Dating Sucks: Getting the Most Out of Rejection

Dear Dating Diary,

In my life, there’s one thing I’ve probably fixated on more than any other topic. Rejection. I don’t know where this started. Was it in fourth grade when all my friends rejected my friendship because I was “different”? Was it in high school when all my pyscho friends and I became obsessed with which colleges we’d be accepted and rejected by? Or did it come sometime later, at the conclusion of my two significant relationships, both which ended in rejection. I guess all relationships end in some degree of rejection. Rejection is everywhere and I think about it all the time.

One of the upsides to the new swiping/tinding/app dating culture is that it streamlines the rejection process, making rejection less likely to occur and much more efficient/abrupt when it does. On Tinder, for example, both parties have to express interest in each other in order to be matched and chat. It’s like being at a bar filled only with cute people who think you are cute. It’s at once super harsh (i.e. swiping someone away when you don’t like how they look) and super humane (avoiding direct rejection from strangers).

As you know, I’ve been going on dates here and there. Like not a ton because I’ve actually gotten insanely busy over the past few weeks (lot’s of career stuff going on, like more than I can handle quite frankly). And I experienced my first real rejection. Rather than devastate me, it made me learn some things. So I’m going to share that story here.

I met Tom on Tinder, but I actually vaguely remember meeting him before at a party or something. I’d been following him on Instagram and I always thought he was cute and funny. Finding someone that is both cute and funny is INSANELY hard, especially in Los Angeles, a city FILLED with gorgeous people. I have a theory that most hot people aren’t funny because they’ve never had to work to gain people’s affection. Their whole lives, people were far too nice to them for literally no reason except their looks. People like me, who grew up struggling with their weight, acne, bad fashion choices, etc, tend to have better personalities because we could never rely solely on our looks to get by. So when you go out looking for a partner, look for someone who was totally gross growing up but somehow managed to swan themselves later in life. They have better personalities and are generally more entertaining than everyone else.

I’m calling this guy Tom (not his actual name) because he looks like a Tom of Finland drawing. Blond hair, mustache, dreamy blue eyes. Like maybe the cutest person I’ve ever seen in my life, both because of his personality and his looks. Our first date was at Kettle Black in Silver Lake, which is actually a really great date place. I had been going on a lot of dates with guys I hadn’t been that interested in, where the conversation was really hard to keep afloat, so I was surprised that he was not only way more attractive than I’d expected, he was actually really smart and fun to talk to. I liked him so much it made me nervous. I sent this text to a friend after that first date:

Clearly, I’m an actual lunatic. It’s very rare that I get excited about anyone so when I do I’m like “LET’S BE TOGETHER FOREVER I LOVE YOU. STAY WITH ME INSIDE THIS COCOON!” I tried to act cool, but I have no idea if I did. We went on two more dates. The first was an organ concert, which was cool but sort of boring. I spent the whole time having some sort of allergy attack, trying to pretend not to be snotting all over the place so he wouldn’t be totally grossed out.

The next date was a strategic mistake, which probably fast-tracked my journey to Friend Zone. We went to a game night at friend’s house. I have funny/amazing friends who like to make up their own games and play them. It sounds a lot dorkier than it is. Like it’s pretty nerdy but actually really fun too, especially when you involve whiskey. It was hard to talk to Tom at this thing though because we were on different teams and I ended up feeling like it was a dumb idea to invite him. The night ended with me driving him home and being like “Wanna come over?” and him being all “No thanks, some other time.”

We need to take a minute to talk about how sex works. Like now that I’m in the big scary single world I’m realizing I don’t get it. I have exactly no game and I don’t understand how you’re supposed to get people to sleep with you. This is important here because I felt like I was reaching a point with Tom where if we didn’t have sex it would fizzle and turn into something else completely and I needed him to be with me forever, until I die. But, like, how do you do that? I think being in a relationship for so long totally that I’ve totally forgotten how hooking up works. OR DID I EVER KNOW??? I’m thirtyfuckingfour years old and I have the sexual know-how of a Disney Channel tween. Sorry, I know you came here to read about sofas but I’m just baffled at my own lack of maturity/awareness here. Like how did I get this far in life? What the fuck is wrong with me that I can’t be a grown up that just asks for what he wants?

I had basically written Tom off as not interested until he sent me a gym selfie a few days later. I could be totally wrong here, but the way I interpret a gym selfie from a guy you’re massively into is “Hey look at my sweaty, gorgeous body, I obviously am into you enough to want you to want me, at least on some base level.” So I invited him to come over and make art with me at my place (I know, I should kill myself). He accepted, but then sent the most terrifying text ever. “Can I ask you something…”

“Can we hang out, just as friends?”

I was in a bad mood for the rest of the day. Like I knew I shouldn’t care but I did. I guess it’s impossible to escape that feeling of rejection, especially when you know how hard it is to find someone you’re interested in. The longer I’m in LA, the less I see viable options for potential boyfriends/lovers/husbands/dates. It’s not that there aren’t quality people here, it’s that they all have A.D.D. and are looking for something that maybe doesn’t exist (am I doing this?). With my two exes, I remember meeting them and thinking, “Oh, this is what I was looking for.” You know it when you see it. And I saw it in Tom.


After I stopped being all butt hurt about getting the “let’s be friends” text, I had a mini-epiphany. I don’t actually want a boyfriend and I don’t know what I really wanted from Tom. I’d been clinging to the idea of him rejecting me because I love rejection. I have a fetish for thinking of myself as an underdog. But in all honesty I just wasn’t the flavor of ice cream he wanted and literally have no control over what flavor I am (probably vanilla, FUCK MY LIFE). I guess with dating I’m just looking to find the part of myself that is desirable, sexual, and to just assert that I still exist, I’m not invisible.

I actually think it was really brave of him to be as direct as he was. In the age of ghosting, it’s pretty rare for someone to be fully honest. The usage of the “let’s be friends” trope felt a little contrived to me, but there’s actually no other way to say what he needed to say. I actually got a lot of laughs (like to myself, at home, alone) thinking about it because I’d invited him over to make art and I was trying to imagine what it would have been like if we’d been making art as anything other than friends. Like if we’d been doing it as fiances, would we be wearing wedding rings and tuxes? If we’d done it as boyfriends would we both be sucking on a super long piece of spaghetti while drawing until we accidentally kissed? The amount of time I spent daydreaming about how funny it would have been to have a performative/canoodling couple art-making night is kind of sad.

Ultimately what I learned from this particular rejection was how interested and obsessed with rejection I am. I seek it out. It fits into the narrative of my life that I’ve created in which I’m constantly victimized by various life situations. But this experience taught me that rejection is often based more on who the other person is than who you are. Their tastes and desires are colored by their life experience, and you can’t be held responsible for what they want or don’t want.

So I’m actually pretty happy with how this particular narrative ended. I made a new friend (maybe, until he reads this) and learned that I have an insane rejection fetish. I guess that’s one of the upsides of singledom and dating. You learn something new about yourself with every new person you meet.

Now if you’ll excuse me I’m going to drown myself in a tub of goddamn vanilla ice cream.


28 thoughts on “Dating Sucks: Getting the Most Out of Rejection

  1. Wait! I am so confused! What about that beautiful condo guy Felipe? Isn’t Orcondo his condo? I am so confused!
    (I love reading about your dating life so please share more about sofas, condos, and dating!)

    1. JT, you need to read the last few blog posts and catch up, super short story – condo guy dumped Orlando.

  2. OMG. You’re amazing. I’ve been following your career for years now, but silently. This new ‘dating analysis’ addition is so incredibly appreciated! I think you just described my personality too, in a way I haven’t been able to myself. I’m not in the same situation as you, but I love how much we all can learn from those ‘single & dating’ phases, whether by experiencing all those things first hand or like this, through other people. The whole rejection issue can also be applied to so many life situations and I’m facing that struggle too, just with other things. All in all, THANK YOU. I will excitedly follow your journey in the world of dating and what not.

  3. Once again, great read! I know this is an interior design blog, but I love your storytelling. I’m also 34, but you’re much more accomplished than I am, and I envy your talent and enthusiasm in everything you do, so don’t be so hard on yourself! You’re just a very PASSIONATE person, in life, career, relationships… you’ll eventually meet someone who can be as passionate as you are, until then, you do you, and don’t change beautiful self for anyone.

  4. I f****ng love you. Yeah, I came here to read about sofas, but I stay for your life story rambles. Your insecurities are inside all of us and I’m sure that every reader can identify with your story on some level.

    Plus, the self-realization that you love rejections because it fits into your narrative is VERYSELFAWARE and you should be proud. Not all of us are lucky enough to identify our flaws. Most of us think we’re perfect and have no idea

    Cheer, Orlando! Keep doin’ you (and keep sharing it because, obviously).

  5. I love that you came through this with a “lesson learned” and got to a good place. I’ve lived my whole life (38) with severe anxiety and can barely make a phone call to a friend because I’m sure they won’t want to hang out with me, and I don’t have that many friends. I want to work on my issues, but I also just want to sit at home with my dogs and not interact with people. Maybe you need a dog in your life right now 🙂 .

  6. It’s a rare gift to be able to write the way you are, and even though I’ve never met you, I’m guessing you match your words pretty closely – intelligent, funny, self-deprecating, sensitive. Being human is rough. Thanks for doing it honestly.

  7. You’re obviously anything but vanilla! That’s for sure! I love how honest you are with yourself (and your readers for that matter). You could easily go down the victim-road and that would be understandable, but I like that you found your Chateaulando and find the positive angle in things!

    And from one 34 year old (from the other side of the world) to another, dating does suck but it’s also fascinating what we can learn about ourselves! I think your revelation concerning Tom’s rejection is fascinating and so important! I have no doubt that you will eventually find what you’re looking for when you’re ready for it <3

  8. I just love you. And I love these posts. No one else on the internet is being this real.

  9. Just wanted to drop you a line to tell you how talented you are. Not just as a designer, but as a writer as well. You have a voice that is fresh, funny and relatable. Things might suck on the relationship front, but you are killing it on the career front.

  10. I agree with Lisa. Thank you for sharing this post. You’re a very good writer. There’s a book here maybe….

  11. Orlando, I love your writing style and sense of humor. One thing stood out for me in the love of rejection epiphany. Perhaps there’s a connection between the types of guys you interested in and the likelihood of rejection. Just a thought. And oh, you’re definitely not vanilla so put that one to rest 🙂

  12. Thank you for writing and posting this. I just realized that I am also obsessed with rejection; my rejection by men over the years is the main plot point in my single woman narrative. And having just been rejected twice in a short span of time, of course I have to connect that to every other time I’ve been rejected. I’ll be sure to bring that up in my next therapy session. 🙂

    Also, I use the cheese analogy instead of the ice cream flavor in the “personal preference theory.” I don’t think you’re vanilla. You’re probably a more challenging (but delicious and wonderful) flavor. In my cheese analogy, I’m Gorgonzola, and that’s not everyone’s cup of tea. I’m going to stop now because this is getting overly complicated.

    But seriously, thank you.

  13. Orlando … We’ve not met, but may I just say — I love you. Your raw honesty with yourself (the hardest!) and bombastic wit (hahaha, laughed out loud to the point of getting death stares from coworkers) wring my heart, because I so resonate with your journey, and somehow create breathing room afterwards. I feel less lonely, more open and curious to this painful, but hopefully meaningful, journey of life. Thank you for sharing.

  14. My issue has been different but the same. I have spent 20 years in a new town as a young Mommy. It has been a near friendless existence. People here at my age from 29-49 seem to be in a family 5 generations deep and have ALL of their friend sorted out from their alma matters. So, I have not fit in. But then again, rejection has been the story of my life. I had friends growing up, but was always kind of everyone’s last resort. But here’s the thing. And it isn’t what you think and it’s not what you want to hear. In 2014 I went through a period of insomnia. I spent what I call my 40 Days and 40 Nights period listening to music, dancing, looking at art, reading poetry, pinning, etc all in the middle of the night when I could not sleep. And God showed up. I kid you not. He made me feel. No KNOW that I was beautiful (47 yo, five kids later), ACCEPTED, and LOVED. I am telling you that I literally grew a spine. I walked taller and felt confidence I never had in my life. I had joy! Long story shorter than it could be, I later heard a conference speaker (Todd White) say something that summed up the end result of my encounter with the Living God: “If you are accepted, you cannot be rejected.” I am still human, I still get lonely, still get my feelings hurt, but never again have I been the same. It is absolutely true that if you absolutely know that God is FOR you and loves you, he shows you your own beauty and all of the beauty around you and you just don’t receive the rejection that comes from others. Not that someone very close you will never hurt you again, you just know that the LIES are lies and that you are absolutely and completely loved. Praying for you to find Him in this season of your life! And if you hate me for the god-talk, SOOOO what. He loves me and He loves you.

    RubberChickenGirl (and Jesus)

  15. I just want to say that you are incredibly good looking. I’d say “I think you’re incredibly good looking,” but I’m pretty sure it’s an objective fact, not just my opinion. If I were a gay man instead of a straight woman, I’d be way too intimidated to talk to you.

    Thanks for sharing your story. I love this combination of interior design + life stuff. Interior design blogs can be too much perfection sometimes. I like decor porn as much as anyone, but it’s refreshing to get a dose of real life human issues alongside it. Best of luck in your search for love!

  16. Oh my God I was so hooked reading this because I feel like I’m in the exact same place in my life right now. But I’m totally finding that rejection hurts so much less when they’re upfront about it! Ghosting is hurtful and rude as and people that do that suck! Like it needs to stop. Keep getting out and do YOU. If I were a gay man (and not a midwestern white girl) I’d be waayyy too intimidated to talk to you

  17. You are not getting my sympathy. At least, he offered to be friends with you! Do you really wanna know what hurts the MOST? When a gay guy totally rejects you (= he doesn’t even wanna be friends with you) and he does it ONLY because he doesn’t find you cute or cute ENOUGH, not because you are dull or stupid or unkind. When you meet a guy and he doesn’t even give you the chance to properly introduce yourself, and within 10 minutes he’s already made up his mind he is not interested in keeping in touch. How’s that for rejection? It hurts as hell. I’ve had gays do that to me. These are the same men who like to say “friends come in all shapes and sizes”. These are also the same men who often claim to be “professionals”. I am looking at your photos and I can’t imagine why anyone would want to reject you, at least based on looks only. In my opinion, you are the epitome of cuteness. This leads me to believe that men in LA must be insanely picky, which is the reason why I would never want to live in that city. Trying to constantly live up to others’ ridiculously unrealistic expectations gets tiring and irritating after a while. When it comes to dating, big city life is a nightmare. Living in a big city means more gays, bigger competition, greater superficiality. Unfortunately, with the proliferation of sleazy hookup apps (I don’t call them dating apps), things can only get worse. There will be more rejections and more rejections and more rejections because the “grass is always greener on the other side”. You can keep on meeting men, hoping one day Mr. Right will come along, but in the gay community specifically (not so much in the straight community) this can be a super long exhausting nerve-racking and disheartening process. Good luck.

  18. I’m a 26 yo woman trying to date in Brooklyn and it’s sheer agony so I completely empathize with both this story and your lack of hook-up know how. Also, even though I went into this knowing it was a tale of rejection, I found that gym photo misleading within the context of the story sooo…. don’t think you’re the crazy one there. Anyways, big fan, sending you love during your heartbreak and thinking if you were an ice cream flavor it would likely be talenti salted caramel which if you haven’t had you should immediately waddle your way to a store and get some.

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