Reading Logan Ury’s book, How Not to Die Alone, was a transformative experience for me. For once, I didn’t feel like I was weird for finding online dating so hard. She says in the book that yes, it is hard to date in this modern era of dating apps. It’s an entirely new experience from the way we evolved to find a partner (typically, the person in your neighborhood) and there are so many options (both with partners and with dating apps) these days. It’s hard to stand out and hard to take things from the phone screen to real life. Even more, meeting someone IRL is damn near impossible. Where is my adorable meet-cute in the fiction section of my favorite indie bookstore?! I know way more couples my age that met through dating apps than met IRL. Even my mom and stepdad met on a dating app!
I learned a lot from this book: how to set up a dating profile, how to make conversation over a dating app, how to set yourself up for success when it comes to first dates, and more. I learned so much that I developed a few new rules for dating that I plan on implementing in my dating life going forward:
1) Make sure every prompt on my profile is a “conversation starter.” This was a really good tip from the book, about making sure your profile has information that could be a good launching point for a conversation. It’s always so much easier to start a conversation with someone from a dating app when they have something interesting on their profile! Right now, I mainly use Hinge and Bumble and these apps use prompts to help foster communication between matches. I just need to make sure all of the prompts I have on my profile could lead to fun follow-up questions. Like, instead of saying, “What I’m looking for in a future partner is… someone kind and funny,” I could say, “What I’m looking for in a future partner is… someone who will willingly explore a bookstore with me.” Or something like that; something that just has a bit more personality and explains who I am.
2) Have a handful of opening lines to use. The opening line of a conversation is the hardest thing for me! Do you know how many times I’ve Googled, “best conversation starters for Bumble”? Too many to count. When there aren’t any interesting questions to ask based on the profile, I want to have a few opening lines in my back pocket to start the conversation with, rather than the lame “Hey! How is your day going?” Something like:
- What’s something you’ve always wanted to learn to do?
- What’s the last great book you read? (<– This one always makes me sad, though, because it feels like nobody reads anymore, ugh.)
- What’s your favorite spot around town to spend a Saturday morning?
If you guys have any better opening lines, PLEASE LET ME KNOW. I am not great at coming up with my own. I want something that would be fun to answer, but also tells me a little more about their personality.
(I should mention that Bumble/Hinge also have a “question” feature where you can pick a question from a random list and both of you answer it. Sometimes I use that feature, but sometimes I feel really lazy about using it rather than asking a question on my own.)
3) Set aside time at least twice a day to swipe/respond to messages. I am terrible at keeping up with my dating apps. It just feels like so much work that sometimes, I’ll start a conversation with someone and then forget to open my dating app for a week. (Can you see why I needed this book?!) Thankfully, Ury doesn’t think you need to spend all day on your dating apps, but she does note that you should set aside time every day to swipe and respond to messages. I think I will set aside 10 minutes in the afternoon and 10 minutes in the evening for this. It can be something I do while reading on the couch or watching TV, and if I’m not actively messaging with anyone, I don’t need to spend, like, a full 10 minutes swiping (or I could use the time to update my photos, answer a new prompt, etc.). What I need is to schedule it into my day so I don’t go 3 days between messages (which is what just happened with someone I was messaging with, oops).
4) Set dates within 72 hours of messaging. Oh, setting that dreaded first date. I used to get so caught up in textual relationships—a relationship that mainly happens over text and dating app messages. I’ve gotten better about it. Once we’ve exchanged a few messages and things seem to be going well, I’ll propose meeting up for a coffee date.
5) Have a pre-date ritual. Before one first date I had, I put on my makeup while leaving a Marco Polo video for Mikaela, and that was such a lovely way for me to get excited about the date. I talked to her about the person I was going out with and what I was hoping for from the date, and that memory holds a special place in my heart. The book recommends that all daters have a pre-date ritual to put yourself in the right headspace. You shouldn’t be rushing out to the date in between work meetings or after a sweaty workout. Make it special! Maybe it’s doing a 10-minute meditation, or chatting on the phone with a friend, or drinking a small glass of wine beforehand to loosen you up. For me, I think I’ll probably continue doing these Marco Polo videos for Mikaela before each date. She’s someone who is always excited to hear about my dating life (without making me feel like I must go on dates and put myself out there), and it makes me feel a little less alone in this journey.
6) Have a go-to first date spot. One of my least favorite parts of dating is choosing that first date spot. Do we do dinner or a drink? A coffee shop or a bar? Do we meet in the middle or close to one of our homes? What’s the parking situation like? Should I Uber there or not? So many decisions before you ever get to that first date! That’s why I love this idea: just choose your first date spot and stick with it. I’ll probably need to find two first date spots: one near me in St. Petersburg and one in Tampa (at least with the men I’ve dated, if they live in Tampa, they do not want to come to St. Pete for a first date). But that way, I know exactly where I’m going, how long it takes to drive there, what the parking situation is, what the seating is like, and what to order. As someone with social anxiety, which makes dating 1000x harder, this is something that gives me a little slice of comfort before something as scary as a first date.
7) Have a debrief after the date. I loved this idea from the book of checking in with yourself after the date. Ury lays out a handful of questions to ask yourself so you can better understand how you really felt about the person you just went out with:
- What side of me did they bring out?
- How did my body feel during the date? Stiff, relaxed, or something in between?
- Do I feel more energized or de-energized than I did before the date?
- Is there something about them I’m curious about?
- Did they make me laugh?
- Did I feel heard?
- Did I feel attractive in their presence?
- Did I feel captivated, bored, or something in between?
In the book, Ury says that knowing you have these questions to answer after the date makes you more aware of how you’re feeling during the date. I am someone who is always fairly aware of how I’m feeling, especially whether someone is making me feel comfortable and relaxed or insecure and awkward. And this checklist focuses less on how the person looked and acted and what they said, and more on how I felt on the date. Even if it’s someone who checks all of my boxes, if I felt uncomfortable during the date, then that’s what I need to pay attention to.
8) Always say yes to a second date. I’ll admit that I am an all-or-nothing girl when it comes to dating. If I don’t feel that spark on the first date, I’m not going on the second date. It’s either there or it isn’t, but Ury stresses in the book that we should always say yes to a second date, even if the first one wasn’t that great. (Of course, if the person made rude comments or made you feel uncomfortable in any way, you do not owe anyone a second date!) But if it was just a lackluster first date, what’s the harm in giving it another shot with a second date? Maybe they were nervous or had a bad day or were distracted for some reason. This will be a hard rule for me to follow because I have limited energy levels and it’s difficult for me to keep going on dates with someone I’m not super excited about, but I’m going to give it a try and see how things go.
***
If this feels like a lot of work, hello, welcome to dating. It is a lot of work and that’s why I go through long periods of not dating. Putting in so much effort with the chance that it can be all for naught is one of the reasons I haven’t ever fully invested myself in the dating process. Add to the fact that I’m an introvert with social anxiety and sometimes dating feels like an insurmontable task, based on how I’m feeling on a particular day. But I do it because of the times when it has worked for me. When I have found someone I click with on such a deep level that they’re all I can think about. I do it for the butterflies, the anticipation, the way it feels to fall head over heels for someone. I do it because I want to find my person and I truly believe they are out there.
This is a great list! I am so so glad that book was so helpful. And I believe your person is out there too.
I really like the idea of putting things in your profile that lead to conversations. And I hope some of your opening questions could be based on their profile! But hit your girl up if you need ideas – all I do is talk to people and I can talk forever and ask a ton of questions 😉
You are great at asking really good questions – that’s something I appreciate about you (among many other things!) The next time I’m stumped on how to start a message, I’m coming to you!
I’m a huge fan of online dating because that’s how I met my husband! Yes it’s overwhelming but the payoff is well worth it. My best advice to anyone is to just try it and yes it’s OK to take breaks when things get overwhelming. At one point I took a one-week break and left my now-husband/then-internet stranger hanging in the middle of a conversation. When I came back I just told him that I was new to online dating and had gotten freaked out and he said that he could relate.
I strongly agree with meeting IRL sooner rather than later and I also think that the book question is a good screening tool. I’ve always had bad luck dating non-readers. My husband listed the last great book that he read in his profile which was one of the many reasons why he stood out to me in the online dating sea;-)
That is such a sweet story about how you met your husband! It seemed like it was meant to be if he stuck around even after you took your break! 🙂
I have not dated in decades, so I have nothing relevant – it’s a different world out there. But here are some life lessons.
1) When we write survey questions, it’s actually easier to ask people for a specific action they’ve completed, rather than to talk about general past behavior. So, instead of asking what’s your favorite X, what’s the last X you did. So, I don’t ask what’s your favorite book, but what’s the last book you read? What’s the last television show you listened to? The last song/podcast you listened to? The last workout you did? So, I would probably lean towards those types of questions as conversation starters. Yes, I just listened to a song by Taylor Swift. It’s not my favorite, but it came up on my Spotify list. I prefer country Taylor to pop Taylor. There’s lots of places that conversation can go, regardless if someone liked the last thing they did or not.
2) I was not convinced that I was physically attracted to my (now) husband until like the fifth date. I really liked him and thought he was hilarious, but the physical spark took some time. Now I think he’s the best, but I think that if you like someone’s personality, the physical stuff can find a way. I think it’s probably smart to give people a chance. There are only so many nice folks out there!
3) Good luck with dating. It’s hard out there!
This is such great advice, NGS! I really appreciate you breaking this down for me, especially the better way to ask questions. I really like the idea of just asking what was the last show they watched or song they listened to – an easy one to answer and, in some cases, can lead to a fun convo!
Even though I’ve been out of the dating game for many, many years, this is all very interesting to me. I didn’t know these dating apps even have “question” features. In a lot of ways it seems kind of ridiculous- but I know it works. Two of my close friends started dating again after getting divorced, and both found their new partners using a dating app, so…. it’s definitely the way to meet people.
Brilliant idea for a book, and it sounds like the suggestions will be really helpful. You’ll have to keep us updated on how it all goes!
I’m now more surprised if I found out people met IRL than I do if they met through a dating app. That’s where it’s at these days.
This book sounds really great! Another question you could ask if what was your last vacation or your favorite vacation or something along those lines? Kind of gives you an idea of what a person is drawn to.
I was on and off dating sites in my 20s/30s. I mostly used Match and then before I met Phil, I was on okcupid for about a month. I tried to arrange a date asap because you can trick yourself into thinking you have chemistry with a person over text but then in person there is no chemistry. I would have a hard time with the 2nd date rule, though. I felt like the more I saw a person, the harder it was to break things off so I’d err on not going on a second date if I questioned things at all. But I lucked out and met Phil through a blind date and there was an instant connection. I went home from the date and closed my okcupid account. I was so sure I was going to end up meeting someone online, though! I really tried my best to meet people naturally – like I joined running with a secondary reason of maybe meeting another runner. And I did a speed dating event once which was awful honestly!
That’s a great opening question!
I am someone who usually has instant connection with someone than not, and usually it’s very hard for me to commit to that second date if I’m not TOTALLY sure something is there. But I could also be missing out if I’m so quick to turn down that second date… I just won’t know unless I make it a rule. We’ll see if it ends up being a good or bad idea!
This was so fun to read! Such great tips!
I recently read an article (I think???) about the best question to ask instead of small talk, and it was something like, “What’s a secret you know that no one else does?” I also like Lisa’s suggestion about travel related topics! Since you are such a traveler, you could ask about what travel destination is on their bucket list. Or maybe… who are their auto-buy authors.
Oooh, that secret question is such a good one! Could lead to a really fun conversation. Thank you for that!
It’s not related to this post, but: I listened to your first podcast episode yesterday and really enjoyed it! You and your friend Briana (not sure how to spell her name) have lovely voices and a great rapport! I listen to podcasts constantly and know when a pair has “it,” and I think you two do! 🙂
I liked how you bantered and also gave the surfacey-deep-dive lesson on Meyers-Briggs. It was neat to hear you both explain who you are and about how you identify, personality-wise. I took the test you linked to and got INTJ—the one you described as Dwight Schrute. Oh no! I really don’t think I’m arrogant or combative, but a lot of the other things jived. I took a different one and got INFJ, which rang a little truer, maybe (?).
Anyway, it was fun, and I’m looking forward to the next episode! And the Harry Potter house talk, whenever you get to that!
This is the sweetest comment and it really brightened my day. Thank you so much!
That’s interesting that you tested as INTJ and then INFJ – seems like the I, N, and J are accurate but you can switch from Thinking to Feeling depending on the circumstances! INTJs are very wonderful people, so don’t get too bogged down in the Dwight Schrute reference. You are bold and rational and independent and aren’t afraid to take risks. It’s mostly that you aren’t as motivated by your emotions as other people, but that’s not necessarily a bad thing!
This is so interesting to me! I met my husband in 1996 and we started dating in 1998. At the time there may have been dating websites, but I didn’t know about them, and in any case, they would have been very new. I mean, EMAIL was new back then. At that time the way you met other people was through work or school, at the bar, or through mutual friends. I think this is just fascinating, how it happens now!
On another note, I listened to your podcast yesterday and I really enjoyed it! I always hear people talk about Myers-Briggs, but I didn’t know anything about it. I have taken the test – years ago – but immediately forgot what I was. Maybe I’ll take the test again! Although – and this is going to sound silly – I am a real astrology girl. I think people’s personalities are often reflected by their astrological sign! I hope you do an episode on that!
I would imagine dating websites in the 90s would have been such a weird way to meet someone! I feel like it was still weird until maybe in the last decade or so, when we all became Very Online.
We have an astrology episode coming up! But I am soooo not into astrology (I’m a Sagittarius and the complete opposite of that sign!) so it’s something that doesn’t really make sense to me. But I know a lot of people really feel tied to their astrological sign!
Thanks for the book recap!
I agree, opening lines are super hard! Perhaps share a fun/silly photo of yourself to and tie that in with your opening line. This worked well for me: I had a Halloween costume (Mrs. Incredible!) as my main photo and used that as a fun conversation opener. And almost everyone who messaged me first used that as an opener, too! The conversations that stemmed from that were great: back-and-forth about Pixar movies, things we like to do for fun, career ambitions (stemming from a conversation about superpowers), technology/biomaterials (stemming from a conversation about Elastigirl’s elasticity, haha).
I like the idea of having a pre-date ritual! And of course, you are not alone in this journey! I recently discovered Finding Mr. Height on Instagram. She films herself getting ready to go on dates and I love watching her do the most mundane tasks like putting on makeup, haha. What I learned most from her is to just enjoy the process!
“Just enjoy the process” – yes! That’s what I really want to learn to do when it comes to my dating life. I’ve been so crazed about finding my forever love that I’m not enjoying just the simple fact of meeting new people, getting to be romanced, getting dressed up, etc. I want it to be more enjoyable!
Wow, I am like … shocked… how much work goes into dating these days. I feel very inexperienced in a lot of ways. I never officially “dated” (I met both my partners – my ex-boyfriend (in Germany and my (now) husband – generically and the relationships also developed naturally. There was no Facebook, Instagram, or any dating app.
There also was no “dating” in the sense of what it means today. We hung out for a while casually and things developed from there. I never thought of it as “actively dating” and thinking about if there was going a second date or not .I would fail miserably (I think) if I had to date in the modern world. I do not envy you… but I think it’s great how you’re seeking out strategies and advice to make this a more pleasant experience.
Finding new people is hard. The closest I’ve come to “dating” is trying to make new friends (and we all know how exhausting that can be without the add-on pressure of physical attraction) .
Trying to make new friends often feels a LOT like dating! I mean, Bumble even added it as an option on their app (Bumble BFF, where you can set up friend dates!). So you’ve gotten to see just a little bit of what it’s like to be dating in this modern era, haha. 🙂
Wow, this was so interesting to read. As you know, I have no interest in dating (although definitely interested in trying to make some friends…) and this, well, it just makes me less likely to think about it! This whole process must be so stressful… wow. But, I LOVE the idea of focusing on how they made you feel – and how your body reacted. Those visceral reactions are SO important!
I think your approach is really excellent, and I’m wondering if, in the time since you’ve implemented it, you’ve noticed a difference in either how you feel when you’re using the apps, or how things are going when you do get a match? Or has it been too short a time to see any, um, results(?) yet?
I would love it if you periodically updated us (ha) on how things are going but also completely understand if you want to keep things private. 🙂
Ugh, well, I tried going on two dates with two different people and BOTH of them canceled on me the day of the date. It has been very frustrating and I haven’t been very active on the apps since then. So blah. Dating is very annoying and I completely understand not feeling the urge to even consider it.
Wow, that is a lot of work! I agree with the second date rule, as long as the person wasn’t an ass or something. My husband and I met (before you were born probably) in 1987, and the first time we went out we liked each other well enough in a friendly way, but there wasn’t really a spark. We went again, and that time we had sparks, we ended up talking until 4am. We consider that our first date, though perhaps that is revisionist history.
Our daughter dates using an app, and it has not been great. I think it’s hard on a person’s self esteem, and it can be demoralizing and tiring. I wish it were easier to meet people more organically.