Dating Sucks: Everyone Is Looking Up

Dear Dating Diary,

Something I’ve noticed about myself is that I’m constantly comparing myself to people who are more successful than me, who have more money, who are more in shape or seemingly happier. There is a natural human tendency to compare ourselves with other people we perceive to have more or be more than ourselves. This permeates into the dating world and affects the way we interact romantically, but today’s conversation isn’t confined to dating. It’s more about an issue I see in myself and in people around me. The issue is that we can basically never be satisfied, that we will always look around and see someone else with more, and that affects the way people approach dating. First, I’m going to discuss what exactly I’m talking about, then I’m going to discuss its negative effect on the dating world.

I’ve been part of the blogger/influencer/designer/personality world since I was on a TV show with Emily Henderson in 2010. I’ve seen of lot of my peers in that community grow and flourish in the past seven years, and I compare myself with them constantly. I’ll see other designers I know get big brand endorsements or get their own furniture lines and I often have a “why not me” type reaction. I think there’s something natural about being a feeling a bit like you’re falling behind and comparing yourself to people in your field. Sidenote: I’m in a super weird field. It’s just a bunch of people who write blogs/books/instagrams about fluffing pillows and choosing wall colors. It’s not the actual real world. I’ve also been involved with a company for the past three years so I couldn’t take on the type of career-expanding moves that many of my peers have. Emerging from my full-time job and being on my own again, I’m definitely getting a “FUCK I AM WAY BEHIND” feeling.

As I’ve whined about before, I got dumped and laid off in quick succession recently. My financial situation has gone from pretty great to pretty terrifying pretty fast. My overhead (rent, car, student loan payments, retirement accounts, etc) is based on an income that I no longer have, and I’m struggling to figure out how to set up my business and life so that I am making the same amount and more, getting closer to my financial goals (mainly buying a place so I can stop throwing money away on renting, because renting is the worst). I’m trying to see all of this as an opportunity for growth rather than a loss, a chance to really build the business I want to build and do the things I want to do. But in all that of course there is a tremendous amount of risk and financial fear. And instead keeping my head down and concentrating solely on my own position, I’m of course looking around thinking about what everyone else is doing, wondering how they run their businesses and make money, comparing my achievements to theirs. I don’t consider myself competitive at all, but maybe there is part of me that is.

In all of this, I’ve noticed a trend in the people I am comparing myself to. They’re all [perceived by me] to be more successful than I am. But I keep having experiences that rip me out of that, and it’s been kind of a blessing. Being that I live in Los Angeles, a city with one of the largest homeless populations in the United States, I’m constantly being confronted by signs of poverty. And it always bothers me. Not in a “get off my lawn” kind of way. But in a way that I feel overwhelmed by it. I hate seeing elderly homeless people. Where are their families? Why is there no one to take care of them? I guess I imagine they could be my grandpa and that makes me sad and worried for them. I know there are a million issues that go into why people are homeless and it’s such a difficult problem to tackle. But it genuinely shakes me every time I see someone who is obviously struggling. Like I can’t handle how vulnerable they are.

I was shooting (images for my upcoming book) in Palm Springs over the weekend, and I went to Trader Joe’s to grab flowers. There was a guy in front of me fussing with a coin purse, taking forever to check out. I wasn’t really paying attention, looking at my phone, trying to be patient and mind my own business after a super-long day, but I surmised that he had tried to use an EBT card and it didn’t work so was trying to pay with insufficient coins he had, but gave up when he realized he didn’t have even close to enough to cover it. He left the store before I really realized what was going on. But later I was overwhelmed with guilt about not doing anything. It was probably like $17 worth of food (bread, cheese, etc) and it would have been nothing for me to have just said “hey can I pay for that?” The manager had to come put all his items back, which he announced after ringing that super-loud Trader Joe’s bell.

I keep having experiences like this in the store. Someone not being able to pay for what they have or coming up short. I saw a man at the store last night come in to get a cash redemption for $0.05, guessing he was just trying to collect money from turning in recycling items (a totally honorable way to make money imho). I’m not narcissistic enough to believe all these things are happening to teach me a lesson, but these experiences have been a gentle reminder to keep my own financial anxieties in check, to feel gratitude for what I have and the privileges I’ve been afforded. I worry about money every single minute, but my worries are trivial compared to what many people are dealing with.

Being in a financially tenuous situation has reminded me of my own tendency to only look up, to not appreciate what I have, to feel sorry for myself instead of thankful, and to compare myself only to people who have more. I think I get this from my parents, who always seemed to notice how much more money their friends had instead of noticing how nice their lives were. It wasn’t until college, when I went away to a school filled with affluent students, that I realized I’d also had an affluent upbringing, filled with the types of activities and experiences not everyone had.

At this point, you’re probably reading this wondering what the hell any of this has to do with dating. Here’s what. I think there’s a lot of “looking up” going on in the dating world. I don’t think it’s always bad, but it can make things weird.

I have a friend who has a terrible pattern for falling in love with Instagram hotties. For him, Instagram is a dating app. Like he actually meets people on it. He’s constantly being like “check out this guy I met on Instagram, we’re going on a date next week.” And it’s always the same kind of guy. It’s always a guy with a perfect body with over 20k followers who posts only shirtless selfies. Announcement to everyone: the type of guys that post shirtless selfies make terrible boyfriends because their thirst for attention never subsides and cannot be fulfilled by one person. That’s a vast generalization, I know. But a shirtless selfie does nothing but ask the question “validate me?” All social media posts seek some type of validation, but the shirtless selfie holds a special, insidious place on the spectrum of harmful, body-dysmorphia promoting, superficial nonsense gay guys can fall prey to.

ANYHOOOOOO, this friend of mine also posts a ton of shirtless selfies and completely misrepresents what he actually looks like on his own Instagram account. He contorts his body into positions that make him look way more ripped and in shape than he is. And this gains him entrance into the world of Instagram-Ken-Dolls he so admires. But none of his dates ever go anywhere, because he’s always trying to hook up with someone even hotter than the one before. He’s always looking up.

I’m not saying you shouldn’t seek out people you’re attracted to. I guess what I’m saying is to be aware of the things that are drawing you to people. Do they represent something that you see lacking in yourself? Also, are they so involved in looking up that they’ll never be satisfied with the person in front of them. I’ve only really dated in New York and Los Angeles, and I always had the sense in both cities that people have a hard time settling down because there are, at all times, a million better options than the person you’re with. It’s hard to be satisfied. In Los Angeles, there will always be someone hotter than you because everyone here looks like a model. In New York, there’s always someone with more family money because no young person that lives there does so without family assistance.

The point of all this is that you are somebody’s UP. It’s important to keep this in mind and to be grateful for it. It’s also important to remember there is no true up and down. Someone you might think is the smartest, hottest person on earth may seem totally unattractive and idiotic to someone else (I’ve been experiencing this a lot lately when I show my friends pics of guys I’m obsessed with and they’re like “EW”). The other lesson is to truly give people a chance, even if you think they’re above or below you intellectually, emotionally, or physically.

I’m constantly thinking people are out of my league. Like too cool or too smart or too cute for to go on a date with me. This is the downside of looking up. Believing that there actually is an up. In the dating world there isn’t really. People are attracted to people for different reasons. Obviously smarts and physicality play a big role, but other innate factors play into it as well. The lesson I’ve learned over the past few months is to be thankful for what I have. Regardless of how freaked out I am about money, I have, at least for now, a really nice life filled with great experiences. And in terms of dating, I may feel constantly out of my league but I’m also realizing leagues are stupid. I’ve got some fun things to offer. Maybe I’m your up. Maybe you’re mine. WHO KNOWS.

A recently-single friend of mine noticed a trend on dates he’d been going on. He’d go on one date and then never hear from the guy again. He’s a smart, cute guy with a great job, so he seems like he’d be a great partner. However, he’s been going on date after date with guys who want to meet up and then never talk again. I’ve actually had this experience too. Like people just want to meet you and then never talk to you again. Is it that the social media version of who we are is inherently better than the real life version? IS IT OUR GAY VOICES? What is it? I think this ghosting pattern is pretty normal these days.

My genius assistant Jess pointed out that we live in the age of comparison. More information about us, more imagery is being shared than ever before. There’s more to compare and rank. And this can lead to a dating world where no one is satisfied because everyone is constantly looking for someone better who doesn’t really exist (because only the idea of that person exists, the version of them sold by their online persona). We’ve got to find the mid-point between completely undervaluing ourselves and just dating the first person that comes along and being so selective that no one is satisfied ever. We’ve got to stop looking up and start looking out.



17 thoughts on “Dating Sucks: Everyone Is Looking Up

  1. I love this and needed to hear it today. As a small town girl (Colorado mountain town) in the big city (chicago) I tend to put on blinders to a lot of poverty. We are currently house hunting and I have spent the day pouting that my “dream house” was sold before I ever even got to go inside, that I’m having to compromise on size and location. Clearly these are problems that lots of people would love to have. An reminder to be greatful, kind and generous totally hit home. Thank you for all of your recent posts.

  2. Orlando, I can’t give you any dating advice but I do know that you end up meeting your partner when you least expect it. It seems that looking for someone never works. Put your phone down! Try to enjoy your singleness & let whatever happens happen.
    You are a wonderful writer. Your communication skills & the way you see life are going to make you a great catch for someone. Hang in there.

  3. Oh Orlando! You’re such a great catch? Someone lucky enough will find you. 🙂 Just take your time and enjoy your life.

  4. Yes! This is all on point. We really do live at such an odd time: so much “curation” & connectedness, but so much loneliness. You are a kind, sensitive soul, Orlando, and I think life is sometimes harder (but richer) when you can see and identify these things about the human experience.

    Keep doing what you’re doing with design, writing and all the rest of it. I’m rooting for you.

    1. My daughter just listened to this podcast and recommended it to me also! She’s a regular listener (and economics student), but thought it was particularly interesting for most people.

  5. It’s okay to feel sorry for yourself and struggle even knowing that others have it worse. You’re helping yourself now and will have plenty of opportunity to help others once you have healed and things are going well for you. I have no doubt you will continue to be inspiring to yourself and others and will find a partner who will appreciate that you are introspective as well as ready to start looking out. xo

  6. I love that if you’d realized what was happening that you would have paid for the man’s groceries at TJs. I echo the “put down the phone” comment. And I appreciate your reinforcement of my ban on Instagram for my 13 year old daughter.

  7. “However, he’s been going on date after date with guys who want to meet up and then never talk again. I’ve actually had this experience too. Like people just want to meet you and then never talk to you again.” It’s like that everywhere. Not just in LA or NYC. It’s the same thing in every big city. I always thought “not wanting to talk to you again” meant only one thing: they were just not that attracted to you. But then I read this relationship article one day which made the point that there are people out there, which are only in search of “sexual validation” and nothing else. The gay guy in search of sexual validation is the type of guy who always needs to be reminded that he is (sexually) attractive. It’s not enough to have only one person do that for him. He craves the attention and adulation of as many men as possible. It’s a huge self-esteem boost. This makes sense. Knowing 50 different men find you attractive is better than just 5, so I get it. This need, however, to be validated all the time gets addictive, and impairs one’s ability to date or commit. This is one reason why oftentimes you never hear back from the guy you met last night. It’s not that he did not like you. It’s just that he’s now busy getting compliments from someone new, but that person will become “old” soon too. A few more reasons for rejection. The guy does not appreciate your intelligence or maybe even sense of humor. He simply does not care about those things and may even, secretly, find them irritating. I’ve met quite a few such guys. What else did they have in common? They were all very attractive. I’ve come to the conclusion that in the gay community there is often an inverse correlation between physical attractiveness and intelligence. The more attractive the guy is, the less likely it is he is funny, smart, amusing, etc etc. So next time you meet a guy who’s, say, super cute, don’t be surprised if a) he is dull as dishwater or totally unfunny and b) you never hear from him again. So it’s up to you to choose what you value more: looks or anything else (e.g. intelligence, humor, kindness, etc). I’d say that it is rare, not impossible, to meet a gay guy who embodies it all: attractiveness, kindness, intelligence, humor, etc. etc. Last, but not least, we have the comparison thing, which you mentioned. In a digital world, we have a culture of oversharing, mostly oversharing of images. This is the selfie culture, and it is not going away anytime soon. So it’s quite natural, actually, that you will be compared to others. I’m not sure there’s anything wrong with that. The real problem is that many gays make a hobby out of it. It’s ok to compare someone to two or three other people, but when you start comparing them to even more people, it gets crazy. You become like one of those people who are addicted to coupons or discounts, constantly price comparing and trying to save even more money. Unfortunately, apps like Grindr, Scruff and even Tinder encourage folks to do exactly that: compare people constantly, hold out for some new possibility, question their current choices, look for the next best looking person (and there will always be one), etc, etc. It’s a very sad state of affairs. Call me old fashioned (I’m in my mid 30’s, not that old) but I wish I could go back to a time when people used to date differently.

  8. I used to be an avid reader of your blog, until I noticed that the content was not being updated, quite so often. Like most of your readers, I think it was hard to read the reality of your situation but can appreciate your openness and willingness to express your vulnerability. I too went/am going through a separation/breakup, after 12 years together (I’m only 32, which makes this real tough) I found us growing apart. I am now going through much of the same things you are going through, with the exception of deciding when/how to sell our condo (purchased only 2 years ago, thinking we would own it forever), whether or not we should just separate or completely divorce. At 32 I never thought I would be entering the dating world, especially a world with smartphones and dating apps. I don’t think I’m really thinking about dating at this point, just trying to keep my head above water and make it through my work day, everyday. I guess I don’t know where this is going but a number of things in this post made me stop and realize I wasn’t alone in many of my feelings and thoughts on social media. I guess I just wanted to say thank you for your honesty, it has been helping me change my perspective on my situation and look ahead, knowing that we are all just trying to do our best.

  9. I find myself checking out your blog more often these days. While I’ve always found you to be hilarious and talented, I’m drawn to the vulnerable honesty you’ve been dealing lately. There is nothing that makes me feel more guilty for whining than someone who points out that I have a roof over my head and food in my fridge. And let me tell you, I AM so very grateful for all the fantastic in my life. But, I also think it’s totally ok to sometimes feel gross, sad, tiny and overwhelmed, despite good fortune.


  10. I second what Mikey says! I originally came for the design talk, but I’m so impressed by how beautifully and insightfully you write about your experiences. Thank you for being so honest.

  11. This is probably the worst idea I’ve ever had, but I so want to set you up with a friend of mine.

  12. you know what? the same thing is happening to lots of parents these days, trying desperately to show how their kids are cute, smart, have the best grades, play all the instruments and are so great in sports. I am so tired of these “looking up” behavior. That great kids of my friends are worse than the shirtless guys LOL

  13. Be yourself 100% and focus on that. Then at some point when you meet someone with whom you click, they will like YOU and support who YOU are, and you won’t have to throw away your ugly sandals (see I read earlier posts). Also, try reading, if you don’t already. It’s a really great blog about acceptance, letting go of the past, being mindful, focusing, etc. And you don’t have to join his programs or video courses to read the blog. I’m fairly certain he’s written several posts on comparing yourself to others. You are an interesting person and a talented designer. Glad I found YOUR blog.

  14. It is also hard for a family member to lose the friendship/close relationship they had with your partner in a NY minute.

  15. “I’m not narcissistic enough to believe all these things are happening to teach me a lesson”. I’m appreciative that you’re a maker, in a seemingly shallow environment, yet you have this depth and platform. I also want to tell you to not beat yourself too bad for the EBT scenario, as a social worker I can attest that while it’s embarrassing, I’m impressed and inspired by my clients tenacity and willingness to make things happen.

    I also love your writing.. and your mama’s comments.

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