That’s what she says to me every few weeks we meet: “Dating is supposed to be fun.” To which my immediate reply is, “Is it?” That certainly hasn’t been my experience, at least not in totality. And as I write this, I’ve come into contact with a couple other stories that have made me think that we as humans don’t always have fun seeking romantic relationships with other humans.
My brother describes it as “work.” To be fair, I gave him that definition, because as he’s trying to enter the dating market a couple years after being in recovery, he’s struggling with the crazy shit you have to deal with when you’re seeking the emotional attention of someone else.
He met a girl through program. He liked her. He asked her on a date. She agreed. A few hours before the date, he made the fatal mistake of asking my mom for advice. She, being a divorced woman whose husband had extramarital affairs throughout their marriage before leaving her for another woman, naturally told him not to go. That’s unfair, my mom probably told him not to go because my brother can get obsessive over women. As though him opening his heart to them is such an act of complete and utter vulnerability that all he can think about is whether they like him, will wrong him, will love him in the end. He and I both share this trait, though I’ve just gotten better at managing it. Knowing this, my mom told him to not go because she didn’t want that to happen again. Still, bad advice to someone a few hours out from a date they’re really excited about.
My brother canceled. The girl was upset, called him a flake. A few days of agony ensued where my brother called me lamenting that he ever canceled and asking himself, “Why didn’t I just go on the date?” I told him he could’ve. That it could’ve just been a date, that he would use it as information and if they weren’t the right fit or he started feeling obsessive or consumed by the relationship, that he could leave later. But we all do a lot of “would’ve, could’ve, should’ve” when what we really need to deal with is the reality of our life.
A day or so passed, and my brother ended up hanging with mutual friends of theirs and ran into her. Awkwardness ensued. But then, a stalemate. Acceptance. Then they started to have fun. Connect. And a spark opened up again. She called him that night to apologize for being cold to him after he flaked on her. He told her he was just scared. That he had issues with intimacy and was just getting back into the dating scene, that he didn’t know how to date, not really. She seemed receptive. They met for coffee to talk about what they wanted. He was vague. She was vague. They were both vague. Then, when the time came for them to go on a date, she resisted. Not in a reasoned, communicative way. In a way that was pithy, defensive, protective. She, like him, was probably hurt one too many times, and so didn’t quite know how to proceed with someone she was wary of. He, on the other hand, was desperate to start something with her because he had already gone through the back/forth in his head about what not to do and had decided to move forward anyway. She wasn’t ready.
This morning he gave me a call to say that she had told him she didn’t want to keep trying, that they should just call it a day. He told me this with a somber tone, regret in his voice. When just the day before he had been raging, upset that she was being noncommittal and telling him he was just going to cancel again if she agreed to a date. But I could hear it in his voice: exhaustion. Sadness. Exhaustion from the sadness. He accepted defeat and said he’d take the next few months to work on himself.
And that’s his dating story, albeit only recently, and it used to be my dating story when I was much, much younger. But it’s also part of my story now. Because I’m just as scared as he is about starting something with a guy I really like. And I know other friends who are scared or unsure of themselves in other dating situations, whether it’s to ask someone out on a date, to ask whether someone wants to be their boyfriend, or simply to go on a date at all.
Which brings me back to the statement my therapist likes to make: “Dating is supposed to be fun.” I agree with her. I repeated this back to my brother on a voice message over the last week as I tried to talk him through the icky, sticky situation of dating where you have to consider other people’s feelings, muddle through your own feelings, and somehow try to have fun in the process.
But it’s hard. It’s difficult to date, especially now. I shouldn’t say “especially,” I’m sure dating was just as hard in the past as it is now. But past lovers didn’t have to deal with social media. Or dating apps. Grindr. The existence of Sex Addicts Anonymous. Self-help language and books that dictate how you should love someone, what to do when you’re in love, how to be. We’re inundated with advice, astrology, and all kinds of things around dating that feed into our own views, past experiences or traumas.
I would say, in my experience, I’ve heard people complain more about dating than rejoice in it. Why is that? Is it really so much work? And then you hear things like, “when you meet the right person, it won’t feel so much like work.” Only to be contradicted later when someone, probably the same someone, equally says, “Marriage is supposed to be work. Love is work.” What the fuck? How can both of those things be true at once?
For me, dating is work. My goal in dating for the past few years has been to try to make it more fun than work. The only way I’m able to do that is by doing work on myself. So, I suppose it’s still work, but at least the energy expenditure is going into me rather than dating itself. I can only speak from my experience, so I’ll tell you why it is work for me.
For one, I come from a dysfunctional family. I know lots of people say this, so it can sound exaggerated, but it’s core to my identity so I’ll say it with my chest. I come from a dysfunctional family. I didn’t grow up thinking that the world was safe and warm, but rather scary and cold, that what you enjoyed one day could be taken from you the next and things never seemed to stay the same. I witnessed arguments that turned into physical violence. I witnessed what happens when someone drinks too much and embarrasses their family sitting around them in a public restaurant. I witnessed the fear of not being able to speak about any of it with my friends at school because the situation could be much worse if someone took me away from my family just to “protect me.” Or so I was told.
But I also experienced love. I wrote an essay for my application to Yale in high school that was focused on my parent’s love (I guess I’ve always been writing about this stuff, huh?). At 17, I was convinced my parents loved each other, deep down. Past all the hate, adultery, verbal abuse and trauma. They were in love with each other, because I could see it. I could see the way they’d spend hours together just whiling away the time, playing dominos, watching true crime, sharing an artichoke with garlic dip. How my dad would wake up at the crack of dawn whilst we were sleeping in our beds in some Palm Springs hotel and set out a lounge chair for my mom, my brother, and me in the best spot by the pool, laying out 2 towels on each chair so the plastic rungs wouldn’t burn our skin, and setting up my mom’s People magazines. I could see the way they laughed together, joked together, understood each other.
And because they had passed that love on to me. My dad never shied away from hugging me or telling me he loved me. Kissing me on the forehead and scratching my back when I asked him. He was barely around when I was growing up, but I never questioned that he loved me, just that he didn’t pay enough attention to me. I was more concerned with making him notice me than I was about making him love me. My mom was a cornucopia of love. On her best days, she was my best friend. I never wanted for my needs to be taken care of, at least physically. I always had food in the refrigerator, new clothes for school, as many books as I could ask for. She loved me so much that by the time I got to high school, it was suffocating. It was just us two in the house — my brother had been forced to move in with my dad because he was causing problems at home — and we reverberated off each other as I started to become more independent and her drinking got worse. But I never doubted that she loved me, just that she was incapable of giving me the kind of love that I felt was least traumatizing.
I say dysfunctional for a reason, because we had both love and pain in our family. And my brother and I struggled with that. We also bonded over it. We were each other’s constants amid the family fights, long, drawn-out drunken dinners, and come-and-go absences of my dad. And yet, we were also so different. He was shy and quiet, rebellious at school. I was extroverted and loud, the perfect student. I was also gay whereas he was straight. We both dated girls in school. But my relationships were with friends, built on shared interests and affection. Whereas he dated girls who, from what I heard from him, didn’t take his feelings into account and often rebuffed him in ways that made him question his worth. But was that them, or how we were brought up?
Growing up closeted in a white, conservative town only increased my being secretive about anything having to do with my personal world. It wasn’t until my senior year of high school, when I started dating my best friend, that I finally opened up to someone about how my mother drank. I had never talked about it before. It would take me even longer to open up to anyone about my sexuality, including myself.
I say all this because I’m trying to build a history around why dating can be work for me and my brother. I think both of us struggle with a sense of self-worth. It’s hard for us to fathom that someone would truly take an interest in us, because we grew up trying to hide as much of ourselves as we could just to survive in a dynamic where the more attention you brought to yourself, the more likely you were to be scrutinized, critiqued, or simply targeted. For him, he’s been further challenged by being shy and reserved, not being as open to taking initiative as someone who feels a lot safer in receiving rejection. But I have that fear of rejection, too. We all have that fear. It’s scary!
I think the hardest part about dating in your 30s is that you start to become self-aware of all the ways in which you’ve made it harder for yourself to date. You’re also aware of the hurt that can await you at the end of a new relationship. You’re aware of your wants and desires, but also still unsure whether those wants and desires are concrete enough to help you weed out someone who’s “wrong” for you. You’re adult enough to know that there is no “right” or “wrong” for you, there’s just people who either fit with your life or don’t. And yet you still find yourself checking the compatibility of your two astrology signs because you want someone other than yourself to tell you whether you should keep pursuing it (hello, new Costar friend!).
For me, what I’ve recently realized is that I have all these rules surrounding dating that I never examined before. They’ve come up a couple times lately as I’ve been seeing someone more consistently, and when he asks me about them, I find myself stuttering and unable to defend exactly why I have that rule or where it comes from. Just that it is a rule I feel in my gut. For fun, let’s examine some of these rules:
Don’t see them more than once a week.
You can’t say “I love you” or call them “baby” until you’re boyfriends.
You can’t be boyfriends until you’ve known them at least 2-3 months.
Don’t introduce them to your family until you’re sure it’s something real. (This is a big one for me, I have to know you can put up with the crazy)
No more than one or two sleepovers a week.
Don’t let them leave a toothbrush by your sink unless you’re okay with them being there consistently.
Don’t introduce them to your friends too soon. (I break this one often)
Don’t lean on them for emotional support until you’ve been dating for a long while. (I think this comes from not being codependent on a man, the way my mother was)
Don’t date where you eat. (Or rather, don’t date someone who’s going to make it difficult for you to maintain your normal day-to-day life like your job, your friend group, etc.)
Don’t make promises you can’t keep. (This includes making plans too far in the future, telling them you’ll be theirs forever, etc)
No marathon first dates. (Too many first dates that turned into weekends together that turned into me hating them by the end of that same week)
Make sure you see them angry, sad, and frustrated before committing them to something long-term.
I used to think these rules were to protect them. I went through many years of breaking hearts of boys I wasn’t quite sure of. So, I developed some rules to make sure I was tempering any proclivities of mine to love-bomb someone then ditch them. But as I started thinking about these more recently, I’ve realized they’re more to protect me. I’m pretty closed off. I don’t let anyone in. I didn’t even tell my best friend about my mom’s alcoholism until we’d known each other for over a year.
It’s the same with dating. I’m scared of being hurt, deep down. I’ve had experiences in the past where I’ve given myself wholeheartedly to someone, only to be shattered by them later. True, it’s only happened once or twice, but that’s because I got really good at protecting myself from that possibility. So good, in fact, that I started to lose sight of what it was I wanted in a man at all. It became harder and harder to differentiate between someone who made me forget about loneliness for a while vs someone I was actually, deeply interested in. At 33, I’ve gotten much better at dating men who make sense which is probably why my relationships have lasted longer than in my twenties.
But there’s still that guard up. And if you know me, you know that I think of myself as an open, loving person. So it’s a bit of a shock to realize that actually, I enter into most dating situations with the idea that they have to prove themselves to me. Which, if you’re expecting someone to prove themselves to you, you’re already starting on an odd foot in the relationship because there’s a subtle power dynamic. How can you be truly open to someone if you’re already expecting them to cause you doubt and pain later? Until they prove you wrong? It just doesn’t work that way.
Another thing my therapist recommends, when I’m starting to think all these things I’ve been thinking and writing about, especially whilst on a date with someone, is that I ask myself, “What can I do in this moment to be present?” I told my brother this recently and advised the reason behind this question is to make sure you don’t miss what’s happening in the present. Because all of the above is comprised of fear, doubt, ambiguity, etc about your own past or about your unclear future. None of it has to do with the present. Because in the present, you can probably tell when someone is being hurtful to you. You can experience it first-hand. And you can also experience when someone is being kind and loving. And it’s these experiences that add up to knowing whether someone is worth pursuing. You can’t experience those things that give you clarity if you’re so busy thinking about what’s happened to you in the past or what could happen between the two of you in the future. This has helped me immensely as I start to spiral whilst in the midst of a date that’s either going really well or really poorly. By being present, I’m also able to have a little more fun. After all, we’re just together for the night. Or for another week or two. Or for the next ten years of our lives. Who knows? And if it’s taken down a notch in terms of the stakes, then I’m able to let loose a little more and forget some of the rules above. I’m actually able to experience the time I’m spending with this person who interests and attracts me. And I can make better decisions about whether I want to see them again.
Anyway, I hope this essay hasn’t been too ramble-y. I encourage you to think about the last time you heard someone call dating “fun.” And whether you think it’s fun yourself. Then ask yourself why.
Your first rule got me really curious. Is it to reduce the rollercoaster-like jump into a new, amazing/thrilling, desperately intense relationship after only a couple of dates?