dear sharideth: i kissed dating goodbye

Dear Sharideth,

I’m 23 (coming up on 24) and honestly, really haven’t dated a lot. Like so many other middle/high-schoolers that grew up in the church, I read I Kissed Dating Goodbye and heeded the well-intentioned wisdom from my mom to skip on dating until I was old enough to at least have marriage on the table as a possibility.

In large part, I still agree with that advice — I’m grateful that I missed a lot of teenage dating drama, still have no intention of playing games with anyone’s heart, and would never date someone while knowing that I wasn’t right for them. Even so, now at 23, I feel like the advice that once “guarded my heart” in middle and high school is has made me emotionally paralyzed in the relationship department.

Over the past few months, I have gotten to know a guy at my church and have sincerely enjoyed spending time with him, though admittedly, I’ve been careful to always make sure it’s been in a group setting. He’s really a great guy – smart, funny, knows his theology, easy to talk to… and our friendship has grown effortlessly. As I’ve been able to get to know him better though, it’s abundantly obvious that we’re two very different people in terms of personality (I’m a play-by-the-rules, people-pleaser; he’s a like-me-or-not, risk-taker); the value we place on relationships (I’m super rational, he’s not so much); our communication style (I struggle with boldness, he doesn’t); and even, it seems at times, our faith (I love my church, while he’s admitted to feeling like church generally isn’t that compelling for men).

In some ways, I see how those differences (granted, all but the last one) could still turn out to be positive things, but now that he’s intentionally expressed interest and asked me out, I’m finding myself absolutely petrified that I’ll mess up a great friendship and worse yet, that once I do, I’ll only have myself to blame for not seeing it coming.

I’m honestly at a loss. He isn’t the type of guy I ever pictured myself with, but it feels nothing short of petty/pansy to turn him down just because there are some potentially surface-level areas where we’re different – and to be fair to him, the things that might be more serious concerns (importance of church, etc…), have never been fully explored because we’ve only spent time in groups.

My current thought is to trust my gut feeling that we’re too different, say no and hope that we’ll remain friends, but knowing that my default response has long been conditioned by the I Kissed Dating Goodbye mentality, I don’t want the true motivation for my actions, underneath it all, to really only be the fear of finally allowing myself to having a response other than the solid “no” I stuck to for so many years.

In short, how do I balance exploring a relationship that could have potential without feeling like I’m playing games? Am I just being wimpy if I stick to my long-held M.O. until I’m more confident in my feelings?

Needless to say, I would be so grateful for any insight you have. Since I apparently couldn’t get all that out without writing what seems like a short novel, I’ll end it there 🙂

Thank you so much for reading.

dear Scaredy Pants,

this is going to be short.  go on the date.

frankly, i’m more concerned about your fear than of any differences you have with this guy in particular.  if i had rejected Craig because of our differences, we would have never married.  nineteen years later, it is my favorite “yes” of all time.

i don’t need all the fingers of one hand to count the number of things Craig and i have in common.  we were even different in our perception of church and legalism and all of that.

but that’s okay.  it’s a date, not a commitment.  now that you are old enough to start thinking about a relationship, you need to keep in mind that this is what dating is for.  take the free meal.  decide if you want to have another.

besides, finding someone just like you is bohhh…ring…

you are not toying with anyone’s heart by going out on a date.  but you might be missing out on a surprise and a blessing if you live in fear of what you think could happen.

i’m thinking different could be good for you.  Craig says that me introducing him to alcohol and tobacco products made him a better Christian.  and yes he’s serious.  it’s because i gave him an opportunity to see something besides legalism and condemnation.  i had a drink and a drag of my brother’s cigar and i wasn’t going to hell.  wow.  amazing.  on the flip side, his sense of reason and practicality is my anchor.

different is good.

different is awesome.

go different!

again, take the free meal.  see what happens.

oh so sincerely,


what do you guys think?  any more advice for her?  do you disagree with me?

ever been afraid to go a date and ended up glad you went?


20 comments on “dear sharideth: i kissed dating goodbye

  1. Evan says:

    I was nervous about asking a girl out in college because we were good friends and I didn’t want to mess it up. Fortunately, I did ask her and now she’s my best friend in the whole world. So if you say no, you may really be ruining a good friendship.

    And I agree with Sharideth. He’s supposed to be different than you. That’s what makes marriages good! I’m a logical, often cold hearted thinker and need my wife to bring my heart to life sometimes. She’s a pessimist who repeatedly predicts her own death and our doom, while I am an eternal optimist who thinks life should have real musical numbers.

    We compliment each other well and work as a team. We have to humble ourselves all the time to meet the other’s needs, but this is kind of God’s plan for marriage anyway.

    So go on the date, and remember you don’t have to marry him for doing so.

  2. JennyBean says:

    Oh absolutely! That is how I met my current boyfriend. I’m also very much a “courting-only” kind of girl, but I learned the hard way that courting doesn’t ALWAYS lead to marriage…and THAT’S OKAY. The aim of courtship should be to work towards marriage, and be in the relationship with intentionality and consideration for the other person’s heart…but at the end of the day, you CAN still find out down the line that “oops we were wrong” and God can bring that relationship to an end. It’s not failure; it’s growth. You shouldn’t become one (emotionally) until you take the vow, you are still two people, so you should be able to retain that sense of self and your personal relationship with God whereby if He asks you to walk, you can do so.

    I was nearly engaged when God asked me to walk, and it took me a LONG time to overcome that hurt, so when a good friend introduced me to her brother and he eventually asked me out, I was very against it. Eventually, the only thing that made me say yes was because I wanted to challenge myself to get out of my comfort zone, dip a toe back in semi-romantic waters, and I was 90% sure I didn’t like this guy so I felt he was a safe bet (HA!) to dip my toes without becoming emotionally entangled. OH WAS I WRONG. And I fought my feelings for him for nearly two months, even told him to get lost once, by the time I finally realised that “umm, actually…I really like this guy, and it scares the crap out of me.”

    We are so different, but it’s wonderful because we challenge each other. It is what makes things fun and interesting and AWESOME. We have tough times, but we’re in it to make it work so we trust God through the moments we can’t understand.

    So I say…do it. Get the free meal. Go on the date. And if you change your mind, after the first date or after two or three, it’s actually okay. You’re not committing to marry the guy. You’re only committing to dating him responsibly.

  3. Bekah Hope says:

    Been there. SO been there. I’ve scared a few guys off with my “I-kissed-dating-goodbye-this-is-serious” mentality. But I went on the date. Went on two, actually. And nobody’s heart got broken. I learned more about him, and I learned more about myself and what I would want in a relationship (not him. Turns out he was more interested in my best friend than me).

    I think “I Kissed Dating Goodbye” was great to encourage us to wait until they’re of marriageable age to date. However, I think it’s created a trend in young people who are paralyzed in their dating decisions because they don’t want to “give away their heart” or fail in a relationship. I read somewhere that Joshua Harris had to republish the follow up book, “Boy Meets Girl”, removing several courtship stories because those couples marriages have since ended in divorce. This was touted as the “foolproof” road-to-marriage plan (adopted into many churches theological foundations). But there is no such thing.

    I know I don’t want someone who is perfectly compatible to me. Where’s the fun in that? How would “iron sharpen iron”?

  4. Rachel says:

    I would say that one thing to keep in mind is that you are afraid to ruin your friendship. Chances are that unless it does turn into marriage, that’s likely to happen anyway, whether through a breakup or healthy drifting apart. It’s great that you are friends now, but what happens when one of you starts dating someone else? You will naturally drift apart from one another and lose a good deal of the friendship you have right now anyway. So I would say just take it head-on and see what happens. I’d rather risk a friendship now in favor of discovering something potentially better than to not make a move because I am afraid to lose a friendship and have to live with wondering what might have been if I’d been more courageous. But take it as slow as you need to maintain your clarity. And keep asking if you guys are right for each other if that’s not obvious as you move forward.

  5. Jenn says:

    Been there done that – and you know what – Dating is fun! I say that as someone who really only embraced dating after 26 at the encouragement of my therapist. Sounds scary and it was – I had spent years not dating because I was waiting for that perfect first date with the man God had put as massive neon sign over his head indicating he was the one. Maybe that happens for others but for myself? I learned that dating is necessary part of maturing – I found out things that I thought I wanted I didn’t and things I thought wouldn’t bother me bothered me beyond comprehension. A date is just a date – if it’s great – awesome! If it’s bad you have an awesome story to tell…

  6. JBen says:

    She should totally go on the date. And she should totally not feel like there is any pressure for it to work out, though that may be harder in practice.

    Also, to totally nitpick at what this guy says about himself, you can’t just say that the church is not compelling for men. The reality is, you are just bored or lazy or not willing to put in the work to be a part of a community. That is all.

    Have fun on your date!

  7. susan says:

    of all the comments and discussion that bit about church not being compelling was the bit that stood out – on a couple of levels. Firstly, frankly I think the guy is right – I actually work in ministry and I still avoid going to church if I can…compelling it is not!
    And for him to say this shows a depth of honesty that should be admired. Especially since she is obviously pretty upfront about her passion for it.
    Sounds like a match made in heaven to me….

  8. Abby says:

    The first two paragraphs of this letter describe me except that I recently broke my pattern of dating avoidance and I find that season of not dating actually improved my relationship competence. I grew up with lots of boys, so I learned to develop healthy friendships with them. Also, friends of both genders have long asked me their perplexing relationship questions and I either answer or – more often – ask questions until they figure it out themselves and we both learn something. I have a small, supportive group of close girlfriends and a couple mentors who love and encourage me.

    Now that I am wading into dating as an adult, I am grateful and surprised to realize how well God prepared me for it while I was not looking. I’ve seen how both genders commonly interpret and misinterpret each other’s actions. I know what advice I would give a friend if she were in my situation (often “Relax, it isn’t something to worry about” or “Just tell him that and don’t expect him to read your mind”). Most of all, I am not depending on a date as my sole source of love and encouragement so it will not be tragic if one does not work out.

    • Jess says:

      I really identified with this: “Now that I am wading into dating as an adult, I am grateful and surprised to realize how well God prepared me for it while I was not looking.”

      had a conversation with my boyfriend along those lines recently. He’s dated a lot, and I haven’t, and I’ve been frustrated with myself, feeling that waiting too long to interact with the opposite sex has left me relationally stunted. But it turns out that my unfamiliarity with the rules of the game is one of the things that he really likes about me. It cuts down on the amount of mind games.

  9. Bethany says:

    “I Kissed Dating Goodbye” ruined everyone’s dating life, but this girl has an opportunity to break the curse! Go on the date. Go casually. If you go on a second date, go because you want to see him again–not because you want to see him forever. A date is not a marriage proposal, and you don’t have to act like it is.

  10. Don’t worry about the differences they can become strengths. Look at the Yin Yang it makes a whole. This year will be 30 years with my wife… Yeah I’m old… We are the Yin Yang… My weakness is her strength and her weakness is my strength. We complement each other.

    The “Kiss Dating Goodbye” had “some” good ideas but also caused a lot of problems. Truely Biblical would be arranged marriage but that is another blog!

  11. Steve240 says:

    You might find my blog of interest where I critique Josh Harris’s book:
    “I Kissed Dating Goodbye: Wisdom or Foolishness?”

    I believe his book has both. Unfortunately Josh Harris isn’t that transparent about sharing the problems his approach has caused though he is quick to point out what he sees as the defects of dating.

    Hope this helps.

  12. Totally go on the date. Definitely.
    I was intrigued by the comments that she is super rational while he is not, and that she struggles with boldness while he doesn’t. My man and I are kind of that statement in negative.
    He is the rational one who keeps me grounded and sensible when I spin off on one, and yet I can talk about anything under the sun quite happily and openly while he gets embarrassed really easily. But my bold approach is helping him to relax and open up more and he’ll find himself telling me things that he has never told anyone before, just because he is so relaxed with me.
    I’m genuinely honored that he feels that way around me, and that I’m having such a positive effect on him. It’s a fantastic part of our relationship that we both look forward to exploring more in the future.
    Differences can be awesome. Don’t reject them. Make the most of them. They can be the most fun parts of a relationship.

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