Dating Sucks: Wait, Is This a Date?

Photograph by Zeke Ruelas (an outtake from “Get it Together,” available now for pre-order)

Editor’s Note: I love this image by Zeke Ruelas. It was taken for a chapter from Get It Together about weight loss and body dysmorphia. I know I look absolutely insane but it makes me laugh so hard. Okay bye.

Dear Dating Diary,

The other night, I went to dinner with a guy I’ve been “hanging out” with. I say “hanging out” because I have no idea whether the two times we’ve hung out were actual dates or if they were networking. The first time we hung out I texted all of my friends and was like “IS THIS A DATE?” I got mixed responses. We were going to dinner, so that made it kind of datey. But he also works in my field, so I thought maybe he just wanted to meet and chat about work. Honestly, both would have been fine but the ambiguity is what drove me crazy. WHAT ARE WE DOING HERE AM I SUPPOSED TO BE FLIRTING?

One of the weird things about being gay is that the same people who are your friends are also people you could potentially date. This always confuses straight people because they’re like “WHY DON’T YOU DATE KEN HE’S HOT AND YOU GET ALONG!” And you’re like “EW NO HE’S MY FRIEND THAT’S LIKE DATING MY BROTHER!” We somehow create these little walls between ourselves once we become friends that prevent us from seeing each other as potential romantic partners. I don’t really know why this is. DO STRAIGHT PEOPLE DO THIS?

An added layer to this “we’re friends/not potential mates” wall that can arise between gay friends is that it kind of makes you feel like you have to jump on a romantic relationship with a new person before you turn into friends and any chance of that happening are erased. Like it stresses you out a bit because if you like someone then you have to make them your boyfriend immediately before they relegate you to the role of “friend.” It’s an added layer of pressure that can be anxiety-inducing.

This guy. I’m gonna call him Brandon because that’s one of my favorite go-to white boy names. I use it sometimes when I order coffee just to laugh at how funny it would be if my name were Brandon in real life. Like how different would my life be if I didn’t have this weird-ass name? Anyway, Brandon and I have been Facebook friends for a long time. I don’t really know how we connected but we saw each other at the gym a while back and were like “LET’S HANG OUT.” But he had a boyfriend at the time so the premise of that previously-discussed hangout was obviously platonic. But then he texted out of the blue a while ago (after breaking up with his boyfriend) and was like “let’s meet up!” and I was like “Duh you’re gorgeous let’s hang.”

I’ve had a crush on this guy for a while so I was excited to hang with him. But strangely I’m not that desperate right now. Like I guess I’m not actively seeking a boyfriend because I’ve noticed how much better I am on my own (for the time being). When I’m in a relationship I tend to dissolve into it. I fade into the minutiae of daily life with a boyfriend, like grocery shopping, what we’re going to do for dinner, planning the weekend, etc. It’s nice, because it’s constant companionship and affection. But it’s also draining and makes me boring. I have less to write about because the only thing I really care about is my boyfriend and that’s boring and unrelatable. Realizing this has been a good thing in that I don’t feel like there’s some hole in my life that needs to be filled.

Knowing this didn’t stop me from being very nervous on my first date (was it a date?) with Brandon. We went to a decent restaurant in Beverly Hills and chatted about our lives and goals. It was typical first date type conversation. I’m pretty good at dates because I know that the key to them is asking a lot of questions and getting the guy to talk about himself. This works because the majority of humans are egomaniacs who only want to talk about themselves all the time. So they’ll feel like it was a good date if they got to talk a lot. It’s a scientific fact. The conversation was decent. Not my best work but passable.

A huge moment of anxiety came at the end of the night when he dropped me off because I was like “AM I SUPPOSED TO TRY TO KISS HIM I CAN’T TELL IF THIS IS A DATE!” We ended up having a super awkward kind-of-on-the-lips-kind-of-on-the-cheek kiss that makes me laugh to think about. It’s so funny to me how awkward it was. It’s like if my self-esteem could be boiled down into one action it would be that one very awkward non-kiss. As you can probably guess, I’m not very aggressive and I never want to push myself on anyone. I’m like the opposite of a #metoo moment. I got out of the car and was like, I STILL HAVE NO IDEA WHETHER THAT WAS A DATE OR NOT.

As I walked inside I was pretty resigned to the fact that I’d never see Brandon again. I was sort of disappointed but mostly I didn’t care. Again, I’m kind of feeling like it’s okay to just explore and meet new people without any sort of expectations aside from just wanting to learn more about them. The only thing that really bothered me was that I was nervous and maybe acted like a nerd. Brandon is hot and perfect looking and whenever I go on dates (WAS IT A DATE?) with guys like that it brings out the most in my body dysmorphic/I hate myself vibes. I was feeling intimidated and out of my league.

You can imagine my shock and excitement when Brandon said he wanted to hang out again. I was like WAIT MAYBE THAT WAS A DATE??? We made plans to hang out Friday night and I didn’t hear from him until Friday about what he wanted to do. He ended up bringing me with him to a dinner party his friends were hosting. We were the only ones not drinking. I’m not drinking right now, mostly for superficial reasons but also because it’s helping me be way more energetic and because it helped me heal from being totally depressed last year.

After dinner (which was delicious, his friend is an amazing chef) we went into the living room where everyone continued drinking wine and Brandon and I continued drinking sparkling water like dorks. After a few delectable glasses of wine, the host of the party turned to us and was like “ARE YOU GUYS ON A DATE?” I must have turned bright red because I was MORTIFIED. I think my response was “I DON’T KNOW, MAYBE?” And Brandon didn’t say anything. Then the host was like “ARE YOU GUYS GOING TO HOOK UP?” I was dying inside, but also thought this was the most deliciously uncomforable thing that ever happened in my life. Again, Brandon said nothing and I said, “MAYBE?” There was literally no “right” thing to say.

The drive home, like much of the evening, was awkward. I asked Brandon what he thought about the host asking us if we were on a date and he said “I just thought it would be nice to hang out and see what developed.” That was probably the smartest thing to say, because anything more intense would make him sound needy, anything less committal would make him sound mean. At this point I confessed that I’d had a crush on him for a while (because HEY WHY NOT WE ONLY LIVE ONCE). We went to my place, hung out for a bit, and NOTHING HAPPENED (aside from a small lips kiss on his way out, which was nice).

I’m not sure if I’ll ever hang out with Brandon again which is fine. He’s a sweet, special guy but I’m strangely not feeling that vulnerable about it. Obviously, he’s cute and fun so I want to see him again. But my whole outlook right now is that I’m having fun meeting new people and learning about them. I don’t feel an intense need to jump into anything. Obviously, if I fell in love with someone that would be a different story. But for now I’m good just exploring and seeing what happens.

BUT CAN WE JUST ALL ADMIT THAT THIS WHOLE THING WAS SOOOOO AWKWARD AND CONFUSING? Being gay is annoying sometimes. Now, if you’ll excuse me, I’m going to sit here contemplating whether either of those interactions can be classified as “dates.” I honestly may never know…









41 thoughts on “Dating Sucks: Wait, Is This a Date?

  1. Ugh. Dating is the worst! I have a lot of dude friends (I’m a lady) and people used to always say, why don’t you date so and so, and then I’d throw up in my mouth a little because, gross, so and so is my friend! Now of course they are all married and I’m single, so maybe I should have rethought that?

  2. As a straight, married female, I keep encountering other women who will not let their husbands/male partners be friends with other females. Is this something that occurs in gay relationships, as well? Like, you’re in a committed relationship and your partner won’t allow you to be friends with men because every male friend is a potential affair? Or is this just an epidemic only affecting straight white women? It’s so annoying. Love your stories.

  3. It sounds like Brandon can handle a little razzing from his friends which is a good sign. I could totally feel all the awkwardness of dating (or maybe not dating) in this post. It’s really great how comfortable your feeling about taking your time and just being you!!

  4. Orlando,

    Two things:
    1. I had exclusively man friends for a really long time, mostly because I hadn’t seen enough Gossip Girl/Sex and the City/Friends (which has since been remedied). But I couldn’t get a date for years, because I was everyone’s buddy, and it sucked. Straight people do this too.

    2. I relate really hard to getting into a relationship and being boring! If you have any tips on not living for spending time with or getting approval from a SO.

    Best of luck! Hope Brandon figures out what he wants.

  5. I think women tend to decide men are brothers/friends only, much more than men do to women (in my experience even the “closest” of guy friends believe the door is at least a little open for dating, even if I would never even think of them that way.) but dating seriously is the worst. My now husband (well, by now I mean for the last 18 years and the only husband I’ve ever had. ? I just mean *now* as in he wasn’t at the time. ?) believed we were dating LONG before I knew, because he thought we were on dates, and I thought we were hanging out (because he never asked me on a “date” it would be us seeing each other at work and then going out afterwards to grab a bite, etc.) he eventually figured out I assumed a date was picking me up from my house, in which I dressed to go out, etc. and we had been “hanging out” for 2 months at that point.

    1. He might! But I try to be as fair and kind about guys I’m seeing as possible. There’s nothing really personal or demeaning about him here. I respect people’s right to privacy, hence the fake names (and often disguised careers, identifying characteristics).

      1. OMG, this is the first time I’ve noticed your “name” in a response here. I’m dying, that’s too funny.

  6. I love your stories and insights…humans can be complex. I always think it’s easier for different sexes and sexualities. But for any of us putting our feelings out there is scary, especially if you’re not even sure what those feelings are sometimes. Ugh, what can I say…enjoy the journey?? ? jk, journey…such an annoying term.

  7. I don’t see how anyone could be out of your league. You are very attractive and hilarious – the best combo.

  8. Forgive me for my glib response to what is, as usual, a vulnerable and insightful piece: That said, when I saw your title and photo, I was just like, “No, that is lettuce.”

  9. If his friends are throwing the party and asking the questions then he should be the one answering! Unless he was super nervous about upsetting you it was a bit of a dick move not to say anything and leave you to answer. He has a whole different dynamic with his friends than you do. Rude. A little like telling private jokes all night.

  10. “When I’m in a relationship I tend to dissolve into it.” Ugh. No sentence has ever described me in my current relationship more. And it’s not about him or the relationship. It’s me! I do this to myself! I have to actively force myself to break out of it and do other things that are for me, not for us.

    Seriously, even your throw away lines are relatable. I know that’s not what this post was about, but it totally got me. Thanks for being so brave and opening up to internet strangers about your feelings. It means a lot to me (and I’m assuming to many others) that you’re willing to be vulnerable and speak about the weird and wacky feelings stuff that most people keep to themselves.

  11. Maybe it was planned beforehand for his friend to ask that, so he could know your thoughts on the subject.

  12. That was not a date. Sorry. It was a hang-out, so there’s that.
    That “friend” is no friend putting both of you on the spot like that.UGH. Not cool or kind IMHO.

    When my daughter was a teen, I bought her the book, “He’s Just Not That Into You.” (my excuse? It was the 90s.)
    It is also misogynistic and silly to re-read now, BUT, the take away from that book was this:

    If the person you are “hanging out” with is crazy about you they will move heaven and earth to be with you.
    They will blow up your phone, they will make plans for next time before they leave from this time, and they will rearrange a schedule that is jam-packed JUST to be with you.

    I have lived this reality, trust me. I was widowed in my late 40s and went on to have had my share of hang-outs, is-this-a-date kinda things, and until I met my Chapter Two surfer computer geek now hubby, I had given up hope.

    I was fine alone, but when hubs and I met it was exactly like that stupid book -constant contact ( we lived in diff states back then) lots of future plans, a few good presents( my first gift was a fire engine red laptop! So silly flowers here, lol, lol)

    Your dude is out there. He just may not know it yet!
    Oh and in Feng Shui circles, if you put a horse figurine in the South this year you may see an uptick in romance!

    Wishing you cute dates that you never have to guess about.

  13. I did think it was a dick move to not answer when HIS friends were asking…I could never casually date because I agree with you, is it a date or not, there’s no in between. Glad you’re good with being by yourself and keeping your options open…you’re on the right path!

  14. Well, I have the perfect guy for you, even though he’s older and lives in Ireland. On the plus side, he’s in the arts and irons his sheets while on the bed and loves fine clothes. Perfect!

  15. Agree with the folk above – sounds like he’s currently “on a journey” if he doesn’t know what he wants, and so probably isn’t emotionally available at the moment. How long ago did he break up with his boyfriend?

  16. Yeah, I agree with the crowd. He sounds super wishy-washy, which in my experience equals death in the dating realm. Orlando you are (to my eyes) a nearly perfect human and you deserve WAY more than some flimsy corn husk of a dude who will blow away in a light wind.

  17. Hi, I think these were dates. Especially the 2nd one – you wouldn’t take a friend to a dinner party – you’d take a date. And I think the reason he didn’t answer the questions from him a friend is because he was scared you would say you are just hanging out, when he wanted it to be a date. Also I can’t believe you felt not good enough – you are good looking and funny and warm and talented. Is Brandon good enough for you??? Good luck xx

  18. In college (many years ago) I was hanging out in the suite of my dorm one night and talked with a guy on my floor late into the night. We did this a couple other nights and I heard he had a crush on me. I then was getting sleep deprived because I actually attended my classes and studied in college so I stopped hanging out in the suite. I figured if he really liked me he’d ask me out. I found out later he got mad at me because I stopped hanging out in the suite at night for a while and when I did again one night I talked about another guy who I had started dating because he had actually made his intentions known and asked me out. That was annoying and ridiculous of him if you ask me. So if you like him, maybe ask him out on an official date. It sounds like you made him aware you are interested. Anyway, the ambiguity can be annoying and I’d say don’t get too hung up on him. Doesn’t sound like you are. Good for you for being fine just being you. As for having to start dating someone before you can’t because you become just friends, isn’t that called the friend zone? I think in straight life guys get friend zoned more that girls.

  19. Agree with those above. If he’s not even willing to commit to the interaction being a date, he doesn’t deserve you, awesome Orlando Soria.

  20. If the kiss was awkward, the dinner was awkward, the drive was awkward…he’s totally nervous because he’s into you. You think he’s out of your league and he thinks you’re out of his. This is a nice thing at the start of a healthy relationship 🙂

  21. I love this post. Reminds me of when I started dating my husband. I swear we were “hanging out” awkwardly for about 2 months. We would do date like activities – bicycle rides down by the lake with milkshakes after, scrabble and dinner at someone’s house, brunch catch-ups, and night time hikes…. but he never made a move. We also worked in the same industry…. so I decided as he was new to the area, he just needed a friend. When he eventually did kiss me properly – I was so relieved that the mystery was solved. When we talked about it much later, he simply said “you were high risk”. We worked in the same industry, shared similar groups of friends … and he really really liked me. He just didn’t want to screw it up, and wanted to take the time to know me without the added pressure of being my “new boyfriend”. The nice thing about it was, it really did take the pressure off… but the key for me, was whilst it was a confusing time… I never felt used, and I always felt safe. His companionship (with or without being my boyfriend) just made me happy (and also provided much bar room problem-solving for my girlfriends) =D ) So glad to hear you’re in such a content space! Props to you!

  22. Adults today need to learn how to be direct. This noncommittal bullshit the gay community is obsessed with is honestly the best way to waste moments of your life better spent going after the things you know you want.

    “I just wanted to see how things went..” Okay. Well, how’s about next time you want to jerk something around without the threat of any sort of commitment weighing on your underdeveloped emotional maturity, you just stay home and find a nice porn to watch. ??

  23. The photo is surreal, and you look deranged. I love it. I also want a lettuce so good it puts me in a trance.

  24. I think its nice when people are pro-active about hanging out and seeing where things go. Maybe there will be a connection between you two, maybe not. Definitely sounded like two casual dates on his end to see if you two would hit it off.

  25. I’m not a fan of dating either. I prefer a more natural approach, When you least expect it, you will meet someone worthwhile

  26. I’m a little baffled. How gorgeous was this guy? You’re pretty damn good looking yourself. Personally, I think if you bring someone to a dinner party, it’s a date. Hanging out is like grabbing a few drinks or getting coffee or going for a run.

  27. This post reminds me that, for the most part, we’re all just doing the best we can. I bet Brandon was wondering the same thing you were, and thought the whole thing was just as awkward. Life is just hella confusing sometimes. xoxo

  28. Maybe you should expand your type, or see what else is out there? I think we are all guilty of trying to find someone to fit into this idealized bubble of who we should date, but at some point we have to evolve. I’ve read your blog for a while and it doesn’t seem like you have, I’m not saying you have to date someone that doesn’t look like a model or isn’t white…but maybe you keep getting your heart broken because you are trying to find someone to fit into what you think your life should look like instead of what it is. If you shop for men in the hot isle of the grocery store, don’t be surprised when they continually return you for something fresher and cuter when they’ve used you up.

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