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Ask Kelly: Why Are All My Online Dates So Boring?

Also: Did 2020 kill dating? And, how to put yourself out there and make new friends.
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Love everything you write, Kelly! I'm in NYC and at 29, I'm totally burnt out on dating apps. So many of my friends have found their partners this way, but I'm wondering if you have any advice for navigating the overwhelming-ness of it all? I feel like I continually go on dates with guys I meet on apps that are fine, but I just never feel that excited about them or compelled to continue seeing them after a few dates. I try to keep an open mind and date people who don't immediately excite me on the app (since only so much of a person can be distilled into a short profile), but then I go on these lackluster/boring dates and I'm like "why aren't I pickier"? Any tips for what you found helpful to look for in a partner for yourself, and what could be useful in filtering through these boring men beforehand so I don't keep feeling so drained by dating? I want it to be fun again! – Caitlin

Dear Caitlin,

I hear you, and I’ve been there before. Dating apps can be unbelievably overwhelming and feel majorly frustrating if you let them. We all know they work (the amount of couples I know who met online is staggering), but the actual process of using them can make you want to throw your phone against the wall.

I’m going to challenge you a bit here….brace yourself. 😉 You used the word “boring” twice to describe both the typical dates that you go on, and the people you’ve gone on these dates with. What exactly do you mean by that? “Boring” is such an undescriptive word – do you mean that the dates themselves are uninteresting or repetitive (like strictly going for drinks or dinner and eating the same type of food over and over? That does sound boring), or maybe you don’t find the people you’re choosing to be intellectually stimulating or spontaneous? Maybe they’re a good listener, a little introverted, and not trying to dominate the conversation, and you find those traits “boring”? You tell me!

One thing to really dig deep about and consider: What do you want out of dating? You’re 29 and live in a big city, which means you could just as easily be looking for a thrilling weekend fling as a life partner–both of which are totally fine to want at this, or any point in your life–and that’s a question I can’t answer for you. If you’re secretly longing for a spicy month-long romance with a hot foreigner but you’ve convinced yourself you should be looking for someone stable with a 401(k) who will open doors for you, you’re setting yourself up for failure. Be honest: When you’re swiping right on dating apps, what are you looking for, really? Excitement or companionship?

I think it would be good to remember that when you meet someone for the first few times, you’re probably not going to let your freak flag fly. Right? Well, your dates aren’t doing that either. On a first date, most people are just trying to avoid disaster. So what you’re interpreting as a “boring” first date may actually just be your dinner partner trying not to make an ass out of themself. It might take a while for people to get comfortable enough with you to make weird noises, laugh really loudly, or tell you all about how they think we’re actually living in a simulation (a real example from my own dating life, lol).

So what’s my advice? If you’re interested in finding a long-term partner, look for friendship first, not necessarily fireworks. Don’t expect people you meet online to be so intoxicatingly interesting on a first or second date, unless you’re looking for a quick one-nighter, then obviously that’s probably something you should actively look for. I think that the kind of people who are in it for the long haul are probably not going to shower you with passion, intrigue, and hot, hot chemistry on a first date. They may be looking for a vibe check and deciding if they actually like hanging out with you, while you may secretly have the expectation that you’re going to be immediately whisked off your feet; something that feels a little more akin to a romance novel than real life.

When I started really drilling into what I actually want and need in a long-term partner this time around and how I would “filter” men I saw on dating apps, one thing stood out to me more than anything: I need a partner who can keep up with me. My brain moves a mile a minute and I can be quite a chatty Cathy if you get me going, so quality of conversation is the number one thing I was looking for. This is (obviously) wildy incorrect, but for a majority of my time in the world of online dating, I usually “filtered out” men who didn’t go to college. I grew up in a house full of overachievers, in an environment where going to college was the only option presented to me, so dating someone who also went to college also felt like my only option. Over time, though, I realized that going to college isn’t even remotely related to finding the connection I was looking for. So when the most stimulating conversation - by far - with a guy on a dating app came from someone who never went to college and I wasn't 100% sure what he even looked like based on the insane variance in his pictures, I said: “Who cares???” Paul presented as a little outside of what I thought was “my type” when we were chatting on Hinge, but the conversation we were having was light years beyond any others I had going with a few other college-educated, “good on paper” guys. Our “second date” was a six hour Zoom call with zero distractions and one bathroom break that only stopped because it was 3:00am his time and I made him go to bed. And the rest, as they say, is history.

What I mean by all this is: Don’t draw conclusions that don’t actually mean anything when you’re filtering through people on dating apps, and don’t be afraid to turn the locus of control onto yourself and your unintentionally homogeneous (or stupid) swiping behavior. If you’re bored by everyone so far and want an interesting weirdo, choose the person who has a photo of themselves presenting their prize-winning taxidermy collection; not the 37th blandie you’ve seen this week posing next to an elephant or large fish of some kind (IYKYK). Step outside the box a little and consider what type of people you’re swiping right on and setting up dates with. If something continually isn’t working with “your type”, try something totally different. Pay closer attention to the conversation you’re having with someone than to their photos (unless they have a shirtless mirror selfie… ew). Some portion of the people we get excited about on dating apps are fake profiles–either catfishers or bots–designed to attract people (have you seen the Tinder Swindler documentary?!?). You might be swiping left on people who would be perfect for you IRL because scammers are making them look less desirable in comparison. Just something to keep in mind next time you’re about to pass on a profile in favor of one that appears a little sparklier on a 6x3 inch screen. My partner’s profile was pretty boring, honestly, yet he’s one of the most wonderfully weird and complex men I’ve ever met.

If the dates themselves are getting stale and you’re not having fun anymore, suggest something more unusual like mini golfing, a donut tasting, or an amusement park. I did an escape room on a first date with a vegetable-hating aerospace engineer who was far too introverted and stubborn for me, but the date itself was actually one of the most fun I’ve ever been on. There wasn’t a second date, but the next time an escape room opportunity came up, I was first in line.

x Kelly


Hi Kelly! I turned 25 earlier this year, and I am coming to realize that my friend group and I have different priorities and it may be time to part ways. I changed career paths at the beginning of last summer, which has been very fulfilling but has meant that I am spending more time and energy on my work. When I do have time to hang out with my friends, I find that my mostly-empty cup is left even more drained. I often feel alone or isolated, even in large group situations. Most of my friends and I have been very close since our freshman year of college, and the idea of parting ways with them breaks my heart. I understand that this is something a lot of people go through in their twenties, but I am really struggling with the decision to move on. Starting from square one and trying to find a whole new group of friends seems so scary, and some days it just feels easier to stay. How do I find the courage to move on and make new friends? – Shy Twenty-Something

Dear Shy,

My HEART!! You remind me so much of a tender 25-year-old me, with one major difference. I moved to California right after college and had a sort of forced separation with my best friends back in Colorado that made it obvious I needed to find a new friend group. My “breakup” with my college friends didn’t come until much later, and I’m actually still struggling with it as well. Losing friends never really gets easier, but I can promise you that your time is better spent with people who “fill your cup.”

What I don’t think many people realize is that friend breakups can be just as devastating as romantic uncouplings. A majority of people who want a romantic relationship are looking for just one partner, which in a way makes it somewhat easier to understand why someone might not be “the one.” With friendships, though, there is a technically unlimited amount of friends one person can have, so cutting off a friendship feels less understandable than leaving a romantic relationship that just isn’t right. But like in romantic partnerships, having different priorities than your friends or imbalances in what you want out of a friendship is something that can happen, and it can feel devastating. In my mid-twenties, I was friends with someone who didn’t want as close of a friendship with me as I wanted with her, which I slowly realized over time. It wasn’t a breakup, but I had to accept that I needed to take an emotional step back from the relationship, even if I didn’t want to. I went from calling this person my best friend to accepting that I wasn’t in her “inner-circle” over the course of a few years. I finally made my peace with it, and I’m so happy that we’re still good friends to this day. Just not like when we were younger.

Your twenties are a time for personal growth and discovery, so it sounds to me like you’re well on the right track. You may find relationships in your twenties (both romantic and otherwise) that will last a lifetime, but you certainly will have time for that in any future decade of your life, too. I don’t know what kinds of differences or conflicts have happened with your college friends that have led you to feeling like you’re at this fork in the road, but it’s completely okay to find yourself in a different place in life than you were when you developed these friendships at 18. I remember thinking when I passed my 10-year college reunion (which I didn’t attend) that it was truly incredible how everyone’s lives had taken such different, unique paths. Someone who feels like a sister at 22 can be more akin to a stranger at 32. It’s not easy, but it’s life.

Let me tell you a little bit about what being 25 and starting over with a new friend group was like for me. I had been living in Los Angeles for three years and had just a handful of friends, all of whom I knew prior to living in LA or I had been introduced to by a mutual friend. We were all incredibly busy with our jobs, and worked in very different industries. After what felt like an Earth-shattering breakup, I was getting close to giving up on LA altogether and heading back to Colorado or the Midwest. I missed the closeness I had with my college friends and was often really lonely–but loved my job. The one thing missing in my life was a larger group of friends, I just wasn’t sure how to find it.

Enter my friend Noelle, a tiny, hilarious extrovert who I met a few weeks after moving to LA in an improv comedy class I decided to take on a whim. We were friends for a few years (we went to the Cheesecake Factory like four times a year, because we’re cool like that) but never hung out in a real way until three years later. She randomly called one day (I thought to make plans for strawberry cheesecake) but instead of a dinner date, she was looking for another woman to join her kickball team. I had never played kickball before, but I said “why not!”. This kickball team ended up being a major reason I stayed in LA for another seven years.

About halfway through my time in California, I decided to go to grad school. I met two women there who I love and will be friends with forever. One of these friendships was forged literally on the first day of orientation, but the other took more time to cultivate. She and I hit it off right away, but were both super busy trying to manage it all. A few years after grad school was over, we both found ourselves in similar situations–she was going through a divorce, and I was healing from a failed engagement– and we leaned on each other. I hate the circumstances that brought us together again, but the outcome was a super rare forever friendship that won’t end just because I moved to Minnesota.

My best advice for someone in your position is to get out there and pay close attention to connections you make with people you enjoy spending time with, and give those connections some time to flourish. Looking back on it all, I can confidently say that true connections happen more easily than you might think when you’re bold enough to put yourself out there. Just give your new friendships some time to blossom, and I think you may be pleasantly surprised. Join an intramural sport. Sign up for a flower-arranging class. Take a course at a nearby college in a subject you’re interested in. The people who have become my best friends have pretty much all come from taking some kind of leap into something brand new and really having that work out for me in the long run. (Although I found my best friend Jessica Kane in 2018 because I slid into her professional DMs to convince her to apply for a job opening–that was just luck. Or was it?!).

I encourage you to think of your current situation not as trading one friend group for another or starting over from square one. Rather, focus on putting yourself out there and the connections you make while you’re out in the world having fun, and let life take its course. Becoming closer with the people you’re meant to be close friends with will happen naturally, and other relationships will fall away. Unless your friends have done something you consider to be unforgivable or egregious, I don’t think a “breakup” is necessary. Spending less time with them and letting those relationships fade naturally is totally normal. Enjoy the rest of your twenties, and remember that life in this era shouldn’t just be about work. Take the trip, do the project, say yes to something scary. Good luck!

x Kelly


My friends and I are all in the same age and stage (late 20s/early 30s, single, career driven, living in LA). I can personally attest they're as beautiful on the outside as they are on the inside and not one of them can find a guy. They've tried friend set-ups, dating within social groups, going out at night, group activities and dating apps. Nothing has worked for any of them. I'm at a loss as to how to help them and myself, but we're all burnt out and it seems like dating is dead. Did 2020 kill dating? I will add: My last date was with a lawyer who brought a cat on a leash–I think that was the straw that broke the camel's back. ;) –Christine

Dear Christine,

Men are trash!!!! I’m kidding. Or am I… Honestly I’ve lived through what you’re saying, so I’m not going to sit here at my keyboard and tell you that you’re totally wrong. Dating in our modern era is certainly different than it has been at really any point in history. In the past few decades, not only have 39% of heterosexual couples found their partners on dating sites (which was a whopping 0% when our parents’ generation got married), but it’s also another vibe entirely to date after/during Covid and when we’re possibly on the brink of World War III.

Let me just say that, firstly, I’m pretty confident the problem isn’t with you or any of your friends. You all sound like fabulous people who have actually been trying your best to meet a partner. You’re all putting yourselves out there exactly in the ways you should be, and you still can’t find the right match. Trust me when I say I know how frustrated you are! I’ve been there! I lived it!

Last summer I was venting these same frustrations to my friend Karli, who met her husband on Tinder in 2014 in Los Angeles. Mike isn’t a lawyer with a cat on a leash, but he is a finance guy with an in-your-face personality and a mild case of narcolepsy (and one of the best guys I know). Karli is an absolute catch with an equally strong personality, and somehow they’re perfect together. Their first date was right after she went to a workout class to get milkshakes (hers raspberry, his strawberry) and he is still in her phone as “Strawberry Mike.” People like Mike eight years ago exist in Los Angeles, but unfortunately I think they’re pretty rare. I dated for 10 years in LA and walked away with a small rolodex of exes (including one of Mike’s friends, haha) and that was before Covid entered our lives. So did 2020 break dating? I’m not sure. I think dating in a big city like LA might have already been hard before we were all locked inside with our feelings for over a year.

I could write a long essay about why you don’t need a partner to be happy (you don’t!), but reading your question again, you don’t seem to be writing from a place of desperation or sadness, so I’ll skip it. Instead I’ll leave you with this piece of advice that I learned from my high school chemistry class. If you’re running an experiment, try changing one variable at a time and repeat until you find success. You’ve already tried changing your method of meeting people, so that’s out (but I think probably still a good idea to keep trying, either way). You’ve probably already tried changing what kinds of people you’re swiping on or choosing to walk up to at a bar, so that’s probably not it either.

Have you ever considered that Los Angeles might be the variable that needs changing in the experiment that is your love life? As I vented to Karli about 10 years of dating in the same city and never really getting the desired result, she had an idea: Why don’t I try dating in Minneapolis? I was heading home to see family a few weeks after we met up, so she suggested downloading Hinge while I was there and chatting people up. At first I thought “well that’s such a Karli thing to suggest” (she’s a much bigger extrovert than I am), but then I decided–why not?? I planned to do two weeks of “research” into the Minneapolis dating market while I was home, just to test the theory that Los Angeles was at least partially to blame for why I wasn’t finding the right partner. I have just moved across the country and now cohabitate with the man I met during this experiment, so I’d consider it an incredible success!!!

Dating long distance isn’t for everyone, but boy is it easier now that we’re so used to Zoom meetings at work and FaceTime hangouts with friends. If there’s one good thing that has come out of this pandemic, maybe it’s that we can now feel confident expanding our dating pools outside the cities we currently live in. I’m not saying that you should up and move to a new city in the pursuit of love, but I’m not not saying that either. If you want a partner and can’t find one, all I have to say is just try everything. Keep your options open… it certainly worked for me. Maybe your question to me next year will be how to convince the person you love to move to Los Angeles, or how to make friends in a new city… you never know!

x Kelly

P.S. My friend Caitlin found her husband by walking up to him in a bar in Los Angeles (after making eye contact with him all night) and asking if he was really going to leave without her phone number. So if all else fails, don’t forget that fortune favors the brave!

Have a question for me? Submit it right here, and I’ll see you next month.

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