I Went on Over 100 Online Dates in 5 Years—Here’s What I Learned

It was the fall of 2013, and I had just moved to San Francisco. The tech industry was booming, and everything felt exciting and fresh. Tinder had just been released the year prior and my friends were ready to share their online dating advice and experiences. They had dove head-first into this new-to-me-world and reflected openly on the trials and errors of app-based dating. Hesitant as I was, I also wanted in. Possibility loomed around every corner of the city and within the device I could access at any moment. I remember my initial thoughts: You could scroll through (and perhaps even match with) a million hot guys, and maybe, just maybe, your true love was right there, waiting at your fingertips.

It quickly became evident that gone were the days of trying to catch someone’s eye at a bar. “Meet-cutes” felt like something only meant for fairytales directed by Nora Ephron, and checking Craiglist’s Missed Connections? An antiquated approach.

Well, fast forward five years and three months. Unbeknownst to me, I was headed out on a first date with my future husband. (Spoiler: We met on an app—Bumble if you were curious.) Not only have I found romantic love on these digital platforms, but I’ve had the joy of making lifelong friends “on the apps,” (Brian, I’m looking at you). Talking to and meeting people in this way, I’ve learned a ton about myself. I’ve also been introduced to new ideas, cool places, and different theories on life, love, religion—and so much more.

Honestly, while some dates were total duds, I also had some majorly inspiring conversations, learned some big (and much-needed) lessons, and honed in some killer text banter skills.

Feature image by Kristen Kilpatrick.

The Ups and the Downs of Online Dating

But for some reason, I’m still now always “proud” of the amount of online dating I’ve conquered. I say conquered emphatically, because if you’ve ever online dated, babe you know—you’re a trooper. I struggle with the reality that finding love has been reduced to a reward-based and dopamine-inducing yearning to be noticed, matched, liked, and desired. The quick flick of a finger left, right, up, or down through profiles of people who, just like you, are beautiful and imperfect humans searching for love and connection troubles me at times.

The whole notion is frankly wild. And while I see the good and the bad of online dating, I’m learning to drop the stigma. I’m honestly a firm believer that online dating is such a great tool for finding love… or at least having fun! (Hot take: If you want, try using the apps for both.) After all, I never would have met my husband if it wasn’t for Bumble, and the truth is that the stars really do have to align for things to work out.

Perhaps online dating isn’t the old school love we all grew up yearning for. You know the one: Where we bump into prince(ess) charming walking our dog or whatever. However, online dating is so good for so many reasons. Learning how to navigate it without flailing (too much), letting the apps do the work for you, and going in with confidence to what could be your first date with Mr. or Mrs. Forever is an art.

I learned *a lot* in my five years of online dating and I’ve polled my girlfriends who are still in the game for their online dating advice. Keep reading for our favorite tips on how to slay the apps, not lose yourself in the game—and perhaps most important, stay sane.

If You’re Into It, Prioritize Meeting In Person

I’m kicking things off with my biggest tip. My first online dating experience is burned into my mind. Looking back on it, I did everything wrong. I matched with a guy who seemed cute and cool. We had the best text banter, and we talked A LOT. I’m talking 2-3 weeks of back-and-forth texting all day long. There were a few hours-long phone calls thrown into the mix, and if memory serves me right, I think we even emailed each other. Oh, and did I mention we followed each other on Instagram prior to meeting up?

Essentially, I fell head over heels for the dude without ever having seen him in person. Catfish me now, am I right? When the big date finally came, there was some major pressure on the situation. Suffice it to say, the date was a total flop. I wasn’t attracted to him nearly as much as I thought I’d be and the connect just wasn’t there. I hate to say it, but he totally didn’t look like his photos. Upon further reflection, I feel like the universe was sending me a wake-up call to quit acting like a fool. I had built it up so much in my head that I was a little heartbroken that it didn’t work out. After that, I decided I was done wasting my precious time and energy getting to know men too well before we met up. Had we done so earlier, we at least would’ve had the opportunity to determine if there was a spark.

Personally, I think it feels safer and more protective of your time and energy not to dig in too deep until you know it’s worth it. There are a lot of fish in the online dating sea, and you can easily get sucked into wasting some major time. Don’t forget: You and every minute of your time is valuable! The time you pour into online dating is also time you could be pouring into you. You are way more than worth it.

If you have the bandwidth, give shorter, more casual dates a try. Chatting just enough to be sure the person doesn’t creep you out and ensuring you have a few things in common then scheduling a meet-up is the way to go. It can be a morning coffee, heading to a yoga class together, or a short post-work happy-hour. Be sure too, to clarify the start and end time. Try something like this: “I’m pretty busy these days, but I’d love to squeeze in a quick coffee. I’ll have to get to work by 9 a.m., but could we meet from 8 to 9?” It’s honestly more fun if you meet quickly (while sober) and notice a connection. Have to wait a little bit for more can be totally exciting.

What You See Is What You Get (Kind Of)

Oftentimes, we project onto photos, profiles, and texts who we want the other person to be. It’s easy to ignore some red flags in photos if you see a few things that pique your interest and create an idea of who the person is. I’d often get back from a bummer date only to re-analyze someone’s photos or profile and notice the thing I wasn’t into on the date.

An example: It may sound vain, but we all have different physical attributes that are important to us. If you’re a teeth person, make sure you see those bright whites in photos. If it’s style you’re attracted to, look closely at their full-body shots. If those things are important to you, you’ll save time and energy by being a little detail-oriented while looking through their pics. Also, don’t lie to yourself. If there’s something on their profile that you think would be hard-pass, trust it or ask about it in advance. People don’t casually throw details on their profiles if they aren’t important to them. Don’t waste time on a date if you don’t like what you see. Your eyes don’t lie.

Let Filters Do the Work for You 

Instead of swiping through the profile of every single eligible person in New York, use apps that’ll help you save precious time. Algorithms are soooo much smarter than they used to be. Apps like Hinge feed you matches they think would be great for you. They use data from previous dates you’ve been on and data from who you engage with the most to match you moving forward. The more you use the app and give feedback, the better it works for you. Spend some time setting your filters carefully and adding important details that matter to you. From there, sit back and watch what happens. You might be surprised.

Use Online Dating as a Tool

Again, don’t waste your precious time sitting in bar after bar with person after person if it’s not fulfilling you. When I lived in LA, I was brand-new to the area with hardly any friends. I used online dating as a way to do all of the fun things in LA I wanted to do anyway. Let these men and women accompany you on your journey through the world.

Excited about a new exhibit at a museum? Want to try a new restaurant? Need to walk your dog every day after work? Always prioritize safety and have someone meet you in public, not at home, but bring the people to you! I also like keeping alcohol out of the mix for a few dates if possible. It helps you see the other person with clarity—no booze blinders or lowered inhibition included.

Never Hide the Real You

It’s really easy to get suuuuper pumped about someone and then act like a total weirdo because you’re nervous. I realized a few years into the game that the guys who liked me the most were the ones I was less intimidated by. When I was with someone I had built up in my head, I got nervous and wouldn’t let my best side show, or I’d act how I thought they wanted me to. It sounds weird but it’s very common. It’s human to put on a front or try hard to be cool when you overthink things.

Try your hardest to talk yourself up, remind yourself you’re valuable, worthy, and awesome, and let your fun, relaxed, and most true self shine through. Don’t overthink it. Don’t try to be anyone you’re not. People can 100% feel authenticity and confidence. You got this babe!

Start Off With Low Expectations

The annoying truth about online dating is that we’re all dating multiple people at once until we’re not. It doesn’t feel good when you meet someone you’re pumped about only to come to the realization that they may still be dating a few other people. The apps make it easy to connect a lot, quickly, and with tons of people. Realistically, and without any bad intentions, you and the total cutie you told all your friends about may have an amazing time together. But the truth is, you may also each have a few more dates scheduled next week. That’s okay! Remember: If the connection is there, other people will slowly fade away, and you both won’t want to see anyone else when the time feels right. But know that there’s no way to guarantee that the other person isn’t falling in love with someone else.

Protect your heart and keep expectations low at the beginning. Keep your brain from getting too excited and take things for what they are as they come. It’s hard, but it’s crucial. It’s super easy to get overly excited, and when it happens over and over (and over) again, it can be soul-crushing. Tread lightly, take it easy and breezy, and never forget you’re a catch. Be realistic though, and remind yourself that sometimes, it just doesn’t work out—even when you expect it to. But when it really clicks, you’ll know.When it really clicks though, you will know and it’s so so sweet!

Trust Your Gut 

If I had a dollar for every time my gut told me something I wish I listened to in the dating game, I’d be a rich woman. Well, at least 100 bucks richer. Start listening to that little voice that’s telling you she might not be a good fit, or that this issue with his ex-girlfriend is definitely not going away despite what he says. Trust me, it’ll change the way you navigate dating. If alarms are sounding deep inside, do yourself a favor and tune in. It can feel scary to listen at first, but I can’t stress how much you won’t regret it.

Be a Good Human—Don’t Ghost People

There’s nothing worse than going on a date, having an amazing time, and then never hearing from the person again. I had a pre-written text saved in the notes of my phone that I’d systematically send to every date that didn’t work out. This way, I wouldn’t put it off or forget and feel bad about it later. Try the following for inspiration.

“Hi! Thanks for the date, it was great to meet you! I honestly wasn’t feeling anything romantic, but I wish you the best of luck finding someone awesome <3” 

Boom—done! You’re kind, you’re honest, and you’re respectful. It’ll definitely pay off one day either karmically or coincidentally. The Golden Rule totally applies here: If you’re 100% not wanting to see them again, no matter the reason, it pays to be kind. Note: Unless they were creepy or harassed you, then you owe them absolutely nothing. Here are a few things to think about if you’re tempted to ghost someone.

Stop Swiping Like Crazy

This is another big one. The world is FULL of distractions. We’re constantly bombarded with emails, texts, Slack messages, social life, familial obligations, and so on. It feels really good to be intentional about the way we move through the world and not just totally obliterated by an insane amount of potential. I often wonder how anyone online dating could ever meet the right person if they’re constantly focusing on the next date.

No joke, I would sometimes arrange 3-4 dates a week just because I could and I was being asked out. This turned into me going on a lot of dates I wasn’t into. If I could take those days back and study a foreign language, get a little more sleep and a little less booze, or even just have taken a bubble bath instead, I would three times over. When I finally slowed down and stopped the frantic dating, I met someone who mattered. Call it timing or luck, but I think sometimes we need to focus on what’s right in front of us in this hyper-distractible world. Don’t date just to date. Be intentional, be humble, be kind, and don’t be afraid to slow down.

Talk About Deleting the Apps When It’s Time

Lastly, don’t be afraid to have a conversation about deleting the apps when things are going well. This is a normal thing that a lot of people do and it feels great. It can be really hard and scary for some people to have conversations like this. But the truth is that you really want (and deserve) to know.

My husband and I actually deleted Bumble at the same time. Kinda cute? My only other advice is that if you end up meeting someone you fall head over heels for, screenshot the first few messages you exchanged to keep for later. I really wish I could read the cheesy things we said to each other or show our future kids the weird technology we used to meet. That’s right, in the world of dating apps, you can still be sentimental.

If you taking anything from my online dating advice, I hope it’s this: Navigate the waters thoughtfully, always put yourself first, tread lightly with your heart and expectations, and always be yourself.