One Big Thing I Learned from Dating Online


The other day, I spent some time going through my email, unsubscribing from a bunch of lists, dragging messages into folders, and tying up lose ends in an attempt to be less of a flaky human (a new core value for me).

As I was doing so, I stumbled across a blog post that I had written in March and had completely forgotten about in the depths of my inbox.

It spurred a few ideas. Sooooo I’m going to break one of my self-imposed blogging rules to tell you a bit of a story.

In March, I was doing a lot of one particular thing:

Online dating.

Yep. One of those things that no one really wants to admit to but like, a lot of people do. And hey! I’ll say two great things about it:

  1. I met some really nice, interesting guys.
  2. I learned a metric ton about myself…and have learned to love myself in a way that is allowing me to actually BE ME.

So obviously we’re going to focus on that second part.

You see, this post that I uncovered as I went through my email the other day was a letter.  In hindsight, it was a pretty silly letter. Nonetheless, tossing my pride aside for the sake of the lesson…

It was a letter to the hypothetical guy that Googled my name and found my blog.

I actually had the clever idea to put said letter at the URL (don’t click that, because it never got published.)

Anyway, at the time, while I was going on all of these dates with new dudes, there was one thing that I was irrationally self-conscious about:


All I could think about was how a guy might perceive me based on what I share (or don’t share) in this space. I feared that they’d think I’d blog about them (which is a valid fear but I haven’t really yet…this doesn’t count) or that they’d think I was weird for sharing so much with strangers and for having so many “Internet friends” and such.

To be frank, I desperately wanted to keep them from finding this blog OR if I couldn’t do that (which, let’s be real, it’s the internet), I wanted to at least be able to control the conversation about the blog from the get go.

I was so embarrassed and unsure about this aspect of myself and of my personality.

So I sat down and wrote that letter. Afterward, I felt pretty great about it. It was a good letter. Some of my very best pieces of writing are letters.

Immediately after finishing the post, I slapped on some lipstick went on a date.

And wouldn’t you know, as I rode the high that comes from creating something I was proud of (said letter), I had one of my best first dates. I talked about blogging in a passionate way. I told the dude about my love for the Internet and for learning. He didn’t think I was crazy or weird (or if he did, he didn’t let that fact be known). 

It was awesome.

Anyway, shortly after that, I became a whole lot less worried about people (OK, boys) “finding out” about my blog. And hey! For the most part, this blog has been really well-received by the guys that I’ve dated and that have actually gotten to know me.

And even if it wasn’t well-received by them, it doesn’t matter.

Because if there’s one thing that dating has taught me, it’s this:

Be You, Bravely.

You can’t hide the parts of your life that make you shine or that make you feel ridiculously nerdy and intensely YOU. In fact, that’s probably the recipe for disaster in relationships. Whether it’s your obsession with DIY, your unrelenting interesting in history, your weird obsession with a particular book or show… If it lights you up, embrace it. Own it. Be brave and confident about it.

It’s so tempting to edit ourselves into what we think someone else wants us to be. But at the end of the day, pretending is exhausting. And the right people will love you exactly the way you are.

So that’s what I’m here to say to you today:

Be You, Bravely…especially in matters of the heart.


Now! I’m excited to share something with you guys.

I was recently contacted by Tara, a lovely Etsy shop owner that is creating a bunch of goodies that speak to this very type of confidence. Her shop, Chicago’s Own, features one-of-a-kind photography and designs including phone cases, notebooks, prints and other items you won’t find anywhere else.

Tara is offering one of her notebooks and an iPhone case (pictured above) to one of my lovely readers. In addition, I’ve decided to sweeten the deal with a $50 Amazon gift card.

Big changes are coming to this space and I AM EXCITED. One of the major shifts is going to happen in the intimacy of your inbox, however.

Therefore, the best way to enter this giveaway is to join my email list. It may be a few weeks, but eventually, you’ll be getting weekly (ish) love letters from me. I promise they’ll be short and sweet.

You can enter your email below:

Sign Up for Email Love Letters

* indicates required

As I am a huge advocate of only inviting things into your life that make sense for YOU, there are multiple other non-email ways to enter the giveaway by using the Rafflecopter below and showing some love to Chicago’s Own.

a Rafflecopter giveaway

Conversation for the comments section: What’s the one thing that you try to hide from the world, when you’d be better off shouting it from the rooftops?

OR, for funsies: what’s your best dating story (those that end happily or awkwardly are my favorite)? Dish in the comments.

xo – E


  • Vanessa says:

    I sometimes find myself shying away or downplaying the fact that I blog when it comes up in conversation, which is silly. I’ve been actively trying to change that, since I really do think that my little space is something to be proud of!

    • Erika says:

      YEAH IT IS! Confidence is killer when it comes to blogging!

  • Sarah Grace says:

    I try hiding how really lonely I am .

    • Erika says:

      I feel like I have to hide this as well. It’s really tough sometimes, but I think a lot of people are more lonely than they ever let on.

  • Kourtney Thomas says:

    Thing I hide when meeting new people? My fitness flag. I get so geeked out about working out and running and everything, I know it puts people off sometimes, so I usually just don’t mention it or really downplay it. If something gets mentioned, I open up of course, but typically not right away.

    Jeez, that’s stupid, haha.

    • Erika says:


      I mean, your biceps certainly do some of the talking for you, I will say. 😉

  • alison says:

    I went on some fun first dates while doing the online dating thing. My “favorite” awkward date ended like this: after a non-spark filled first date we both walked out of the coffee shop. Our cars must have been in the same direction. He took the left side of the street, I took the right. At one point the sidewalk ended on the left side so he started to cross the street, saw that I was there and turned around and just walked next to the closed sidewalk. It could have been humiliating or a huge blow to the ego, but I had no patience for less than amazing so I laughed it off and went on with me day.

    • Erika says:

      Ah haha! I’ve definitely had a few no-spark dates that ended in awkward, silent walks back to cars. Mortifying! This is really funny.

      Love this: “I had no patience for less than amazing” <– seriously, exactly how I'm looking at it. No spark, no date #2.

  • Not gonna lie, I explored the realm of online dating and loved it! It was just fun to meet people, and go on fun dates. There was definitely a ‘mixed-bag’ of people – some awkward, some interesting, some stage-5 clingers! Ahhh, makes me laugh just thinking about it 🙂

    • Erika says:

      Hahah SO TRUE. So how’d you meet your husband then? Just curious! 😉

      • I was actually my friend’s moral support when she was dating a new guy and he was having a superbowl party with his friends! Haha. Sebastian was there but we both had really, reeeeeeeeally horrible previous relationships and neither of us were interested.
        A couple weeks later we started hanging out, and even though we hated the idea of relationships, we couldn’t stop seeing each other – and even did so secretly for a little while, haha!!! My family dubbed him my “non-boyfriend”.

  • My most awkward dating story is way too long for a blog post comment, but basically I went on a date with a guy who brought his teacup Yorkie named Charlotte and spent the entire date doting on her, asking me questions then interrupting me to talk to his dog or make comments about her to me, and cut the date short because she started hiccuping uncontrollably. No contact after the date until a week later when he texts me and says, “sorry I haven’t been texting. Charlotte died.” I felt bad for him but had no interest in seeing each other, so I said I was sorry and figured it was over…then he sent me another text a week later with (dun dun dun) a picture of a new dog!

    • Erika says:

      BEST STORY EVAA. Giggling at my desk so much.

      That’s absolutely hilarious. I have not had any quite this weird! I like to think my pre-date screening techniques save me from some weirdness, but man, I love a good story!

    • Sammie says:

      Yikes. As a girl who has never owned a dog under 70 pounds, that is an instant turnoff!

    • Woah, that is nuts. And yet, hilarious. M used to bring his dog to places that we’d both be since he’d heard me say I love dogs. He used her shamelessly to get my attention, but if he’d had conversations with the dog during a date, game over.

  • This is an awesome post. It’s so important to own the things you love, which is especially scary when meeting new people.

    • Erika says:

      Thanks so much Lindsey! 🙂

  • Savannah Darr says:

    I hold a lot of myself back when meeting new people. I tend to get a feel for people before I start expressing my honest opinions or letting my “freak flag fly.” My husband thinks it’s a little crazy but I’ve always done it. Once I get used to people, I show my full self.

  • Sammie says:

    Oh man, so true. I just recently realized that I needed to end it with a guy I was sorta/kinda seeing because I realized I was altering myself so he’d think I was awesome! I’m a book worm and a blogger, neither of which he seemed to find at all interesting, which was awkward for me because that’s what I spend 80% of my free time doing. He’d text me on a Friday night, “What you into tonight?”. First of all, is that even English? Second of all, what does that even mean? Anyway, I texted him that I was reading. His response… “lol”. That should have been the end of it for me. But it took a few more dates for me to fully realize that I was actually too cool for him, if you know what I mean. So what if I prefer to spend my evening reading on my back porch as opposed to getting blacked out in a club. That’s just who I am.

    Blog about dating MORE 🙂

    • Seconding you … I’m beginning to think spending a Friday night reading is a better use of my time 🙂

    • Erika says:

      Hahaha best response: NEXT.

      And we shall see… MAYBE I’ll blog about dating more, though I have to say I’ve cooled my jets on it a bit lol we’ll see if anything of interest comes about.

  • most awkward … awhile back I went out on a lunch date with a guy I’d been talking to for about a week on a particular dating site. He seemed normal on there … well, he became loud and obnoxious and pretty much half the café (that I frequent often) could hear him. And he was ADD, kept changing topics every five minutes, and if my view on whatever he was bringing up didn’t mesh, he told me why I was wrong. We went to leave and the manager passed us and asked if I wanted a refill. I told him “no” … manager’s reply, “are you sure you are okay?”
    Needless to say, it became even more awkward the next day when the guy texted to say he wished he was there to cuddle with me during the ice storm that was hitting.
    Umm, no dude, café manager picked up the same vibe I did.
    Needless to say after a few more instances similar to that, I’ve pulled my dating profile for awhile.

    • Erika says:

      Oh my gosh, that sounds horrible. Haha and I totally understand the need for breaks – I’m always off and on about it. Get the app, delete the app, every few weeks. Haha I wish you much better luck in the future! 🙂

  • Ashley says:

    I don’t have any awkward date stories. Once a guy took me to the woods on a date, which in hindsight is super creepy.

    I have learned with dating: you have to be totally up front about yourself, because it just cuts to the chase. Like HERE I AM. Like it? No. PEACE DUDE. I am currently dating this musician that is super cool. Like I’m still intimidated with how cool he is. And sometimes he’s like “we have nothing in common.” And I always say, “do you want me to act exactly like you, like some creep???” (followed by some impression of him).

    He still doesn’t get the blog thing, which is annoying. BUT, he’s had some lady friends of his come up and ask if they could meet me because they liked my blog. Then, he’s like: I get it.

    I have never done online dating, but I would totally try it! My friends who participate in it seem to have a lot of fun (and good stories).

  • I think I would have been weird about dates finding out my blog if I was dating when I started blogging (luckily I’m out of the dating pool!) 🙂 I was not a huge fan of online dating, I had a system down and would only meet for drinks for the first date. Some guys were weird about it too, but I hated going through a whole dinner when I knew it was not a match. With that said I have several friends who met their husbands from online dating.

    • Erika says:

      I’m so with you on the only meeting for drinks thing – that’s my rule as of late as well… even though the date I refer to in this post was an exception to that rule. Overall, I’m a drinks-only for first date kinda gal as well. I can usually tell in the first 20 minutes if there’s a spark or not.

  • Tiffany says:

    I have been reading this blog for a little while now and I really loved this post! I have tried online dating a few times, but had my most awkward date a couple of months ago. After messaging with a guy who I seemed to have some connection with for a little while, we met up for a lunch date. Turns out he was rude: told the server our chips from chips and salsa were stale although I thought they were fine. He also paid for the date, but then asked me if I had money for the tip. This made me feel awful because of course in the world of debit and credit cards I didn’t have any cash. Although we had a decent conversation throughout the date, I wasn’t feeling any real spark or romantic connection. He sealed the certainty of not having a date two when he awkwardly forced a kiss on me as we were saying goodbye.. eek! I am still hopeful that I will find some success with dating in the future, but if not at least it creates some interesting stories to share with others.

    • Erika says:

      Hahah thank you Tiffany! UGH, rude guys are the worst. That’s such a red flag for me too.

      After a really awkward dinner situation (in which I bailed on the second half of the date due to no spark), I instituted a new rule: Drinks only for the first date. Oddly enough, I broke that rule for the date I’m referring to in this post (which turned out to be probably my most successful “relationship” from online dating – we’re friends now), but overall it’s been a good strategy. Usually you know in the first twenty minutes or so!

      Best of luck out there, keep on keepin’ on! 🙂

  • Caitlin says:

    I have so many weird / ridiculous dating stories — many from online dates that I found! One of the best was this guy who was really awkward + inexperienced, but sweet. We played pool + at the end of the night, when it was time for him to leave, he kinda just plopped himself in my car + took up residence. Every time he’d try to kiss me, he’d start shaking + say he thought he was gonna throw up from nerves. So I tried to just call it a night, and he ended up sitting in my car, talking about his nerves, for the next 2 hours!! (Yes, I am way too nice.) At this point it was 3am + I needed to go home, but oh no… what’s that? A knock on my car window? Hello, police! They wanted to know what we were up to, sitting in a running car in a dark parking lot at 3am. I finally told the police that he was too nervous + wouldn’t leave my car, but I was tired + kinda over the date. The police walked the guy back to his car + I never spoke to him again. Clearly, it was a match made in heaven!

    • Erika says:

      That is SO BIZARRE. So bizarre. Oof. You are a much nicer person than I!

  • Regan Vasconcellos says:

    I don’t know exactly what pulled me in. Perhaps it is the “metric ton” of change I am curious about.

  • Tabathia says:

    That everyone who loves to read should read Harry Potter books

  • Elizabeth says:

    I’ve done the online dating thing a couple of times and each time was a different experience as I grew as a person and learned more about myself. I’m an open person to an extent but I try to hide how much I am really feeling sometimes to keep from being too vulnerable. I am learning to communicate better those extra emotions and kinda think my last online dating adventure helped teach me more about that. P.S. I met my boyfriend on my last online dating adventure 🙂

    • Erika says:

      I think you’re so right about vulnerability and learning to communicate – definitely big challenges for dating in general.

      And YAY! I love hearing success stories from it! That’s awesome.

  • AmandaSakovitz says:

    I try to hide how much im lacking in confidence.

  • Love this Erika. I did online dating for about 5 minutes, after an incredibly awful dating experience with a guy I knew through mutual friends. But, it just wasn’t for me. The problem I had with dating was a lot of the guys who would ask me out where guys I met on the job doing a story. If I talked to them outside of work, they’d almost always say “that’s off the record.” Seriously guys. Of course, some of my friends do it too and it drives me nuts. I’m a reporter, but most things people tell me aren’t even newsworthy and if I don’t have a notebook in my hand, I’m just a regular person.

  • […] period of dating and general boy-craziness that left me frazzled and confused. While I may have learned a lot in those months of countless first dates and awkward text messaging, my favorite lesson was that no […]

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