Dating Sucks: Which App is Applicable?

Editor’s Note: To those of you who read my post last week about my breakup, the change in tone here might feel a little jarring. I actually wrote that post over a month ago, and I’m doing a lot better than I expected. There are a lot of tumultuous things going on in my life (some I can’t mention here yet) so I’ve been in a state of rediscovering my goals, both professional and personal. One of those goals is and always has been to communicate with people (THIS MEANS YOU) so the tone of this blog, while staying in the interiors/lifestyle realm, is going to shift a bit towards things I’m currently interested in, including love, dating, and relationships. This series, “Dating Sucks” will be an ongoing diary of my experiences dating as well as a place to talk about issues that relate specifically to dating for gay men as well as issues that are more universal. If this isn’t your cup of tea, skip and move onto the next design post. However, I think relationships (with family, friends, and lovers – LOL I hate that word) are important and fascinating to explore. This is a change I’ve been meaning to make for years, which is why I redesigned the site (with help from the lovely people at Dash Creative Group) to include the Art, Decor, Life, and Style categories. Enjoy!

Dear Dating Diary,

After my recent breakup, I said I wasn’t going to date for a year. But a bit over a month into my singledom, still reeling from the rejection, I started to feel like the dating boycott was making me feel even more invisible than I already felt. I was dumped, essentially, for being fat and gross and my already shaky self-esteem took a nosedive. So I decided to join a few dating apps and see if I still registered on the spectrum of “not too disgusting to have a drink with.”

I joined OKCupid and Tinder. I can’t get down with Grindr or Scruff or any of that nonsense. I’ve been on Grindr (between my last two relationships) and my memories of it are akin to those dreams I used to have in high school where I came to school naked and everyone laughed at me and then I burst into flames. Those apps are so incredibly transactional and aggressive, and while I’m sure the users are actual human beings with souls, they don’t seem to want to show it. Not for me, Grindr/Scruff. NO MA’AM! I AM A HUMAN WITH A HEART AND A MIND AND I WANT LOVE.

There’s something unnerving about all these dating sites/apps/tools, even the wholesome ones like OKCupid and Tinder. The other night, I was simultaneously shopping the sale section on Urban Outfitters and scrolling through profiles on OKCupid. The interface was essentially the same, a grid of appealing (and unappealing) images asking, “U WANT THIS?” Obviously, there’s something good about these sites – they introduce you to people you might not otherwise meet. And they let you know that guy you’ve always thought was cute is single. But I can’t shake the feeling that there’s something kind of strange about the time we’re living in, where we can literally shop through a catalogue of men, trying to decipher which one you might like to procure.

A few things struck me about the profiles on OKCupid. First, there are still guys out there using that tired-ass “masc for masc” language. For those of you who don’t know what this is, it’s basically a guy who states clearly in his dating profile that he wants to date only masculine, straight-acting men. It’s a throwback to more oppressive times and it’s frankly tired and pathetic. What bothers me most isn’t how stupid I think that is, but how dated. Writing that these days just makes you sound old. In a bad way.

Speaking of old, I’ve decided I hate young people. All these sites ask you to give an age range (mine is 30-45). I just can’t with people in their twenties anymore. My generation, the earliest of millennials, knew stuff about previous generations, about the 60s, 70s, 80s, etc. We were fascinated by the music and art of past generations. The super young today are idiots. They’re all “WHAT’Z A CD???” Learn some 90s history you freaks. I basically just wrote this paragraph to talk shit about young people because I hate them and they deserve it, but I digress (Sidenote: I’m sure if you’re a young person reading this, you know what a CD is and I respect you).

While it’s difficult to wade through all the self-hating messes on OKCupid, Tinder comes with its own set of issues. Mainly that I get addicted to swiping. For anyone who doesn’t have this app here’s how it works: the app geolocates you, finds potential matches, and you swipe left or right depending on if you like or dislike them (yes, it’s that harsh). But once I found out that you can get to the end of a list (like the app runs out of people for you to swipe yes or no to) there’s just a blank screen. I find myself swiping as fast as I can so I can get to the blank screen and know that I did the whole assignment. The overachiever in me just wants to get an A on this assignment that no one asked me to do.

Is there something disgusting, demeaning, and world-ruining about swiping someone away just because you hate their ugly face? Absolutely. Is it fun? One. Hundred. Percent. Apparently, the new dating world is designed by assholes, for assholes. And I’m a complete asshole, because I’m totally participating in it.

But wait, it gets totally grosser. Feeling like I might have better luck finding quality matches on a more elite site, I applied to join both Raya (a dating site for Insta celebs and wannabes) and TheLeague. Raya was sold to me as a place where beautiful influencer/artist/celeb types go to “network.” I was all “that sounds cool” and applied. They rejected me. I’d be nonplussed by this if I didn’t know so many garbagepeople who are on it. But I didn’t really care, none of these sites are going to make or break my dating life (unless of course my future husband is on Raya. PLEASE DON’T BE ON RAYA, FUTURE HUSBAND!).

TheLeague turned out to be a massive disappointment. It was sold to me as solely for Ivy League graduates (which I happen to be, with degrees from the two worst Ivies) but when I got on there most people were not graduates of the eight schools that make up the Ivy League. To be honest, I think the Ivy League is stupid. But if you’re going to have a dumb app that’s trying to be elitist, MAKE IT ACTUALLY ELITIST. Know you’re audience! If I wanted to be matched with randos who went to Rancho Cucamonga Hotel School for Dogs, I’d stay on Tinder.

I have a theory about online dating. Once you’ve been matched, you have to ask a guy out pretty quick, like within a week. Otherwise it devolves into this thing where you just end up chatting forever and ever and never meet up. Some people just use these sites/apps to entertain themselves. Or just to talk to strangers with no strings. During my last breakup, when I was a total mess, I used them just to learn about people. It made me feel hopeful that there were still people out there to meet, still connections to be made. But chatting with no intention of ever meeting up is kind of a crappy thing to do, because the purpose of these tools is to go on actual dates.

I’ve had pretty good luck getting dates so far (I’ve been on five, to varying degrees of success) which has been kind of surprising and reassuring at the same time. I have absolutely no confidence in my appearance, never have. But getting dates has made me think, “maybe I’m not a complete rotting-ladyface-witch!” The dates have all been really nice. It’s this weird, repetitious pattern of interviewing people about their pasts and trying to turn your life story into short enough sound bites that they don’t get bored.

Since you didn’t ask, a quick dating tip, which I was reminded of on a recent date: Don’t talk too much. I went on a date with this guy (who I knew in real life then matched with on Tinder) and he literally didn’t shut up the whole time. Like I’d ask him a question and he’d just go on and on. The way a normal conversation works is that if someone asks you a question, you reciprocate eventually with a question. This guy literally never asked me a question. I think maybe he was nervous, not wanting there to be silence. But my go-to for this has always been to ask a question. It’s a psychological fact that the more people talk, the more they enjoy the conversation. Keep this in mind on your next date and just ask a million questions and let your date talk. He’ll leave thinking he had the best conversation ever and you’ll leave knowing you “won” the date.

Yes, you can “win” at dates. I told my friend this recently and he hung up on me for saying something so gross. But the goal of the date is to make the other person like you more than you like him. If you do this, you win. If you do not, YOU ARE THE WEAKEST LINK. There can be no ties. Nothing is mutual. The world is a terrible, cruel, and meaningless place.

I’ve been enjoying dating and staving off depression by working out a ton (I lost 20 lbs!) and taking a ton of supplements (fish oil, St. John’s Wort, glucosamine, etc, I have a whole gag-inducing regimen of horse pills I take every day that is making me feel much better/healthier/like I’m going to vom). And dating has been a fun exercise. I guess I consider the dating apps to be necessary evil, a way to connect with other guys that are actively seeking a relationship. I’m doing my best to be kind and responsible (no ghosting) and as open as I can be. I’m going to keep documenting this because dating, love, and relationships relate directly with domesticity and the theme of this blog. So keep coming back for more posts on why DATING SUCKS.


25 thoughts on “Dating Sucks: Which App is Applicable?

  1. I’m a little confused by the self hate. You are one of those guys that women are sad that are gay because you are super hunky. Some people are just butt holes and others are just not a good match no matter how nice. There is a man out there for you. I’m sure you have plenty of readers that would love to date you but are just too nervous to ask you out. PS, you’re hilarious and make me laugh every time you post.

    1. I totally agree! As a straight woman, I can vouch for the fact that Orlando is super hunky, smart, talented, etc.! There is no reason for self hate, whatsoever…

    2. Another just a girl here who thinks your hot! And hilarious, and talented. You’re already a winner!!

    3. Another of the legions. Orlando you are HOT.

      As for dating apps, I tried a bunch and had the most success with Bumble… success as in I found my husband. I couldn’t get down with tinder or OK cupid because of the horror stories of disgusting comes on I’d heard from friends. Anyways, I was curious if the Bumble model worked for gay men (i think it does?) and came across this article:

      Chappy! May be worth a spin if you haven’t already. I know you love a good pun.

  2. Whyyyyyy with the online dating? Skip the arbitrary year of singledom, sure, but there is no need to force anything with apps. Live your life: go out with friends, read books, try new hobbies, travel. If any of these things lead to romance, wonderful. If not, you are still a better person for your experiences and what you learned along the way.

    The key to a great relationship is finding someone who loves the REAL you and pushes you to become a better version of yourself. Dating apps are the opposite of that: fitting yourself into a fake “fantasy of a perfect person” box in an attempt to get someone to like you.

    And don’t say “Don’t worry, I’m just having fun, not looking for anything serious,” because that is the easiest way to accidentally get into a terrible relationship with someone for YEARS, because you didn’t look at that person very critically at first, but after a while it’s more comfortable to just stay together than venture out into singleness again. I can’t tell you how many of my friends are in sad long-term relationships with people that mean nothing to them who started out saying “we’re just having fun.”

    Sorry to be a random stranger on the Internet giving you a lecture. I just get very sad when good people don’t take the time to understand themselves and their own worth. Choose to put yourself first. Choose to have high standards. Choose to live a full life!

    1. As someone whose breakup nearly exactly paralleled yours – with the added exception that after living together for a month after breaking up, he got married shortly after (!!!) and ultimately left civilization to live in a “yurt-stead” near the Appalachians (shit you not) – I fully support this advise. I started that relationship as something I wasn’t too critical of, and then you get the inertia of the next step, so on…

      While I was single afterward, I did what Anon suggested. Lots of hiking (in Sonoma County, no less) and time with friends, spreading out the energy invested in that one relationship with others. I also feel like that time allowed me to “bomb proof” my life a little – time invested in figuring out how to better manage stress, define where my barriers are, invest in other relationship in my life. Long story short, take care of yourself and a number of things may fall into place in ways you don’t expect 🙂

      PS: You don’t have a rotting-ladyface-witch face.

  3. Maybe instead of jumping intentionally into dating so soon (if you meet someone IRL, that’s different, but the apps are intentionally putting yourself out there), perhaps you should consider some therapy for your self-image? I went through two years of therapy, even when I didn’t have serious issues, and it made my relationships so much better. I just wanted a “tune up,” so to speak, because I could tell things would eventually get bad if I didn’t address minor issues immediately. If you know you struggle with your body image and self esteem, the sooner you start the sooner you’ll begin to feel better.

    It just sounds to me like instead of finding another man, you need to let yourself heal. Take care of yourself, even if you decide not to take this advice.

  4. Oh Orlando, I agree with Jamie Rowe (above) – you are super hot! And you’re funny and a good writer and a great designer. Basically, you’re awesome! I hope you win all the dates.

  5. Hi Orlando, I follow you on IG and just read your posts for the very first time… this one and the one about your breakup. What a lovely writing. I know it must’ve been so hard to share something like this, feeling vulnerable, but I truly believe (and I think you do too) that you’ll get past this stage and you’ll come out even stronger! You’re one talented, BEAUTIFUL man, so don’t let your ex-boyfriend feel like you’re anything less than that. I believe in karma: no one should ever treat the person he/she’s ever loved like that.

    Anyway, I agree with fellow readers that you need to do YOU. You’ve been in two relationships back and back and I know other friends who are chronic daters.. they just can’t seem to be alone. Forget Tinder and other dating apps. Take at least six months, maybe even a year, to focus on you, family, friends, hobbies, group activities, taking cooking classes, etc. Love will come to you when you’re ready, and I don’t think you’re ready yet, emotionally and mentally. You need to realize your worth, because you sound like you’re very hard on yourself.

    I look forward to more posts about your life! Please keep us updated xo

  6. Do not date right now! Especially when you appear to be super vulnerable!!! In agreement with the others! It has disaster written all over it!

  7. Orlando, you are super funny! I loved reading this post and can vouch that online dating can work. I met my guy on Bumble and we’ve been together for 8 months. That’s not super long, I know, but we’ve been pretty much inseparable since a month into meeting in person. I didn’t expect to meet anyone, just signed up as a lark but it was totally fun getting to know ppl without any of the risk. I asked a million questions and found a few really interesting people, people I would have never met otherwise. Anyhow, you’re cute, smart and funny, a total catch! I hope you win all your dates and I agree, no ghosting!

  8. Maybe it’s just my imagination, but I think not: this is the first post in awhile that you sound like you. (Or at least, the version of you when I first read your blog. I’m sure you have several versions of you. Don’t we all.) Don’t get me wrong, I loved reading about Orcando and followed every step, but your voice was subdued. As I write this, I sound stalker-ish and weird, so maybe it is my imagination after all…

    Anyway! Great post. Welcome back to the land of the living. Good luck dating, what a zoo. And for what it’s worth, we’ve all taken a vote and decided that you’re totally hot. I wish you could see it, but self-image is a bitch, so no judgment.

  9. You’re always so hard on yourself! You ooze super talent in all ways, someone needs to give you a bone crushing 10 minute hug!

  10. I used to just hate dating apps – so superficial, why do you hate my face? you haven’t seen how cute my heart is, etc – but then I thought, back in the olden days (2001?) you’d go out with someone after meeting them at school/extra-curriculars/volunteer/mutual friends/work/bar and you sure as heck wouldn’t say yes please if you thought they had an ugly face…no matter how cute their heart was (sad but true). So really, isn’t swiping right (left? haven’t used tinder) the modern day buying a cutie a drink at the bar?
    You do you! Hope you’re having fun on the dates.

  11. I recently (well, 9 months ago…) went through a horrific, traumatic breakup so I completely understand everything you’re saying. Deciding when to start dating again after a breakup is such a personal choice. Everyone grieves differently, so I think that if you feel that you’re ready to date, which you clearly do, then that’s great! It’s nice to be validated even if it just for your looks, because I know the self-loathing that presents itself after you’ve been dumped. It’s awful. I pretty much avoided mirrors for like 5 months after my breakup because I would just see an unloveable monster staring back at me and every morning I would think, “who will ever love this again?” while slapping makeup on my stressed and tired skin so I would look more alive than dead. I don’t really have anything constructive to add. It’s just reassuring to read something that makes me feel less alone. I’m excited to follow this series!

  12. ive always enjoyed your witty writing. i hope you can find the fun in dating [i met my love at 19 and i wish i wouldve whored myself out a bit more beforehand]. so be a whore and an app using asshole. revel in it. and stop being so hard on yourself. you’re fucking awesome.

  13. Omg you touched on so much stuff that I want to comment on!

    I started to read the comments but got bored. Not everyone is as clever as you (us) but maybe one day they will be. Confidence and self esteem is a roller coaster and I don’t think you should feel bad for doubting yourself or feeling trash when that’s normal and healthy. And really I can’t speculate on what’s healthy but dismissing your self doubt by saying you shouldn’t have it seems unhelpful. You’re obviously hot and I’m SHOCKED raya didn’t approve you when I know someone on there that isn’t near as “famous” as you. She is a Femme Cis female so maybe that’s more in demand?

    Anyhooooooo when I moved from Orlando (hey that’s you!) to NYC I was still on OkCupid (tinder wasn’t a thing yet) and being somewhere more populated and dating a lot of guys, some really superficially hot, helped me feel better about myself a LOT. I think this coupled with turning 30 really helped me reach a stride in me confidence. I think people in their 20s are obnoxious because they’re really in their head about everything and what people think but at the same time know it alls. I’m very guilty of this too!

    I really miss the excitement of being single and I hope you enjoy it more this time around. Enjoy your freedom. Travel or relocate for a little bit or something. Do something you couldn’t do with some dummy in tow. Or don’t. Have fun!

  14. I LOVE your writing and again for the record you are a handsome devil and some wonderful guy is out there for you. I tell myself that all the time 🙂

  15. Orlando, I just wanted to chime in to say it’s so surprising to hear that you lack confidence in the looks department, because you are SO attractive. It makes me sad that the pressure of the society we live in can cause such insecurity in so many people. You’re the kind of person I look at and think, “He’s so smart, funny, AND good looking.” I’m genuinely sorry you had to go throw this recent breakup–I followed your Orcondo posts on Emily Henderson and always enjoyed your voice and of course your massive design TALENT. Dude, you have all the goods. You are awesome. Thank you for your honesty and openness. I wish you the best and will follow along here. 🙂 xox

  16. excuse me you got dumped for what? being fat and gross? then that guy didn’t deserve you. body shaming in the gay community is terrible and paralyzing, many people struggle with their bodies (I do) – but when we keep hitting that wall of perfection that keeps getting higher – we hurt ourselves in the long run. However, that wall of perfection will usually have a door and that door leads to a bakery where I would rather sit and eat croissants with jam while I checking people out as they deadlift. I mean, how satisfying would it be to eat cake outside the window of the Equinox in WeHo? That sounds like a great first date to me.

    As for being gross, humor is subjective (I assume we are talking about humor, unless we are talking about gross fetishes – that’s even more subjective). You want someone to laugh with you not at you, isn’t that the point in relationships? To find joy and laughter?

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