30 First Dates
Dating in 2018 is fascinating. Not so fascinating that if you aren’t doing it you need to stop everything and make it happen. No, don’t do that, lol. More in the way that if you are currently dating, put your goggles on and embrace the opportunity for your life to be one very active laboratory.
I’ve been on this grind the past few years. For those in the not-currently-dating community I’m here as your eyes into what is not HBO Sex and the City, but also not not that.
I do this at the risk of a couple things. First, I will inevitably bore my dad to tears (and complaints) with yet more stories of my boyfriends or lacks thereof.
Second, a few times now I’ve been faced with the reality that someone I date might actually read something I’ve written. About a month into seeing a guy recently he sent me an email with the title of my own blog post and a question mark. Things will continue to get weirder if more of what I write is about dating. Having weighed this risk, I’ve decided to treat it as an unexpected but welcome filter. Would I want to be with someone who isn’t into my sharing of experience, and potentially up for being subject of that experience? Probably not. Take me or leave me, as they say. My dad has to. ;)
For the majority of my teenage - midtwenties years I held the strong conviction that there was an ocean out there and the biggest danger at sea was settling on my fish too soon. That would be the failure of my lifetime. I remember when the article To Fall In Love With Anyone, Do This came out in 2015 my first thought wasn’t “Oh cool now I have the key to falling in love”, it was “Oh fuck I will NEVER do this because what if I do it with the wrong person.”
So it seems only appropriate that life now has me scouring the best city in the world for the best of its men. And while my experience of fishing hasn’t been perfect, and many times over I’ve wanted to just lie on the dock and wait, it’s definitely one of the most epic learning opportunities I’ve ever had. It can be incredibly fun and it can be incredibly hard work — but foremost I’m incredibly grateful for it.
By now I’d say I’ve probably been on at least 30 first dates — perhaps many more, I’m not even sure how to go back and count. (In the beginning I didn’t think to put them on my calendar. Times have changed.) When I started I’d go in with no expectations and a pretty open mind. Like, not even a firm expectation that he’d show up. I just didn’t know. The process then was so foreign to me I couldn’t stretch my imagination enough to form a hope either good or bad for how the thing could go.
Now that I’ve had both very good and pretty bad my tune has changed a bit.
For starters I only go if I am certain he is coming too.
From there, I think less these days about the specifics of the attraction, considerations like do we have similar interests? does he have a good job? do our schedules align? I try to think more simply are we enjoying ourselves? how do I feel around him? I can tell immediately if I feel drawn to someone, if I want to spend more time around them.
Meanwhile, a strange thing seemed to happen around the time I turned thirty. I started sensing guys sizing me up for wife potential, literally on date #1. We’d be sitting face to face and I’d witness wheels start to turn when the conversation came to exercise routines, how we like to eat, entrepreneurial aspirations, places we like to vacation — immediately I’d see the mental box-checking begin. One time, on a really good first date a few hours and beers in, this dude said out loud (holding up a finger at a time), “I’m pleasantly surprised by you! You’re smart. ✔️ You’re beautiful. ✔️ You’re moderately funny.” 🙄
Either I wasn’t noticing this before or it’s happening more now, idk. Regardless, in the bizarre 2018 dating model, there’s a ton of pressure to hit it off the very first time you meet. If the connection isn’t right or enough boxes aren’t checked there will be no moving forward.
After 30+ first dates that have taken varied routes to nowhere, I have asked myself A LOT of questions. Allow me to let you behind the window of the interrogation room.
What’s the best way to get a date?
I might in the past have said (actually I did say) that organically meeting a stranger, in person, somewhere you really like — a coffee shop or yoga class or bar — and hitting it off is the ideal scenario. But the new normalness and ease of meeting someone on an app has made this formerly desirable situation seem unnecessarily difficult and even, almost, creepy at times.
(I won’t commit fully to the idea that it is creepy and I do hold out hope for this scenario. Nonetheless I can’t help but acknowledge the increase in dates I hear about that go sour starting this way, alongside the increase in tales of dating success birthed from the initial safety of an app.)
All things considered, I now think the best way to strike up a fling is by connecting on social media (likely Instagram) or via email, with a removed (could be someone you know loosely or knew a long time ago, a friend of a friend, etc.) but not complete stranger, and taking it to the streets.
Somebody slap me. Can’t even believe this is my analysis.
This, however, is not the easiest way. The fastest and easiest way to a date is via an app.
I will add here for those who aren’t finding it easy to get to the first date stage, I hear you. I had this challenge for a while. I didn’t understand when I’d learn about friends who were on like a Monday, Wednesday, Thursday, Sunday dating schedule. How were they getting all these dates?!
Having transitioned to the 30+ (age and dates) club, I now believe it’s all about commitment to the cause and intention. When your head’s really in the game it’s not so difficult to make happen. Essentially you expand your acceptable criteria, up your involvement and agree to increase the number of nights you sacrifice your lovely workout, healthy dinner and enjoyable glass of wine on the couch.
Would my exes pass the first date test?
Recently I started to wonder how any of my past partners and I would fare in the 2018 dating gauntlet. All the relationships I’ve been in for more than a couple of months grew out of non-dating-time spent together before we began to date. I asked myself if we’d have gotten where we did, subjected to the dating process du jour. And more deeply, given that it really hasn’t yet, will this stranger-forward model ever work for me?
To the question of how my former bfs would fare, I actually do think we may have made it out alive. If you account for the time in my life that we met and you put us on a random first date I’d be drawn to and interested by any of them still.
In what way can I use this in my current experience? I don’t really know — I try to let each thing be its own. But I guess the takeaway is that even though today’s method for forming relationships sometimes seems insane, I think it can ultimately lead us to spend time with the people we’re supposed to.
Am I meant to date girls?
This one really threw me for a loop. When you’ve been striking out in one game for long enough, a funny question starts to emerge — am I playing the wrong gd game?!
I never questioned my sexuality growing up. From the time I was 13 I found myself attracted to and in relationships with guys, no questions really to be asked.
But once I hit a long enough stretch without a permanent male partner I started to wonder, am I not meeting a man because I’m not supposed to meet a man? Am I looking in the wrong place? Was all the time I spent interested in guys a distraction from something else? A conditioning of society? Does the simple fact that I’m questioning this mean something?
Let me tell you, this is one v disorienting rabbit hole.
I think I’ve gone down it for several reasons. First, maybe it’s a question some of us are fated to address in order to better know who we are. I am way more afraid of getting stuck in the wrong relationship than of being alone. It’s a matter of truth — I’d rather face a challenging truth than allow myself to live a lie. So I think at a certain point I became willing to question what was a scary departure from the known, to avoid the more frightening possibility of ending up in the wrong reality.
I also think that personally — and things have moved this way societally too — I began opening up more to the human in everyone; man, woman or other. Soul connection has become most important to me, in all relationships. The differences we’ve maintained between genders for generations have started to soften. And so naturally I called to question the strict boundary in romantic relationships that’s always been present.
Where I’ve landed, for better or for worse, is rooted in my attraction to men. But the process of questioning it has been a meaningful one. It’s made me more tolerant and understanding, I hope. It’s made me more self-aware and discerning. It’s made me look at my preferences for what they are when they aren’t influenced by circumstance, like already being in a relationship or directed (without question) by norms.
As I write this I know I benefit from being able to share it. It’s a privilege I can do so without much consequence — a privilege not everyone has. I don’t think there are too many men who’d refuse to date me as a result of knowing that I’ve wondered these things. Unfortunately it’s not a two way street. I’m ashamed to say I would probably feel differently about a guy if I were reading him write this. Another thing dating unquestionably reveals is our areas to grow in love.
What’s the best way to communicate “goodbye” in this dating context? At this rate, will I have to run around the city ducking men?
I don’t know what other craziness is going on out there, but I’ve gotten so many appreciative and kind texts in response to declining date #2 (or 3 or 4) that it really makes me wonder: are people just straight up in the habit of pretending things will move forward and disappearing? Is ghosting as widespread as some make it out to be?
I treat dating as an opportunity to sharpen my life skills. I’ve tried to use it as an avenue for practicing following my gut and being 100% true to what I want, how I feel and who I want to be. Therefore it demands of me my most respectful and clear communication.
A student of mine came to class fresh off a first date recently. She said she had a nice time but knew she didn’t want to see him again. I created a note in her phone with the below. Feel free to employ.
Thank you again for today! To be honest I’m not feeling a super strong connection and I wouldn’t want to waste your time, but thank you so much again it was really great meeting you and chatting. :)
True. Kind. Necessary.
What is first date touch/kiss etiquette?
Idk, everyone and every situation is different, obviously. But one thing I’ve observed is this awkward energy when guys maybe feel like they’re supposed to go in for it on the first date to let you know they like you? If both people are looking for a longterm thing, I think it’s safe to assume that you can convey your likeness in words and wait a sec.
(Third risk I run in writing this, every guy will be afraid to kiss me forever.)
Why are my patterned fears coming up so damned fast?
In my first two relationships I’d get these bouts of anxiety as things were progressing. I’d jump way ahead in my mind and get scared by the permanence of attaching myself to someone for fear of all the other people I’d then potentially miss out on. Of course not the healthiest reaction, and definitely an indication of a particular attachment style, but not unimaginable based on the real scenario of my real budding relationships.
HOWEVER, I now find this happening at a much more questionably (un)healthy moment. I can be about to go on a first date with someone, liking what I know about them (which is usually limited to how they look in a few pictures and perhaps how they spend their 9-5 time and weekends) and have moments of gripping dread that I’ve removed myself from the ocean of other possibilities.
The realization for me has been that it all happens so much faster these days and these ways, anxieties included. I try to be on alert for when I need to separate myself from my baseless thoughts and fears.
To work out (/do some other thing that’s good for me) or to go on date?
The weeknight dilemma. It simply is just really hard to get a workout in, get date-ready and get to bed by 10pm. I try not to compromise other activities for a date more than once in a week, but I guess I often fail at this too.
Are there absolute recipes for failure?
I’ve been on allll sorts of first dates — from quick coffees between meetings to baseball games that reach extra innings.
The consistent recipe for disaster in my experience is walk dates. They never work. I really don’t know why, as they seem like such a good idea. You can go on a walk date any time of day for any amount of time — you’re not reliant on any business’s hours. It’s always nice to get outside. You aren’t required to consume another cocktail or cup of coffee. There are few distractions. Golden ticket, no?
But honestly, for me at least, they just never seem to work out. One time I was on a pleasant first date walk in Prospect Park and out of the blue the guy asked me to stop for a second. He walked 10 feet away, turned around and peed off the side of the trail.
I don’t really go on walk dates anymore.
Do I have a type? Has it changed over time?
One thing I noticed myself doing when I reached a certain number of overall dates was that I’d start to seesaw with my preferences. I’d go on a date with a lawyer and then, out of the non-success of that, decide to look for guys who work in the fitness industry. I’d go out with someone who lived all the way uptown and after the hassle of that, limit my search to guys in Williamsburg. I’d get really curious about guys from other backgrounds and next decide I need a nice Jewish boy.
Some call it learning and honing a type, I call it quite exhausting actually. And ultimately a bit too focused on specific superficial criteria. Realizing this was happening caused me to adopt the approach of questioning only energetic connection during pre-meeting convos and first few dates.
I do have an energetic type though, for sure. And it hasn’t really changed all that much in the past decade and a half of my life, but it did get a new name this year. What my friend Jenny and I used to define as “Leaders of the Pack”, the zeitgeist has rebranded BDE. I am absolutely a sucker for BDE. When I type BDE in my iPhone, it comes up as a word. That’s how real it is in my life.
I’ve made some pretty big changes over the past few years and I’ve been curious how this might impact or change the sort of man I’m interested in dating. I was worried about how my new routines — meditating early in the morning, limiting (for a long time eliminating) drinking, trading fantasy sports for women’s circles — would be compatible with someone else’s. I’d never dated anyone who lived this way. I’d never lived this way.
After experimentation and reflection I think I over-anticipated the change this would bring to my dating criteria. For some time I let the shift in my own interests lead me to guys who have different energetic makeups than I’d been attracted to for most of my life.
What I’ve learned is that a) the thread that connects all of my former flames is BDE which b) exists in men of every different walk of life, industry, area of interest. Lucky for me this means that no matter where my routines and interests lead me there is bound to be an energetic companion for me. Fingers crossed, anyway.
When do I say enough is enough?
Broadly, I don’t have the answer. I’ve been engaged in active dating for let’s say two years. When do I throw in the towel and seek a new hobby? We will see. But my enjoyment of it does ebb and flow, and generally I’ve tried to remind myself to take a step back when I’m not having fun. If I catch myself not looking forward to a date or feeling like it’s a hassle, that’s my indication it’s time to take a break.
So where do several dozen categorically unsuccessful first dates leave a romantic?
I used to be really stressed about when I’d meet the person I am to spend at least a lot of my future with. Every party, or night out or new job had the potential to be, had the pressure of being, the place I’d meet my man. I looked at the months, then the years, that passed without him as wasted time. I was disappointed, for example, that I lived many of my twenties without a partner.
But as time’s gone on I realize this fear has started to fade. Call it coming to terms with what is, call it finding a new perspective, call it growing up. What it actually is though, I think, is that oft-mentioned sense of wholeness we’re meant to find in ourselves. That which does not come from spending our time in the state of partnership, as badly as we may want that.
Having spent most of my formative years partnered up I didn’t learn this in the order many people do. I learned togetherness first and only now, post-adolescence, am I figuring out how to be content and complete on my own. Jerry Maguire and “you complete me” didn’t help either — still climbing uphill to shake that.
As I become more profoundly comfortable on my own, I increasingly realize that nothing is missing so long as I’m applying my gratitude and presence and desire for growth to each and every day. Thirty first dates have reminded me that it’s in the questions I ask myself along the way, and not the answers I seek, where life is lived.