Relationships

Dating for the First Time in Six Years

Dating for the First Time in Six Years

This spring, our series of personal essays is all about dating. Each contributing writer will share a true story, from texting to sex to breakups. Today, Emily Johnson talks about taking a six-year hiatus from dating and how she broke the ice…


When I moved to New York City for college, I had seen every episode of Sex and the City approximately 200 million times. I knew the show was fantasy, but a small part of me hoped that in New York I’d lead the kind of adventurous dating lives its characters did. Instead, I spent my first year pacing the fluorescent-lit halls of my dorm, making tearful, jealous phone calls to my high school boyfriend in California.

When that relationship ended, I realized I had behaved like a crazy person. I wasn’t confident — in my body, mostly — but also that I was interesting or smart, or someone worth dating. I didn’t like that I had made someone else responsible for buoying me up. It wasn’t fun for me to be insecure, and it was miserable for him. I vowed not to date again until I could be the kind of confident person someone could love without so much burden.

This is how I started playing the game of, I Won’t Start Dating Until… You know, like, “I won’t start dating until I’ve lost 10 pounds.” “I won’t start dating until this large zit has disappeared from my face.” “I won’t start dating until I have my dream job.” “I won’t start dating until I am completely up to date on current world affairs and have read the entire published works of Proust.” I knew I should focus on simply becoming more confident, but I couldn’t help but persist in the flawed line of thinking, If I can just improve myself, I will naturally become more confident.

And so, in a flurry of books and movies and new friends and parties and promotions and lovely time spent with family and trips abroad, somehow six whole years passed and I’d never had a boyfriend, or even really tried to date.


Then, a funny thing happened. Cup of Jo asked me to contribute to this new dating series. I almost laughed out loud at the idea — asking me to write about dating would be like asking Carrie Bradshaw to write a regular column for Popular Mechanics. Still, I thought, I’ll do anything for work. And if I was going to write a story about dating, I would have to go on a date.

“It’s like How To Lose a Guy in 10 Days,” a coworker said in excitement. “This is totally going to be how you meet your husband.” Another colleague overheard and nodded. “I’d definitely watch a gritty reboot of Sex and the City with you as the star,” she said. Or Sexless and the Outer Boroughs, where an anxious girl has so much body insecurity she can hardly wear a bathing suit in front of friends.

I called in some friends to help construct my online dating profile, trusting them to serve as impartial judges. (I figured you don’t want a profile photo that’s too good and doesn’t look like you, but you also don’t want to choose a horrendous photo of yourself!) Over a round of drinks, they picked pictures that they assured me represented what I actually looked like. Then they took the reins and started swiping. This culminated in a physical tug of war in the middle of an East Village dive bar, the object of which was my phone. “You have horrible taste!” one of my friends yelled at the other, “She’d never go on a date with that guy!” After things got physical, I took my destiny back in my own hands, or rather, my own finger swipes.

Now I’ll tell you what you likely already know: It’s extremely easy to get a date as woman on a dating app. After six years of feeling hideous and insecure, in a matter of minutes I had as many potential suitors as Nick Viall on Episode 1 of this season’s Bachelor.

The only problem was facing one of them in person. After sending 20 or so “Describe yourself as a cocktail” or “What’s your favorite restaurant in New York?” cringe-worthy ice breakers out into the Bumble ether, I racked up the courage to ask one of them on a date. He’d been easy to talk to. He was cute, but not so cute he was intimidating. We scheduled a date for the following Saturday. I suggested early evening drinks to eliminate some of the pressure of a Saturday get-together and to test the waters before committing to dinner.

There was outfit deliberating. I considered going shopping, but procrastinated. Two friends, completely independently of one another, said, “Just don’t wear a vest.” (Okay, I wasn’t aware that I wore vests that often?) In the end, I wore black.

I walked to the date spot and called my mom on the way, shaky hands gripping the phone to my ear. Standing across the street, lingering on the sound of my mom’s voice uttering the last few words of a pep talk, I saw him arrive. He was wearing a faded jean jacket and looked nice — and much more relaxed than I felt.

And the truth is, after all of that, the date just… wasn’t a big deal. In a good way. I approached him at the bar. He bought the first round. The conversation flowed relatively freely. He was easy to be around. I laughed and he laughed. I bought a second round of drinks and the ease of being together continued. We talked about restaurants, our jobs, college basketball, our families, where we grew up and where we’d like to live. It was totally fine — an enjoyable, if unremarkable, way to spend the evening.

He asked if I wanted to get dinner. We walked next door to a Vietnamese restaurant and I made an embarrassing suggestion that we share a bowl of pho. “I don’t think we’re at the soup-sharing stage of our relationship,” he said. I laughed, but I had a flash of longing for my best friend — the comfort of eating with someone who shares all of my favorite foods, who always wants to split two dishes so we can try more things.

Even so, as we slurped our individual bowls of noodles, I enjoyed the company of a new person, someone whose favorite movie I didn’t yet know, whose preference for cake donuts versus yeast donuts was a mystery as vast as the universe. It wasn’t a soulmate, love-at-first-sight situation. I wasn’t Kate Hudson and I didn’t meet my future husband. I wouldn’t leave buzzing with excitement on the walk home, but I would leave proud that I had ripped the Band-Aid off and it was relatively painless. Dating, in the end, is an opportunity to have new conversations, see fresh perspectives, dine with someone with whom you wouldn’t yet share soup. At the end of the night, in front of the restaurant, we hugged and he suggested we get drinks later that week.

And, I think I will.


Emily Johnson is an editorial assistant at Lucky Peach, where she repeatedly microwaves cups of coffee that have gone cold on her desk. She lives in Brooklyn with her fish, Moby. You can follow her on Instagram, if you’d like.

PS. “My boyfriend weighs less than I do,” and how to know if your partner is The One.

(Illustration by Alessandra Olanow for Cup of Jo.)

  1. Bravo, babe! Dating is hard! I left my partner of eight years when I was 28 years old, and it took me quite a while, now 32, to earn my confidence.

  2. Rue says...

    Just started dating about 6 months ago, and dove into online dating 3 months ago. It’s not my favorite thing, and it requires a LOT of bravery, but I do think the silver lining is that you learn a lot about yourself. I’m realizing I had lots of ideas about what I wanted — both in another person and in the structure of dates or relationships — that came from places other than ME (so family, friends, society, etc) and were things I had never examined. Finally dating for the first time at 30 (having spent my 20s in long term relationships that were serious commitments from day 1) is helping me see what ideas about myself and relationships are things that I can let go of. It’s kind of amazing, even though it’s time consuming and emotionally taxing.

  3. Mandy says...

    I met my husband on Match. He was the first guy I dated online in my current city (lots of frogs in prior city).
    Our first date featured a lot of fun conversation, a few awkward moments (me eating off his plate and somehow telling our server not to offer us drinks?!?!?!?!), and very little chemistry. The next date was better, the one after was on fire, and less than three years later we have a 4 month old baby. I wasn’t sure I wanted to get married OR have kids! He’s the best guy I’ve ever dated by far, with amazing family and friends that didn’t show through on his online profile. We drive each other nuts too, in ways we both can tolerate so far.

    Also, nothing has been better for my body-confidence than an all-inclusive resort in Mexico. I realized: everyone else is just fine! And some of them are wearing the craziest shit! I am just fine! My “bikini body” policy is just as strict as it once was, but in the opposite extreme. Find a body. Put a bikini on it.

    Good luck! I really enjoyed your article. Can’t wait to read the comments.

    • Rue says...

      Thanks for sharing your story! Perfect timing, because I just had a first date that was good but I was secretly expecting more sparks. I’m hoping we build from here, because he seems like he could really be a great fit. I have to remember that putting a lot of expectations on a stranger is just unhelpful for both people involved!

    • Agnes says...

      Totally agree!! I’ve been dating an amazing guy for 3 months now, however the first blind date (set up by my sister!) was a little awkward. We were both nervous and had such high hopes. We ended up laughing at ourselves and how awkward we both were and continue to be, haha. It takes time to get to know people, so if the bare bones are there for a relationship, I’d say keep going and see what happens!

  4. I loved reading this. I have often wondered what it would be like to use dating apps, which I have never done. My boyfriend and I often say that if we were ever not together, neither of us would date anyone ever again because of how terrifying it was/is! Her mentality is right on and really inspiring not just in a “getting yourself out there” way but also just in a person-trying-new-things-way if that makes sense :)

  5. Lo says...

    Wahooooo! Go girl!

    First thing, I am superrrrr proud that you decided to throw caution to the wind and ‘do it for work’. Most people would turn down the opportunity and run for the hills. That’s so badass confidence right there, don’t beat yourself down!

    This sounded so true, I remember calling my Dad on the way to my first date after having stomach surgery (ugly scars and an ileostomy at 20) and almost being in tears. I remember him laughing down the phone at me, saying if I could bungie jump with my intestine on the outside, I could go on a date with a nice chap who knew all about the circumstances.

    Since then, I’ve accomplished a lot in the dating world and ended up buying a house with my best friend and future hubby, and I put it all down to that weird, kinda awkward date at a boat house when I was 20.

    Lo
    http://www.themixtures.com

  6. I’m 32 and recently out of a four year, live together relationship. I waited to ‘start’ dating til I was ready, and it was before I even moved out from with him, which surprised myself.

    I love getting to know new people – and it can be tiresome and lonely at times, but it can be great to find out people like you in ways ex(es) weren’t. An early date really solidified the break up and that there’s better matches out there… even if this guy inevitably didn’t feel how I did.

  7. Lina says...

    this was so reassuring for me.. i’ll be turning 22 in a week and I’ve never gone on a date with someone-even when the opportunity was there. I’m hesitant about opening up to someone romantically and i’ve been insecure all my life about being with someone *romantically*. But this gave me so much encouragement! The way I see it is if I continue on like this, years will past and I’ll end up asking why I’ve never taken the chance. Thanks for opening up to us!

    • Liss says...

      Joanna- can you maybe feature people like Lina who actually never dated etc. (“Love Aliens”). I think a lot more people are in similiar situations and would need a little reassurance that infact they are “normal” and totally likeable/dateable (if they wish to be)

    • I’m on the same page, 22 and never dated anyone (or been kissed for that matter)! I have been on a few coffee dates with guys but none of them have lead to anything.
      I do have a lot of guy friends and I hope at the right time one of those friendships might turn into something more.

  8. Such a great article! Jo, have you thought about opening up a forum for your readers to submit articles? I know you’re based in NYC but I don’t think of Cup of Jo as solely an NYC blog, and it’d be neat to read viewpoints of your readers.

  9. Maia says...

    THANK YOU SO MUCH for this article. I’ve not dates for 4 years, 3 friends announced me they’re prégnant in the past 3 weeks (have you ever cried of sadness and make it up as you’re happy when you hear about a baby on the way ? I’m always also very happy for thèm of course but sometimes couldn’t be sûre of why I was really crying).
    Well, and I’m feeling really alone with this, and because my last boyfriend died during our (half a year old but mostly happy) relationship, I’m constantly using the excuse of grief to keep myself far away from romantic life while I still long to go back in the game. Your post reminds me preciously that I’m not alone and finally just a few small steps from meeting new guys/new people!
    Also I’d be be very curious to read the dame kind of essay from a guy’s point of view!
    Bravo CupofJo for the positive impact you can have on people lives sometimes! :) (starting with Emily’s! :D)

  10. Lauren says...

    I totally relate to this and frankly felt like I was the only person in NYC who hasn’t been on a date in years and always says ‘i’ll date when…’ while all my friends are married and having kids like it’s going out of style. Thanks for making me feel not so alone.

  11. Gabrielle says...

    I never comment but I have to say I loved reading this essay. Navigating the dating world is not easy for anyone at any age. It helps to read about others’ experiences and to read the comforting, supportive comments here. I hope to see more of these touching stories! And good luck Emily, just enjoy the ride!

  12. GFY says...

    I love this! One of my favorite features is the Blind Date section of the British version of The Guardian – the paper sets up two strangers in matched pairs of all ages/races/persuasions, (much more progressive than a US paper!), sends them on a paid blind date, then publishes their responses to a quiz form – it is fun and fascinating and the couples are super brave. Even better and braver are the couples they send on first dates wearing google glasses so that we get to go on their date with them! Yikes! It’s so awkward yet heartwarming watching people navigate their vulnerabilities for all to experience together!

  13. Natalie says...

    I’m still laughing about the “don’t wear a vest” advice. HA!

  14. I loved this so much. It’s incredibly relatable, and so sweet.

  15. Cláudia Gama says...

    I haven’t dated since my boyfriend and I separated, 5 years ago. I haven’t really thought about it since this article. 5 years! A lot has happened since then, I changed jobs, I moved to another country (really very far from my homeland) and I think I didn’t have the time to think about boyfriends and dates. :)

  16. Jessica says...

    I really enjoyed reading this essay and all the comments. It’s also been years since I dated anyone, and I find it really comforting to see there’s others in the same boat. I definitely get the “I’ll date when __” as well as the wariness people mention about online dating/dating apps. I loved Sarah’s comment about resolving to go on 6 dates in a year time–for some reason, putting a number on it makes seem less overwhelming and also a lot less “I WILL MEET THE LOVE OF MY LIFE.” I mean, I’d also love to meet the love of my life someday, but baby steps.

  17. SCG says...

    I want to know what happens next!

    • Joanna Goddard says...

      i’ll ask her! :)

    • sarah says...

      Me too! Could she write a follow up?

  18. What a fun story. I feel like it’s the beginning of a book I want to keep reading. Best of luck!

  19. I loved reading this..Such an honest writing :)

  20. Nicole says...

    thoroughly enjoyed this! good luck out there emily and have fun :)

  21. E says...

    Thank you for this! I’m in the same boat, one year post-breakup. I had a few dates before I was truly ready to move on, but I enjoyed having the company. This is inspiring me to get back out there! :)

  22. Sam says...

    “I laughed, but I had a flash of longing for my best friend — the comfort of eating with someone who shares all of my favorite foods, who always wants to split two dishes so we can try more things.”

    Story of my life. All I ever want to do on dates is leave and hang out with my real friends. And I haven’t been able to get over it. It’s been 5 years since I broke up with my last serious boyfriend, though I’ve gone out with several people since then; I just can’t get myself to enjoy these people as much as I enjoy the friends I already have. It feels like I’ll never be able to love them as much as I love my friends.

    • Joanna Goddard says...

      i totally hear you, sam. i’ve felt the same way in the past. but one thing to remember is that you’re just meeting these people for the very first time, whereas your friends you’ve known forever. i really believe in the concept of FALLING in love (versus love at first sight), and it does take time. just a thought! once i had that realization personally, it helped me enjoy dating so much more. might not work for everyone, though! :)

      PS stella mentions something similar in this post about making new friends: http://cupofjo.com/2017/01/making-new-friends-as-an-adult/

    • june2 says...

      On that note I’ve heard the advice to commit to 3 dates with a new person even when you’re sure they are not a match because it allows both personalities to unfold.

  23. SP says...

    When you really enjoy the article and decide to check out the writer’s Instagram only to realize you went to high school with her!! Ha!

    • rach says...

      Hah!

  24. Why are we all so insecure?! Emily, you’re young, cute, smart, funny… it’s nuts that you’re not confident… but I do get it :-)

    I hope this project has put a little spring in your step when it comes to going on some more dates in the future. Whoever you end up with will be lucky to have found you!

    http://www.thislifeisbelle.com

  25. Holly says...

    Why do people not from New York call the other boroughs “outer boroughs”– that’s not a thing!! Awesome story though :):)

  26. Tara says...

    I’m glad you are starting a dating series as I’m thinking about getting back out there myself!

  27. Natalie says...

    “I wasn’t aware I wore that many vests”…ha ha ha ha! Loved this:)

  28. Kate says...

    I don’t usually comment, but oh man, is this familiar. After getting out out of an 8-year relationship and moving across the country how the heck does a 30-something meet new people in a new city?

    Well, you put too much creme de menthe in your hot chocolate, tipsily sign up for OkCupid, and schedule dates with 5 different guys in one week. (True story, not recommended.) The good news is, in spite of my extreme skepticism toward dating apps, date #3 was a keeper and we’ve now been dating for 4 months.

    It reminds me of a past Cup of Jo post where the advice was something like “Either he’ll like you or he won’t–just be yourself.” For me, keeping this advice in mind and approaching the experience with low (to no) expectations made the whole thing kind of fun, and you never know who’ll turn up!

    • Lindsay says...

      This is so similar to my experience! I eventually decided to carve out the time to meet people. I signed up for a free dating app and treated it like a part-time job. My friend adviced “don’t quit dating others until someone gives you a damn good reason to.” Almost one week and 4 dates in I was exhausted. But I kept my promise to myself to keep on going. And date number 5 was the dream. Everything clicked and it was obvious to us both we were meant to be in each other’s lives. 6 months later we married and 8 months later we are pregnant with our first baby. As my mom has always said, “it’s not easy to find the one, but it only takes one.” Wishing love & happiness for everyone!

    • Yes to all of it!! That is pretty much exactly what I did too….5 dates in one week (even 3 in one day once), and one of them was a total keeper :-)

  29. Sue says...

    To all of you out there agonizing about dating again after being with someone for awhile-make sure to take time to be comfortable being on your own first, and in a headspace that you are ready to move on. Make sure you have some good female friends as a support group. I’m a lot older than all of you, but my marriage fell apart after 30 years. I waited three years, then decided I wanted some male company. It took a lot of courage to go online and date again, but on the third try, I met a wonderful man. It’s been five years now, and I’m happy.

    • wb says...

      Thanks. I’m exactly one year out of a breakup (after living together) and I still don’t feel ready. Glad you rebounded!

  30. Maureen G says...

    This series is a pleasure to read. After four years as a widow (married for 22 years), my sister, who is 31 years married and a total Sex and the City fan, told me I really needed to get “out there”. I think she was expecting me to be Samantha…LOL Oh the stories and laughs we shared! Small town midwest widow on the prowl, ha! As mentioned above, it is nerve-wracking and exciting and scary and sometimes not so bad :) Having sisters and friends and a sense of humor was a must for me, especially at first. I learned so much, probably because I had no real expectations…(my sister made me go!) I did not realize what a mix of folks were out there…divorced, widowed, still married (!!) While I really did not want to “get out there”, it was good to push my comfort level just a bit.

  31. Carly says...

    Loved reading this! So fun and honest, will share with my friends who refuse to go on dating apps :)

  32. LH says...

    Just to normalize things for the girls that don’t get a ton of guys liking them on dating apps (or just in general) – I signed up on 2 apps around the beginning of the year (I’m 32 in NYC) and haven’t gotten a ton of “bites”. Mostly a handful of conversations that have fizzled. Maybe because I don’t have any pictures of me in my bathing suit? Anyway, if you have had this experience, just FYI you aren’t alone! I’ve been on one date this year and it was FINE. Not amazing, not terrible. I considered this a positive outcome.

    • SY says...

      <3 <3 <3 <3 I was looking for just this comment because I cannot. identify. atall. with the constantly reported, by my friends and strangers, "it is soooooo easy to get a ton of dates on apps as a woman in NYC" and that is just so lonely, so thank you.

    • Mandy says...

      Yes!
      My friend met her husband on Match and she said, the trick is to pick the guys and initiate conversations with them. Don’t wait for them to pick you. You find better guys this way. She also advised to go on a second date if the first one isn’t totally terrible. Because people are weird on first dates.
      The first time I followed her advice I met my husband.

    • JJ says...

      Thank you!

  33. Jade says...

    Everything in this essay rang true for me. I am 26 and have never really dated for the exact reasons above. interesting food for thought …..

  34. I wish I’d given myself that advice when I first moved to the city. I too had watched a little too much Sex and the City, and spent my first three years obsessing about boys. It took meeting my husband on OkCupid for me to actually do what you initially did. I’m now checking stuff off my reading list, learning a new language, becoming the person my husband will want to keep hanging around ;)

    That’s the nice part about marriage, hopefully you’re both up for growing and changing in sync with each other.

  35. I loved this essay! Such a fun read, thanks for sharing. :)

  36. I would totally watch Sexless and the Outer Boroughs!

    As a fellow non-dater, I’m so wildly impressed by this. Loved reading the piece!

  37. Sarah says...

    Thank you so much for this! I won’t go into details, but this is just exactly what I needed to read this week.

    Good luck, Emily!! xxx

  38. Sarah says...

    I love this piece! I am also a person who took a dating hiatus for a similar amount of time, for similar reasons. I just felt like I had lost myself and I needed to get myself back before I could date..and then there were other excuses… I finally forced myself to give online dating a serious try, and resolved myself to go on at least 6 dates that year! It took more than 6 first dates but a couple years later, I’ve just moved in with a wonderful man I met online, and I’m so excited for our future. It’s hard out there with dating, and embarrassing when so many friends (I’m 35) are married and having babies, you feel like a zoo exhibit! One thing that helped enormously was starting a text group with my other single girlfriends to bouy each other and give advice in the dating trenches!

  39. such a sweet post!

  40. I ended my 6 year relationship a few months ago. I stayed longer than I should have out of fear of not finding anyone else, and being afraid of the dating world, which I hadn’t been a part of in a long time. Once things ended, I joined Tinder to flirt and make myself feel better (don’t judge).
    Two things happened: I realized how comfortable and confident I felt in my skin at age 32 compared to the last time I was single at 26. And within 2 weeks I met a man whom I have fallen for harder than anyone before (and it’s mutual, to my great disbelief and joy). Call me crazy and naive and “this is way too soon”, but I have not felt like this about anyone in my entire life and in retrospect, I am SO glad I put myself out there and took a chance. Yes, Tinder can be a pain in the ass, but I put an honest effort into it and my world is now more beautiful than I could have ever imagined. Go all in on it all!

  41. Jessica says...

    This spoke a lot to me and hopefully will give me some confidence! I haven’t dated since gaining almost 50 pounds….and I’m terrified. I have some good conversations on dating apps, but never have the nerve to actually meet up with anyone in person. I’m convinced they’ll take one look at me and walk the other way. So I’m constantly in the mindset of I’ll start dating again when I lose 20 pounds/when I stop biting my nails/when I feel more confident, etc. But a little part of me knows I’ll just be alone forever if I follow these nagging thoughts…sigh.

    • Heather says...

      I am right there with you. I would like to lose weight, but I focus on doing that for myself, for my health. And I tell myself that if someone would only date me if I were 20, 30, 50 pounds lighter, maybe they’re not the one for me anyway.

      I also try not to overlook guys who may not be the fittest either – I’m sure overweight dudes worry about the same thing too, right?

    • Laura says...

      Also me. I’ve dated some, but I feel like I won’t find something serious until I value my worth more, and can find someone else to do the same.

  42. Marie says...

    Same story as many–long term relationship for the majority of my twenties ended abruptly and not on my terms, so once the tears slowed and my head is clearing I’m suddenly very aware that I never “learned” how to date. At the moment I’m equally terrified of being alone forever and of actually dating, so I feel stuck! And desperately wanting to avoid the online thing, since it seems like being in nyc I should be able to meet people?!

    • I was in the same stuck place for a long time. Let me tell you: you will not be alone forever. I thought the exact same thing about myself. But I ended up joining Tinder because I wasn’t meeting people on my own, and it really, really helped. Even if just to meet someone for coffee and practice my banter game. I used to think dating sites were pathetic last resorts when everything else had failed, but boy was I wrong. I encourage you: try it, put yourself out there! I met someone wonderful already, and I know you will too.

  43. Eve says...

    What a delight to read. Power to ya, Emily! I too was single for a loooong time, the whole time pining over someone I’ve magically ended up with, which made entertaining others nearly impossible. I especially resonate with this tidbit about the writer – “she repeatedly microwaves cups of coffee that have gone cold on her desk”. Ha.

  44. Laura says...

    YAAAAS to dating essays! I need to read about others’ experiences as my attempts have been less than successful. Also, Emily sounds like a lovely person and her writing was entertaining and #relatable.

  45. Andrea says...

    just emerging from a 16-year marriage which became emotionally abusive towards the end. I’m sure I’m not yet ready to look for Mr Right, partly because I still randomly cry a few times a week, partly because I no longer believe he exists. But this essay is a good shot in the arm to go practice meeting people — and to allow myself some skeptical distance while still enjoying someone’s company. Kudos to you, Emily, for getting back out there!

    • lindsey says...

      i hear you.

      i’m in the midst of a divorce too (my husband is having an affair), and i’m terrified of dating again, don’t think i could ever marry again………..i met my husband day 1 of college in 2000…..i feel like i have A LOT to learn in regards to dating. and of course, relearning how to trust someone. life isn’t for sissies, that’s for sure.

  46. I’m 21 and I have been single for about 2 years now. I have never had the mentality of “not dating until…” but it just doesn’t seem to happen to me for some reason. Maybe my introverted self is holding me back,,, I hope to go on a date sometimes soon, even just for funsies :)

  47. Stella says...

    Was this post written specifically for me?! Or by me?! Wow… I am just dipping my toes back into the dating world after 6 years, too! (Different circumstances, I got divorced and finally feel ready). So much of what you write is true! I went on my first date this past weekend and it felt so good to “get back out there” ! Was he my soul-mate? Nope. But I am so proud that I said yes to a date, felt those butterflies, was able to enjoy myself and feel so confident again.

    Timing is a wonderful thing – I cannot get over the uncanniness that THIS is the post TODAY of all days! Thank you Jo & Emily!

    Oh, and I’m about to take the Bumble-plunge too ;) Good luck to us & everyone else gettin’ back out there!

    • Joanna Goddard says...

      that’s so exciting, stella!!!! it must be a sign :)

  48. Sasha says...

    Good luck Emily!! I’m just an old married lady but I still find this stuff fascinating. Something about the idea of possibility and luck and love is just beautiful.

    • Tammy H says...

      Ditto, Sasha. And it helps that Emily is a great writer! A fun read.

  49. Michelle says...

    What a lovely essay! I can totally relate. After spending my twenties in a string of failed relationships and heartbreaks, I also gave up dating. Initially for a year, but somehow over three years later I just had my first official date since then this past Friday. I feel like I totally lucked out – not because of immediate fireworks or anything (similar to Emily in her essay), but because the guy I met was just such a gentleman! Not in super traditional ways (even though he held open doors and paid for everything except our end of date coffees), but in the way he took time to plan our date – it gave me the sense that he was genuinely looking forward to it. It helped ease my jitters to meet an authentic and nice person that I left the date wanting to learn more about. It feels nice to face something really intimidating and unknowingly find something warm and friendly on the other side. I’m already looking forward to our next date tomorrow night!

  50. Anneliese Olivia says...

    I enjoyed this piece a lot, Emily. I am married, but I always imagine how terrifying it would be to get back into the dating pool. With all of the apps and texting these days, I’d feel terribly anachronistic.

    Good luck to you in meeting your future best friend!

    • Sasha says...

      The whole idea makes me feel really old too. I would need a young person to tell me exactly how to do this lol.

  51. Clara says...

    I really enjoyed reading this. Thank you!
    I played the “I won’t start dating until..”-Game for a while too. Here is to the serendipitous things that get us back out there, to Cup of Jo, to friends that help you set up and use dating apps and encourage us when it feels like it’s just a “this many creepy antifeminist dudes live very close to you”-app and here is to mothers and their pep talks <3
    Good luck to you

  52. this reminds me of what a friend said, when he started dating after breaking up with a long-term girlfriend. “i’m not ready to have a new relationship, and i tell women that, but i’m just trying to work out my meeting-new-people muscle.” it’s definitely a muscle worth working out!

  53. Ashley Sawyer says...

    Bravo, babe! Dating is hard! I left my partner of eight years when I was 28 years old, and it took me quite a while, now 32, to earn my confidence. Throughout the process I’ve reminded myself over and over again that there’s no scorecard, and there’s no manual. Do what feels right to you – that’s what we’re all just doing anyway. Giving myself the permission to figure out dating on my own terms, while working on myself as an individual, made all the difference in discovering the joy in it. xx

  54. jaclyn says...

    I don’t know how to say this- I think the topic of online dating has been covered quite a bit. I do think that writers at Cup of Jo have a unique perspective, but I don’t feel like this essay covers much new ground. I want to know what she’s feeling about getting back into dating! What kind of person is she looking for now, six years later? How is her approach to dating different then when she was last single? Does she feel pressure to get back in there, when I assume people around her are settling down? Has she learned anything during this hiatus? Does she feel like she missed out or was it worth it? Gimme more!

  55. Sil says...

    I haven’t dated in six years, as well. This has given me some courage to start again.

  56. Agnes says...

    Love this!! I was single in a huge city for 14 years, dating on and off but no one ‘just right’. I recently moved countries, back to my small home town, and my sister set me up with an acquaintance of hers – 3 months dating and going strong!! Looking back and comparing our histories, we can both see that we wouldn’t have been ready to meet before now, and the timing and fit is perfect for both of us. As we’re older (44 and 46), things are moving fast and I couldn’t be happier! I’ve never met anyone as great and perfect for me as him.. it’s never too late! Good luck to you! :)

    • Sil says...

      Great story!

  57. Bindi says...

    My first thought- This lovely young and beautiful lady is insecure?? ( Yes, Emily, I stalked your instagram immediately.)

    Gosh, there is no telling how many of us are sitting around wondering about our face, our zit, our body that needs to loose 10 (30??) pounds.

    When in reality, we are intelligent and lovely.

    • Ashley Sawyer says...

      So true, we always see ourselves so differently than the world sees us.

    • Joanna Goddard says...

      yes, i agree! i’ve met emily and she is smart, funny and lovely.

  58. Logan G says...

    Love this post! Gosh, it’s been….5 years since I’ve dated. I keep thinking that I’m ready to get back in the game, and then I hold myself back with excuses like “I’m too busy.” (Although I am in grad school full time & working full time.) But I KNOW the honest truth is I’m too scared to put myself out there again. Maybe it’s time??

  59. Heather says...

    this. is. me.

    I *mostly* have not dated for 4 years since leaving my ex boyfriend. There is too much else in life to focus on! I love being single so much, and I so prioritize time with myself, my friends, and family, and time for doing the things that I enjoy, that I can hardly imagine making time for a stranger. But I think I am getting there…

    Thanks for sharing that the date itself wasn’t so bad! Because that’s what makes me nervous, even as an outgoing person.

  60. Claire says...

    Thank you so much for this. I have just come out of a 6 year relationship and have my own list of ‘I’m not dating until…’, which is masking a lot of insecurities. Thanks for the gentle reminder that I will probably never reach them all and they’re beside the point anyway. If I could learn to have some self-confidence as I am now, I could be happier quicker.

  61. Jenny says...

    I haven’t dated for seven years…because I spent my twenties being married. Now I’m going to medical school and Mr. Jenny doesn’t want to come with me. This gives me hope that somewhere down the line, after crying into my pho for what feels like it will be years, maybe dating won’t be such a big deal after all.
    My favorite part of this essay was hearing a little about your strong friendships, the people who swipe left on your behalf and share soup with you and not only know your donut preferences but will seek men out for you on the basis of what kind of donuts they look like they might enjoy. These six years nourished those relationships that will last you forever.

    • Joy says...

      Congratulations on getting into medical school, Jenny, and good luck!!

    • Joanna Goddard says...

      congratulations, jenny! you clearly have an amazing future ahead of you, full of both love and intellectual satisfaction. rooting for you, big time!!

    • Marie says...

      I also had a simultaneous end of a long term relationship and start of medical school. I think overall school has helped my mind look forward, even through the tears, because it is so exciting and busy!

  62. Love this! Just remember, they’re just as nervous as you – I encountered traffic on the way to my first date w/ my boyfriend. He claimed he was running late as well. In reality, he was sitting at the restaurant bar drinking a beer to kill off any nerves – he had arrived 20 minutes early.

    • Joanna Goddard says...

      that’s so cute :)

  63. Amanda D. says...

    What a fun story. I feel like it’s the beginning of a book I want to keep reading. Best of luck!

  64. Cait says...

    I thought I was the ONLY person who repeatedly microwaves coffee gone cold!

    Emily, you are my spirit animal!

  65. Anne says...

    I LOVE this! :) I was the same, no dating for 7 years, straight through college, grad school, and my first real job, until a friend finally convinced me to sign up for online dating. It was the least pressure way to meet someone I could have imagined, and I was also still struggling with insecurities about unworthiness. But lo and behold, four people/two months into the experience, I met my husband! Sometimes I regret being closed off to everyone for so long, struggling with my insecurity and anxiety, but just try to remember – if things hadn’t unfolded the way they did, I wouldn’t have met my best friend, and so I really can’t imagine it any other way.

  66. Lis says...

    Great story!! :) Any chance to find out if you indeed met again? ;)

  67. Cathy says...

    Really appreciated this essay – I felt like I was reading my own dating life story! Its been 9 years since I had a boyfriend (and, ehm, like 9 months since Ive slept with anyone), and I know I have to venture out into the online dating scene. Thanks for giving me a bit more courage…

  68. hunter says...

    This!!!! Thank you for sharing :)

  69. Kat says...

    I LOVE cake donuts. My husband also doesn’t get the preference. Maybe it’s midwestern?

    • Lauren E. says...

      Cake donuts FTW! I had to explain the difference to my husband, who didn’t know there was one. Poor soul. Lost before he met me.

    • MEL says...

      Lifelong Midwesterner, and cake donuts are AMAZING. I’ll eat a yeast donut, but cake is vastly superior!

    • Joanna Goddard says...

      cake donuts! #midwestisbest

    • As a southerner married to a midwesterner this thread solidifies what I’ve long suspected…midwesterners are nuts ;)

    • Sarah says...

      Cake donuts are vastly superior! The texture, the density!

    • Cait says...

      Cake donuts every time!!!

  70. Valerie says...

    Love your honesty!!! Same here, about 8 years… and not the vourage yet to online date. Keep going.

  71. Hannah says...

    Cup of Jo, I love you but you needed a copy editor on this one!

    • Joanna Goddard says...

      oh, do you see errors or typos? sorry about that — please share? xoxo

    • Hannah says...

      The biggest one has already been fixed! When I first loaded, it said “six whole had passed” instead of “six whole years.” This story was sweet, but the overload of commas and dashes – which I also use a lot :) – occasionally made it hard to follow.

    • amanda june says...

      “It’s extremely easy to get a date as woman on a dating app. ” A woman.

  72. Jami-Lin says...

    Emily, I love your voice in this piece! A pleasure to read.

    • Joy says...

      I agree!

  73. Sarah King says...

    I love your writing, Emily! You made me laugh out loud five different times. Good luck with this guy and all your future suiters!

  74. Wow, this is brave of you. As a fellow non-dater, I’d be quite terrified in your place. But it sounds like you handled it admirably. :)