My Own Dating Journey: 13 Lessons Learned

Written by our founder, Sarah.

Hi, I’m Sarah — founder of Strategy Journaling Co and the person who made The Date Book. I want to share some of what I learned from my own years of dating, mostly online. Those years were strange, sometimes bewildering, occasionally mortifying, and — eventually — how I met my fiancé, on Hinge. Along the way there were awkward first dates, a couple of real heartbreaks, a few people who became close friends, and a lot of figuring things out the slow way. Learning to actually enjoy online dating is what led me to build The Date Book.

Maybe you’re just starting out, or maybe you’ve been at this a while and want a fresh take. Either way, here’s the honest version. I went from someone terrified of online dating to someone who looks back on it with real fondness, and getting there taught me a lot — about dating, and about myself. What follows is thirteen of those lessons. It isn’t a how-to, and it isn’t a set of rules for you to follow. It’s just what I learned, mostly the slow way.

Lesson One: Dating is a skill, and I started out terrible at it

Is dating a skill? It certainly felt that way to me. I remember my first online date vividly – it was awkward. I had no idea what to talk about and we got stuck in small talk for most of the evening. I didn’t open up at all or ask any deeper questions. The location I suggested sucked — yes, it was my favorite burrito place, but it was noisy, crowded, and definitely not a place for romance. I even admitted to my date that it was my first time on an online date, and that I was nervous! He was sweet about it, but I think after that he realized this wasn’t going anywhere. I remember going home and thinking, “Well, that went well!” despite the total lack of a connection. My bar was not-getting-murdered-in-a-dark-alley, and anything above that was a win.

It took time for online dating to feel more natural. The more dates I went on, the more comfortable I got. I mean, how many situations are there where you meet a total stranger one-on-one and are stuck with them for an hour? It’s a social situation I had no practice with.

And first dates weren’t the only thing I had to get used to. Over time I got better at the whole thing. I learned to express my boundaries, to say “no” with kindness, and to tell sooner when a connection wasn’t the right fit. Things I’d have talked myself past on my first dates became instant dealbreakers by date fifteen. Like any skill, dating takes practice, and a fair amount of reflection. So if your first few (or many) dates don’t go as planned, or you feel awkward and uncomfortable — that was me too. It’s part of getting the hang of it.

Yes, I have a friend who married the first person she met online. It’s possible. But I wouldn’t expect it.

What helped me more was expecting the ups and downs, and being kind to myself while I found my feet.

Lesson Two: Even the bad dates were teaching me something

For a long time I was so fixated on the outcome — finding “the one,” settling down, the whole thing — that every date turned into a high-stakes interview. “Is this the person I’m going to spend my life with?” Talk about stressful. That pressure turned what should have been fun, low-key evenings into audition rounds, and that vibe is not exactly conducive to a relaxed, genuine connection.

It took me a while to notice that each date, even the less-than-stellar ones, was teaching me something. I was learning what I wanted (and what I didn’t), how I came across, how to carry a conversation with a stranger, a new corner of my own city. The dates weren’t just filler on the way to some endpoint. They were where the actual learning happened.

Once I stopped grading every date pass/fail, I had a much better time — and, funnily enough, I dated better too.

Lesson Three: It’s slower than it looks — a match isn’t a date

Just because there are a million people to swipe through doesn’t make getting an actual date instantaneous. I wish I’d understood that sooner. I assumed a match or a message meant a date was on the way. Nope — I had to wade through mountains of messageless matches (that one was partly my fault; I eventually learned to message first) and small talk that went nowhere before I even got to a first date. And then repeat, and repeat, and repeat.

A match is just step one; a message is step 1.1. People are busy and don’t always reply right away, and things pick up speed only with time. When someone dropped off for no clear reason, I tried not to take it personally — better to assume they got hit by a car than that they secretly hated me after I’d asked about their love of travel.

Lesson Four: Messaging first got me more dates (and a best friend)

There was once a guy I started chatting with on one app, and it fizzled. We rematched on another app a few weeks later and… crickets. What was even the point of rematching?

So I messaged him. This was early on, when I’d been marinating in the advice that women should never message first, and that if you have to put in any effort at all, he’s just not into you.

And it’s true — he wasn’t into me. It was obvious by the first date that we weren’t a romantic match. But what we were was a great platonic match. Long story short, eight years later, he’s still one of my best friends.

Had I not said “Hey! You! Let’s go out!” I never would have met one of my best friends. After that I messaged first a lot more. If you’re a woman dating men, it might feel strange at first — but it meant less time swiping and more time on actual dates. I’m not talking about chasing people who aren’t responding or aren’t carrying their half of the conversation. Just starting it, and seeing where it goes.

Lesson Five: Chemistry fooled me more than once

“I have chemistry with everyone,” my friend Paul told me.

Um, excuse me?

It’s true that Paul is one of the most charismatic people I know. People tell him their life story a couple of hours after meeting him.

But if Paul had chemistry with everyone, what did that mean for all the people he dated who thought they had something special with him?

It really got me thinking about chemistry. We hear a lot about that “spark” — the instant connection, the feeling you’ve known someone forever. It’s a real and exciting part of dating, and I’ve had those dates: conversation flowing, laughing until it hurt, that undeniable pull.

But what I learned is that chemistry can be misleading. It’s intoxicating, and it can make you feel like you’ve hit the jackpot. It just doesn’t always equal compatibility.

I remember one relationship where the chemistry was off the charts from the very first date — intense, all-consuming, like something out of a movie. But underneath it were real incompatibilities I was ignoring: our values didn’t line up, our communication styles clashed, we wanted different futures. The chemistry blinded me to all of it for a while. I was so caught up in the excitement that I explained away everything else — and that relationship crashed and burned, leaving me with a lot of heartache and one very clear lesson.

Chemistry is great; don’t get me wrong. It’s a wonderful ingredient. It’s just not the only one. Shared values, mutual respect, and similar goals matter at least as much for the long haul.

And my first date with my fiancé? Not obsessive chemistry at first sight. It grew over time. That might not sound romantic, but looking back it felt healthy, calm, and drama-free — all the things our relationship still is.

Lesson Six: I needed real breaks — apps-deleted breaks

One of the bigger things I had to learn was that it’s okay to step away. When I first started, I was so eager for a connection that I was constantly on the apps — swiping on my commute, on my lunch break, while watching TV. It became a constant hum in the background of my life.

And honestly? It drained me. I got irritable, took rejections too personally, and generally felt worse about the whole thing. It was like running a marathon at a sprint — eventually you hit a wall.

One time I’d had a particularly grim stretch — seven dates in two weeks, lots of “meh” conversations, someone who might have become a friend if I’d had any energy left, and one genuinely bizarre encounter I won’t get into. I was so disheartened I nearly deleted everything and quit.

Instead I took a real break. I deleted the apps off my phone (that part’s key, or the temptation wins), spent time with friends, threw myself into some hobbies, and gave myself permission to not think about dating for a while.

It worked wonders. When I came back, I was refreshed and much better able to handle the ups and downs. Dating shouldn’t feel like a chore that consumes your life. So if you’re burned out on swiping, taking a break is allowed.

Lesson Seven: I told my best friend I’d found love after date two (I had not)

After my second-ever online date, I texted my best friend to tell her I’d found love. I had not found love. It would be another eight years before I did.

When you’re excited about someone, it’s easy to run ahead and imagine the whole future before you’ve really met them. But actually getting to know a person takes time, and getting swept up after date two mostly sets you up for a harder landing if it doesn’t pan out. It also loads a lot of pressure onto both of you — like you’re trying to force a connection instead of letting it show up on its own.

So I learned to take it easier. To enjoy the early stretch of getting to know someone without leaping to the “forever” part. And if it didn’t work out? That was fine too. Not every date has to be a life-altering event. Sometimes it’s just a nice evening with someone new, and that counts for something on its own.

Lesson Eight: I started tracking my ratios (my slightly unhinged coping method)

Some of my friends look at me a little oddly when I bring this up. But here’s how I got through a string of bad dates:

I kept a record of every date I went on — a journal, naturally. I circled the ones that felt genuinely worth it, where even if it didn’t work out, I’d had a good time or learned something or made a friend. It turned out only about one in ten dates was really something. (No idea if that’s a good ratio or a bad one — yours might be better or worse.)

So every time I hit a long run of boring or bad dates, I’d tell myself:

“Number 10 is coming soon — my ratio’s gonna hold!”

Is that a complete misunderstanding of how probability works? Absolutely. Did it keep me from getting discouraged after a bunch of dates that went nowhere? Also yes.

Lesson Nine: A “hook” in my profile worked better than a joke

What on earth do you put in a dating profile? You get 300-ish characters to explain who you are. Roughly, you can:

• List qualities about yourself and what you’re looking for (unsexy but practical)
• Make a joke (better, but it doesn’t actually get a conversation going)
• Write what I call a “hook” that actually leads to dates

What’s a hook? I noticed I got way more messages and dates when I wrote something that made it easy to ask me out. “I’m trying to hit every coffee shop in Williamsburg” or “I’m really into rum cocktails lately — know any good tiki bars?” Those gave people an obvious opening instead of leaving us stuck in the messaging stage. Make it easy for your match, and you’ll end up on more dates.

And I didn’t keep the same profile the whole time — I had fun with it. It’s more of a creative exercise than a form to fill out.

Lesson Ten: I optimized the fun right out of it

For a while I lived in an apartment right above a bubble tea shop. “Perfect,” I thought. “I’ll have all my dates at Boba Guys, and if they suck I can just go back upstairs — barely any time wasted.”

(Can you tell I was feeling burnt out?)

Well. All my bubble tea dates absolutely sucked. I’d pop down when they arrived so I wouldn’t have to wait, get my regular order, sit at the same table, and have the same conversation, over and over and over.

I let it get rote, and eventually I couldn’t take it anymore. I stopped dating… and stopped drinking bubble tea. I managed to ruin two good things (a bubble tea spot downstairs, and dating) by over-optimizing until there was no life left in either.

Learn from my mistake.

Lesson Eleven: One person scrambled my judgment — and writing it down showed me why

I’m a pretty calm person. My life isn’t very dramatic, and my emotions rarely hit extremes.

So I was not prepared for what dating did to me.

There was this one person who could scramble my judgment completely. We’d have these intense, whirlwind dates that felt amazing in the moment — full of laughter and long conversations. Then, almost as fast, the doubts would creep in. I’d decide he wasn’t right for me, that we weren’t compatible, and that was that.

Except a week later, in a weak moment, I’d text him again. I’d get pulled back into that first rush, that feeling that maybe I’d been overthinking it. It was an endless loop of highs and lows, certainty and doubt, and my normally level-headed self was nowhere to be found. What was going on?

It was exhausting, and honestly a little embarrassing. That’s when I started writing about my dates more seriously.

At first it was just venting — getting the swirl out of my head and onto the page. But doing it after every date turned it into a record, and once it was a record I could see the thing I couldn’t feel my way to in the moment: the same loop, over and over, and my own habit of ignoring what I already knew. The volatility wasn’t really about him. It was about my own insecurities, and how easily I talked myself out of what my gut had already told me.

The more I wrote, the less I was at the mercy of whichever feeling was loudest that day. That clarity is, more or less, why you’re reading this on a journaling company’s blog — it’s the thing that eventually became The Date Book.

Lesson Twelve: I learned my own dating patterns

One of the most useful things I picked up was learning to spot my own dating patterns. It’s funny how blind we can be to our own habits, especially in relationships.

Early on, I had this tendency to give things a chance even when I knew in my heart it wasn’t going anywhere. I’d go on a second date, maybe a third, despite a nagging feeling we weren’t a fit. Part of me was afraid of hurting someone’s feelings; part of me was holding onto a faint hope things would magically improve.

But it wasn’t really fair — not to the other person, who might have been genuinely interested, and not to me, since it just dragged things out and kept me from meeting someone who might actually be a better match.

I remember one instance vividly. I was about to go on a third date with someone and feeling deeply lukewarm about it. I was trying to sound enthusiastic while we made plans, but my hesitation must have been obvious, because — bless them — they just noped out. “You know what? I can tell you’re not that into it. I don’t think this is going to work.” And they ended it.

It was a bit of a wake-up call. It made me realize I needed to be more honest — with myself and with other people — about how I actually felt. After that I got better at it: more decisive, quicker to stop dragging out things I already knew weren’t right, and more careful with other people’s time (and my own).

But everyone’s patterns are different. My best friend has the exact opposite tendency — she’s so selective she’ll write someone off after one date for the smallest reason. We tease each other about it constantly. The point is that you only learn your own patterns with time and attention: watching your behavior, your reactions, the choices you keep making. And once you can see them, you can start making more deliberate ones.

Lesson Thirteen: The one time I ignored my own safety rules

This one’s a bit dark (content warning for sexual assault, though not toward me).

I’d been having a great time dating, and nothing bad had happened, so when someone invited me to a breakfast first date at their apartment complex — they said they had no other time available — I ignored my own rule about not meeting in private places. We also had mutual friends, which lulled me into a false sense of security. How weird could this person be?

When I got there, they tried to get me up to their apartment instead of the public rooftop patio we’d agreed on. Their messages had been perfectly normal; in person they were nothing like them — genuinely bizarre. I was uncomfortable almost immediately. They offered to pay for a flight to India for the two of us, then tried to give me a copy of their book.

I said I wasn’t feeling comfortable, and I left before the DoorDashed breakfast even arrived. They messaged afterward to ask if I wanted to hang out again. Um, no?

Thank god I listened to myself and left, however awkward it felt in the moment. I found out later that this person had been accused of date rape — I don’t know whether it was before or after I met them. Having seen how they acted (and this short description really doesn’t do it justice), I have no trouble believing it.

It’s easy, after a run of good dates, to assume everyone you meet will be lovely. Please don’t let safety slide, especially on first dates. Meet somewhere public that you can both get to and leave from on your own. Stay sober enough to look after yourself. And if someone’s behavior makes you uncomfortable, don’t hesitate to block or report them, or to leave early. When it comes to your safety, drop the politeness instinct and just go.

In closing

If there’s one thing under all of these, it’s that there’s no single roadmap. Your version will look nothing like mine, and that’s fine — there’s no “right” timeline, and no one you’re secretly supposed to be keeping pace with. It’s easy to feel like you’re behind, or doing it wrong, when your experience doesn’t match your friends’ or what you see online. You’re not.

What actually helped me wasn’t a rule. It was paying attention — noticing what kept happening, being honest with myself about it, and writing enough of it down that I could finally see it clearly. That’s all the journaling really was: how I made sense of my own dating life, and, eventually, how I ended up with Ryan.

—Sarah