Taking The Plunge

A couple of years ago {it’s hard to believe I have been blogging long enough that I can refer to a post that I wrote a couple of years ago}, I wrote a post asking readers their thoughts on online dating. I loved hearing peoples’ opinions. They were fascinating. They were informative. But most of all they were encouraging.

And so a few months later, I decided to try to have an open mind and put myself ‘out there.’ But as quickly as I dipped my toe in the online dating pool, I decided that I wasn’t ready. I had great reasons. My life was full. My heart was otherwise engaged. And it felt truly UNCOMFORTABLE.

Online dating was something I hoped, prayed, and pleaded that I would never have to revisit. But here I am, 35-and-single and living in a town where I can count the single guys that I know on my right hand AND where I have a friend {Bianca Juarez Olthoff} who isn’t ready to let me give up on my heart’s desires. {Truth be told the second factor weighs much more heavily than the first.}

So, with some {okay, with A LOT of} poking and prodding, I have taken the plunge and now officially have a profile on one of those wacky internet dating sites. {Note: I can’t really say that I created an online profile, Bianca did most of the heavy lifting while I entertained myself with snarky commentary and an ice cold beer.}

I am trying to keep an open mind about the whole thing but right now I still am struggling with the general uncomfortable-ness of reviewing awkward pictures and clumsily edited profiles of potential suitors. So I find myself reluctantly browsing but fervently praying that I’ll stumble upon my ‘dream dude’ in some old-fashioned ‘normal’ way. {Maybe like the way I met one of my college boyfriends? With him dousing a Naty Light on me at a frat party. True story folks. True story. Not my best day but yet it provides stellar blog fodder.}

Here is where you provide any advice, commentary, testimonials, or funny stories in regard to online dating. Do share. I’m all ears. 


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Lindsey has a sincere love for her precious dogs Molly and Maisy, a good red wine and the Delta Sky Club.

Please note: I reserve the right to delete comments that are offensive or off-topic.

  • Kathy G

    I totally understand.  I was a single girl in my early 30’s who decided to take the online plunge.  I figured that I’d get a couple free dinners and some good stories out of the experience.  I was happy with life, all be it a little lonely, but wasn’t expecting anything to amazing to happen.  God’s plans were much different.  He brought a wonderful man into my life and in April we’ll be celebrating our 5th wedding anniversary.
    Be open!  Have fun!  And if nothing else, you’ll get some great stories!

    • Anonymous

      Super cool Kathy!

  • Amy

    It was how my friend met her happily ever after!

  • Christy

    Good Luck!  Have fun and stay open..I have met some GREAT friends and had some wonderful relationships from online dating!  It can be alot of fun and you will get some additional blog fodder as well! 🙂

    • Anonymous

      You’ve never met a stranger though! 🙂

  • Anonymous

    I’m single, and in my 20s.  I started online dating a little less than a year ago, and since then I’ve had several first dates.  Three developed into ongoing dating relationships, but none developed into a steady, exclusive dating relationship.  If something doesn’t work out, then that’s OK!  Don’t feel like every relationship has to be “the one” that works.  Even if it doesn’t ultimately work out, like Christy said, you can make some good friends in the process.

  • In our last life group – out of the 9 couples, 4 had met online.  Big things ahead and maybe even through this internet thing Mr. Dream Dude. 

    And if things don’t work out, you tried and you’ll have lots to post about 🙂

    • Anonymous

      4 of 9…That’s nuts. 

  • I am sitting here laughing because my friend and I were just talking about this last night and while chatting on gmail we made profiles to an online dating site.  At 33 and living in a very small town… it’s time to try something different!
    I completely agree it is so uncomfortable…and way out of my comfort zone but I am going to give it a try.  Still decided between 3 and 6 months.  

    Best of luck to you Lindsey!  🙂

    • Anonymous

      You too Christy!

  • Okay, my story: 37 and divorced from a few years (I have bipolar disorder, and it destroyed my marriage).  I held so MUCH against myself until last April when I cried out to God and told Him that He had to know that I have tried, that I couldn’t bear this burden anymore.  It was the first time in my life that I understood what it meant to “forgive myself”.   And to this day I *still* don’t know why but, I signed up on eHarmony.  Even though I was TOTALLY content with whatever God wanted me to be, including single.  I’d sooo found peace and joy with the simple presence of God’s grace!

    A few weeks later I began communicating with this one girl on eHarmony who said that like me, she was also a fan of “Weird Al” Yankovic.

    Long story short: God has led me to my soulmate at last.  We’re already talking about getting married later this year or early next.  She is absolutely everything that I have needed to fill that absence in my life, that I did not know was there.

    Just leave it to God, good lady!!  You are sowing the seeds.  Now let Him bring the increase 🙂

    • Anonymous

      Very cool story Chris.

  • What if God’s new favorite tool is the internet? {Although it might have to compete with Tim Tebow 🙂 } But seriously, try to keep an open mind. I have recently found the woman I feel like I will marry, and while we didn’t meet on-line, we were unable to see each other for about 9 months and so we got to know each other on-line. When God’s time was right, of course it always is, we were able to become a couple in real life, and it made the experience much better. I think people tend to open up a bit more on-line, so for us, we got some of the basic get to know you stuff out of the way with a little less embarrassment.  No matter what happens, God does have great plans for you!

    • Anonymous

      Thanks Chris!

  • Yay! I’m not sure what was scarier for me: joining an online dating site, or admitting it on my blog. I’ve tried a couple different sites (match and eharmony) and have had mostly positive results. I’ve been on some fun and interesting dates, but still haven’t met the right one. Like you, I think I am hoping I will meet him some normal way…but I’m still putting myself out there online too. Good luck!!

    • Anonymous

      Yeah, it took me a day of sitting of the post before I could hit “publish.”

  • Suebee700

    Hey Lindsey! Hope you are doing well …
    The joys of online dating …. I have taken the plunge several times. I have tried both the free ones and paid ones. I have tried Christian sites and the non-Christian sites. I have answered questions, taken personality tests….

    I have had some “interesting ” people contact me… And I had the awkward first ( and last) meetings. And still I find myself single. It’s still an awkward process.

    I’ll be praying for your journey/experience…

    Susie a.

    • Anonymous

      Thanks Susie! Hope you are well.

  • Though much older than you I found my husband online while living in England. We have been married for six years and we are happily living on a small sheep farm in Latvia. With God in the picture there is just no telling where the path will lead. Blessings and have fun.

    • Anonymous

      Happily living on a sheep farm in Latvia…that sounds wonderful 🙂

  • You’ll hear a lot of advice to “be open!”, and that’s not bad.  Being open to new things, open to what God is doing, open to being surprised, open to things working out differently than you thought they would – all good things to be open to!  

    But sometimes the mantra “be open!” can cause you to doubt your instincts, like when you have that distinct feeling that a certain fellow isn’t for you, yet you feel this pressure to “be open!”  And then things drag on longer than needed.So I’ve had to navigate the balance between Being-Open and Trusting-My-Gut.

    Anyways, good luck with this new venture!  I’m sure it will be an interesting experience.  I hope it will also be a fun experience!  And I double-hope it will be a rewarding one.

    • Anonymous

      Really good advice. Thanks.

  • if he doesn’t show his teeth in pictures of him smiling – he might not have any! (learned that one the hard way).
    email a lot.  a lot.  don’t waste your time with someone who can’t carry on a conversation with you via electronic communication.  my husband and i met on myspace (obviously many moons ago b/c no one uses it any more!)  we talked for 6 months via messaging before we ever met in person.

    • Anonymous

      seriously, no teeth? 

      • sad, little rotted nubs.  i spent the entire evening praying “please don’t try to kiss me.”  

  • Lindsey! I really should comment on your blog more often! I feel compelled to now as I was just having a conversation with a friend yesterday about online dating. I feel like I only hear extreme experiences: “I loved it! It was how I met my husband” or “It was terrible. Just a few bad dates and then I signed off.” I’ve decided–though I haven’t tried it myself–that a successful experience requires exactly what you’ve described: an open mind and willingness to give it a go. I think it takes work and you have to dedicate a chunk of time to it, but I also think online dating is moving with society in the direction it’s going rather than trying to work against it. Good for you!

    So excited for you as you embark on the adventure! Keep us posted!

    • Anonymous

      Thanks Andrea!

  • Bianca

    Love it!!!

  • Oh man… I feel your hesitation, your questions, concerns… I did it for a while and really it wasn’t for me. I have friends who have met amazing people online and so I totally support it, but it didn’t work for me. I actually decided to do something different (http://www.twentysevendates.com/). Not trying to put a plug or anything, but just thought I would share with you my journey. Please continue to share about yours! It’s hard, fun, exciting, tiring… all at the same stinkin’ time! 🙂

    Here’s to dating, getting to know new guys and wearing our heart on our sleeve.

    • Anonymous

      I’ll look forward to following your journey!

  • Cass Comerford

    It’s an adventure – I go into each day so curious about who this person is on the other side that it’s almost always a good time even though it hasn’t lead to finding my someone. Cheers to fun adventures!

  • KC

    I’m in the same boat as you and praying the same thing. After seeing the profiles of who is out there I feel like giving up. But you will get some really interesting stories, trust me.

  • Amanda


  • I have been reading your blog for about a year, I think, and really enjoy your perspective.  Not sure I’ve ever commented.  I’m in nearly the same boat, 31 and and single, resisted the online thing for a long time but recently fell to peer pressure (and the knowledge that I know almost 0 single men), and have been filled with anxiety ever since.  I find that I receive more insulting comments than refreshing ones, and am starting to think I’m actually not ready.  I told a really good story about a ridiculous email I got recently on my (sad and poorly updated) blog, maybe worth your read, but too long to type here.  Good luck!  I’d love to hear more about this journey if you’re willing to share.

    • Anonymous

      Thanks Becki! Let us know if you try it. 

  • I’m in the same boat and am planning to take the plunge this year as well.

    Based on your previous two posts on this topic, something that has worked well for more
    than one person that I know might also work for you. My cousin’s friend, let’s call her Sally, could easy “make a match work in her head,” even when the person wasn’t a good fit. To take the pressure off of Sally from being the sole judge of her matches, my cousin read through the profiles Sally got matched with and then talked with her about them. My cousin said that there was only one out of every 30 or so matches that she thought would make sense for her friend. Sally has been dating a great guy since June and my cousin predicts that they will be married within the year. It sounds like Bianca could be that friend for you.

    Last, did you happen to read on Boundless the article, “Ten Online Dating ‘Don’ts’ for Men and Women” (http://bit.ly/zbkGiM), that Lisa Anderson recently wrote on this topic?  It’s worth reading.

    • Anonymous

      Thanks. I’ll check it out. 

  • Bridget

    Yeah yeah yeah! Have fun and treat it as an interesting new hobby. Some bad dates, some good dates, and lots of great stories regardless.
    I took the plunge online 2.5 years ago. 6-ish guys later I had lots of good stories. But then #7 (2 years ago) came along and he wasn’t just a good story, he was MY good story. 1.5 years later we got married, and today we’re expecting a little bambino in June. If I hadn’t taken the plunge, hadn’t looked at some embarassing profile photos, hadn’t had some awkward first dates and hadn’t given it the full 3 month college try, none of this would have happened.
    Praying for fun adventures for you!

    • Anonymous

      Thanks Bridget! Excited about the bambino! So fun!

  • Just yesterday I started premarital counseling for a couple who met through an online dating site. They both commented how nervous and skeptical they were when they signed up, and they both also agreed that they would never had met otherwise.

  • I’ve had some interesting experiences with online dating – the most memorable one was when the guy showed up and he had no front teeth!  That scared me off online dating for a while, but now I just make sure to screen my dates a bit better!

    • Anonymous

      You are the second person to comment with a no teether. Not good! 

  • Aurora

    I won’t bore you with the details of my story but you can read about it here if you’re interested — 

    I had your exact feelings, maybe even worse when it came to online dating…the Lord used the experience to show me that sometimes He will answer prayers not only in ways we didn’t expect but in ways we didn’t want Him to answer…I feel you on this, Lindsey.  A marriage testimony that included online dating was the LAST thing I wanted!  But give it a try with an open mind. God may just honor your willingness to try something that seems so ridiculous to you. And He still might do it without the Internet!  Praying for you and desires of your heart!

    • Anonymous

      Thanks for the encouragement and sharing your story. 

  • Erin

    go for it! when all you have to lose is maybe an hour of time you won’t get back… no reason not to.

  • Iesha (_chynadoll_)

    “I am trying to keep an open mind about the whole thing but right now I still am struggling with the general uncomfortable-ness of reviewing awkward pictures and clumsily edited profiles of potential suitors. So I find myself reluctantly browsing but fervently praying that I’ll stumble upon my ‘dream dude’ in some old-fashioned ‘normal’ way.”

    Wow Lindsey.  It’s like you’re living in my head.  You are me and Bianca is my best friend. She’s been trying to get me to sign up for one of the online dating sites even though I keep telling her I’m not comfortable with the idea and I’m really not interested in it. Although I am slightly interested but like you, I’m having an internal struggle with letting go of my dream of the way I thought God would bring my mate.  The old fashioned. 

    I’m not knocking the people who meet someone wonderful online.  A lady at my former church met her husband online and she just had their first child.  She was in her early 40s and decided  to give online dating a try before she got any older.  And from all accounts she seems very happy.  So it can happen. 

    I don’t know.  I feel cheated. Like I couldn’t find a guy the “regular” way so I had to have an  aid. I know it sounds irrational but that’s the mental battle I’m fighting with online dating.

  • I think the most important parts of online dating are 1) be honest about who you are, what you look like, what you like, and what you’re looking for; if you stay true to this, you will have a better experience. This draws on the good side of online dating: if done honestly by both parties, you have a filter that helps weed out bad matches. 2) don’t date by email, chat, or phone exclusively. I know all too well the thrill of an email in the Inbox, or a “wink,” or a surprise chat with a decent guy (why are they so hard to find??!) Use online dating as a mere introduction. Take the dating … and much of the get-to-know-you conversation … into the real world. 3) If you’re looking for a guy who’ll be a leader, let him lead. If this is a big deal to you, like it was to me, don’t give into the allure of sending a long message to that guy that seems your type.  I’m not saying don’t indicate a friendly interest, but if it’s really important to you, then don’t impede that leadership from the get go. 4) Pray. A lot. 5) Be careful. Don’t be a stalker, but don’t be afraid to Google your date. Get real (full) names. If it gets serious, consider letting a friend or family member run a criminal background check.

    I found your blog through the Tennessean for some reason (blog list), and I know I don’t know you, but this post made me want to jump in and encourage you! I, too, felt like online dating was being cheated of the real-world meet-in-person and feel a spark kind or relationship. But I still kinda got that … because I followed the “rules” I listed above. One day I was minding my own business, browsing the site I had joined, when I got a chat request from some guy who actually used an actually unique and friendly-but-not-creepy-or-pushy opening. I was intrigued enough to respond to his request. It was election day 2008. We discussed politics, religion, and even the recent death of a loved one of mine. First conversation ever, mind you! We figured if we, total strangers, could handle that conversation full of things you aren’t supposed to talk about around the dinner table, that we should probably get to know each other better. Three weeks later, he asked me on a date. And the rest, as they say, is history. He’s sitting right next to me on the couch we bought together, in the home we rent together, working on a project for the business we own together, and living our life together as husband and wife. 🙂

    Don’t get me wrong: it wasn’t all easy. There is a HUGE learning curve from chatting to talking in person. I had to learn to love his looks and mannerisms and humor and voice after I had already been attracted to his mind and thoughts. It’s a little backwards from normal! (That’s why I say start dating in real life ASAP.)

    So don’t get discouraged. 🙂 And if you don’t feel comfortable with online dating after giving it a second try, that’s fine! I hope and pray that God will lead the right guy to you. Oh and I second all the comments about Boundless. GREAT site.