on the road to recovery – for yourself. Avoiding it means that you are afraid that friend of X may judge you for something you did. You didn’t, X decided.

    Being vulnerable is OK too, we can hurt and we can grieve but we have to move on eventually. And we find outlets for pain and grief, if you’re finding exercise is therapy then more of it – also, nothing hotter than a revenge body.

    Lastly, you are not invisible. You are enough. (That’s my daily affirmation, thanks to my therapist – on loan until you don’t need to say it).

  16. What an excellent list! The only thing I would tread lightly with is asking people if they’re dating. My ex and I lived together for 7 years, and in that time dating apps came out and the whole dating world seemed ruuulllll different and intimidating after we broke up. People constantly asked me if I was dating and I knew I wasn’t ready but people kept insisting on asking and telling me that I had to date, it was so easy now, blah blah blah. I found it really difficult and strange, and it just made me feel worse about myself, like I was a complete doof.

    Anywhoo, I really enjoyed reading this and related SO MUCH.

  17. I love the photography project. When challenges and anxiety have become the bffs that never leave, simple projects like your self-photography are the solution to getting to a better place. These new activities can feel so silly to me when I start out but I try to champion myself with every positive sign of growth-like, I never would have done x before that bad thing happened to me. I’m changing for the better. Love the revamped blog, love the posts.

  18. I really appreciate your candor in these personal posts. I saw an Instagram post from you around the holidays and while I was sad to hear of your breakup it was helpful to know others could relate to my own sad holiday feelings. I was broken up with in October.

    I love the “How is your heart?” Friends, please listen to the answer. I’ve hated the “Are you dating yet?” It was asked of me within 1-2 months and has felt like my dating is the proof to the person asking that I’m okay. My goal is just to feel good. I thought I would spend my whole life with my partner so that question, to me, has felt very insensitive.

    Just my thoughts and so glad you’re sharing yours! Hugs!

  19. Orlando, your words touch me with your sadness and pain over what has happened to you. Keep writing. Your truth heals.

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