28 More of my Worst Dating Moments

Blogs about Heather, love, Millennial in Ministry, Relationships, single in ministry

Right before my 26th birthday, I came out with a list of my most memorable and terrible dating moments. It went “viral,” at least, in my world. I STILL have people bring up this post at parties and gatherings, which usually ends up with people huddled around a phone, laughing at my misery. If you missed that post, stop and read it here.

I have had many more crazy moments, some I didn’t share in the last one and several more that I experienced in the short 6 months between that post and falling in love. One of the things I most enjoyed since my last post is how many women have opened up to me, confessing their own tales of horror.

As I said in my last post, opening up about these moments takes some vulnerability–even though I was intentional and careful about dating, I still found myself dealing with creeps. Unfortunately, we live in a culture where our first thought is “How’d you find yourself in this situation?” and end up blaming the woman. That said–don’t judge, just enjoy:

  1. The guy who, when I asked what his favorite genre of movies is, he responded with, “Well, I really liked Mall Cop 1, but I hated the sequel.”
  2. The guy who broke up with me through text saying, “You’re a Proverbs 31 woman, and I would have loved that in college, but you’re too good for me today.” He didn’t get far enough with me to have known that I resent that passage.
  3. The guy who texted me every day for two months after I broke things off with him, each time saying “you’re pretty and I miss you.” You’re desperate and I’m blocking you.
  4. The guy who messaged me 6 months after breaking up with “How’s your bod?”
  5. The guy who randomly messaged me a year after we dated with “Sometimes you just need to make out with a pastor and get some holy kissin’ in.”
  6. The guy who I met online, and we quickly established that he was another local UMC youth director. Five minutes into chatting he asks me if I want to “come over and snuggle.” Lawd.
  7. The guy who, after several months of flirting online, we finally go on a date. Afterwards he texts me, “are you okay with having sex before marriage?” The guy was the worship pastor at his church.
  8. The guy who ghosted me (I was okay with it, to be honest), but several months later texts me to check in with me because he still thinks I’m a decent person. He said that he ghosted me because he “just can’t have sex with a youth pastor.” As if there was an offer?
  9. The guy who, after a month of dating and after a really great date, immediately texted me: “I think things are going really great with you, and I can see this going somewhere. First you just need to accept my devout atheism.” …how is this the first time this came up? (okay, enough with text tragedies)
  10. The guy who moved here from California a week before our first date. I asked him why he moved and he said that he felt like God told him to, and he didn’t know why yet. After Facebook stalking him, he moved to Indiana because God told him he was going to find a wife. And he told all his family and friends that. In a public Facebook post.
  11. The guy who knew I was cooking dinner for him for the first time, and then showed up three hours late. It was my first time ever cooking for a man. Ever. But I pressed on.
  12. Another guy who, on the first time I cooked him dinner, I asked if he had any allergies. He said none, but apparently he was severely lactose intolerant. He spent 20 minutes in my bathroom after dinner.
  13. The guy who I didn’t realize was ghosting me; I thought he was just wrapped up in finals week in his last semester of grad school. Being the wonderful woman I am, I made him a finals week care package and left it on his front porch. I didn’t hear from him again.
  14. The guy who wouldn’t let me eat any of the nacho cheese from our pretzel app on the first date. I made a joke about how people in Indiana like to dip everything in nacho cheese, so he told me I couldn’t have any. I sat there and choked down a dry pretzel…and tears. I love cheese.
  15. The guy who thought it was appropriate to put his hand in my bra on the first date. Before you judge me–he was too slick. Obviously he had some practice.
  16. The first time I went over to a guy’s house, he had me drive around the neighborhood for thirty minutes because his mom had decided to pop in.
  17. The guy who gifted me a copy of “The Mist” on our third date because I said I liked scary movies.
  18. The guy who texted me all day before our first date, asking me what he should wear and what I would want to order when I got there.
  19. The guy who couldn’t stop staring down my dress on our first date as I was talking.
  20. The guy who, on our first get-to-know-you date, kisses me on the couch of my favorite coffee shop. And when I laugh and pull away, he kisses me again. Don’t ruin coffee for me, dude.
  21. The guy whose apartment had no furniture but a futon and a card table, with mallard wallpaper on the walls of his duplex.
  22. The guy who parks his car in the shed behind his house. You know, with a padlock.
  23. The guy who, on our second date, suggested we carpool downtown because he had a “really great parking spot.” The parking spot was a mile away from where we were going.
  24. The guy who invited me to dinner on our second date, then asked me if I minded paying for my own. Then he says to me, “I”ll get your drink though” and gave me a wink…as if paying for my $4 drink was a favor. 
  25. The guy who gave me two craft beers on our second date because I told him I was into craft beer–in truth, it was a thoughtful gift, but I had a terrible gut-feeling about him. Later in a text message he was very forward with me about progressing the relationship, so I told him that he was moving a little too fast for me and that I didn’t want to have another date. My gut feeling about him was correct: He got angry with me, and demanded that I give him the beers back. As in, threatened me. I told him that he could get the beers from the nearest police station, if he so liked.
  26. The guy who I wasn’t dating, but this is still a dating story: My good friend liked him, and we all went out one night dancing. He put a kiss on me, and I told him that I wasn’t into him. He disappears, and next thing we know we’re all asked to leave. We still don’t know what he did to get all of us kicked out, but the manager was clear that it was his fault. When I reject guys, clearly they go crazy.
  27. The guy who, when we were messaging on the dating app, had an entire conversation using Beyonce lyrics. I was hopeful. But in person…..his personality was terribly dry. Just awful.
  28. The guy who wanted to take me out to a nice breakfast, and we ended up at Perkins. I’m not knocking Perkins, just don’t tell me Cracker Barrel is gourmet.

Apologies to the men who are reading about themselves. Maybe next time, to the next woman, try not to be so lame? ;)

**As an aside–the picture that I picked for the header to this post is from Breakfast at Tiffany’s, and I used to joke that it was my dream come true to kiss a man with a cat between us. How my life has become just that!


You remind me of God.

christianity, church, discipleship, friendship, god, identity, love, Relationships

When is the last time you looked at someone you despise (because, let’s admit it: you don’t like everyoneand was able to pick out characteristics in them that remind you of God?

I was asked this about some people in my life who hurt me, and I really struggled: It’s easy to find things about a person we don’t like, but what about things we like about them?  Better yet, what are some things in them that remind me of God?

Being able to say, “I see God in you” has impacted my relationships with those I struggle with.  I’m now able to say to them: “You are very creative. It reminds me of God.” “You are outgoing. It reminds me of God’s boldness.” “The way you love people reminds me of God.” It has radically impacted relationships…and even if they don’t appreciate the comment, it helps my heart to focus on these things.

Let’s expand here and think outside our “enemies.”  When is the last time you encouraged a friend, telling them you see the Lord in them?  For me, almost never. When a friend told me how I remind her of God, it only confirmed what I was learning: It changes people when they hear how they relate to the Creator of the universe.

So here is your homework for this week: Focus on a few people in your life–at least one friend and one not-so-much–and tell them what you see in them that reminds you of God. What message is more powerful than that?

Two articles that changed the way I think and minister to teens about sex and relationships.

love, Relationships, women, youth ministry


A little over a year ago, I took my purity ring off. Not because I was swearing off the idea of ever getting married… I just didn’t want it on anymore.

For one, I’m tired of the awkward conversations.  I was tired of people asking me questions about it, because what was I supposed to say?

“I’m waiting until marriage to have sex.” Great, a post-graduate virgin that no one wants to have sex with.

“I’m giving my heart to Jesus until he brings me a man.” Great, yet another young woman “waiting” for a man.

“I’m waiting for God to finish working on a man that will be perfect for me.” Yeah, because I obviously have no work to be done.

So here, a year later, I still have it off. Why?

Waiting assumes that one’s coming…and God may be calling me to singleness. And I mean, I have to be okay with that. Additionally, I have to minister to teen girls and show them that I’m okay with that, because God may be calling any one of them as well. To constantly preach the message to young girls that they need to “wait?” And to celebrate in that waiting? What? Have you every seen a teenager like to wait for anything?

I used to love the song by Superchick called “Average Girl.” The chorus goes “No more dating, I’m just waiting. Like Sleeping Beauty, my prince will come for me, he’ll come for me. No more dating, I’m just waiting. ‘Cause God is writing my love story, my love story.” I used to love that song as a teenager, because I would think “God is preparing someone for me. My prince is going to come. It’s going to happen.”

I feel like teaching our young ladies to “wait” is setting them up for disaster. Have you talked to a young woman about relationships lately?  She will tell you how ticked she is, because she has been waiting like she was told to do, yet no one is coming.  And don’t dare tell her that she needs to trust God more, or that she needs to clean some sin from her life. Because although in some cases that may be true, that’s not true for every case. Some women aren’t supposed to wait…we need to teach that as a reality and not as an alternative lifestyle.


I stocked up on True Love Waits material ever since I signed that pink card and put it on the bulletin board at church at age of 13. I requested a personalized purity ring for my 16th birthday. I even made my own students at church sign that card as well.

So when I started working with at-risk teens, many of whom are teen mothers, and began learning about the way the church has handled their “promiscuity,” “debauchery,” and “fornication” (crazy how they know these words and can’t even read past the 5th grade) I began changing my view of how we teach about sex.

Dr. Kara Powell said at SYMC conference in March 2013: “We have made sexual purity the litmus test for Christianity.” We have taught this to our teens: Once you have sex, it’s over. You’re done. When a teenager comes to us and says they have had sex, we put them at arm’s length and pray for their sweet lost soul.

We teach that if a teenager has sex, they are like a piece of gum that has been chewed. Once chewed, it will never be the same again. We tell them that they’ve given away a piece of their self away that they can never retrieve. We tell them that if they have any sexual contact outside of marriage, they are cheating on their future spouse, and that spouse may not want them if the hear of that person’s sin.

We need to change how we talk about sex:  Not treating it as the unforgivable sin. Sure we talk about a “second virginity” and being a “born-again virgin.” But that doesn’t do anything for the morale; because although we say they are redeemed, we say in the exact same Sunday School lesson that they are that chewed-up piece of gum.

Especially since many of our young ladies may become victims of sexual abuse. Pushing this message actually tells them that they aren’t worthy of ever being loved. That they will never be able to have a marriage with good, Godly sex because a piece of them was given away, whether they wanted it to or not. So why pursue Godliness? Why wait for this perfect man when they aren’t worthy of him? Might as well continue a life of “fornication.”

I have a close friend who believes she is damaged goods: She made a mistake and had sex. And she can’t stop. She, too, was a fan of True Love Waits and advocated it. She had the purity ring, she read “Lady in Waiting.” But she can’t stop. She started because she had low self-esteem, but now she believes she has no value at all, because she gave what was meant for her husband to other men.  I have other friends who have left the church because they were told they were whores; they weren’t told to their faces, but they were taught through the way we teach about sex.

Andy Mineo raps in “You Will” : “You’re never too far to be made new. They said you damaged goods? That ain’t true.”

Dang. How much do women need to hear this?

You are not damaged goods.

I don’t even know how to begin fixing the damage we’ve done, but I’m trying to do one thing: Love my teenagers (and my single girl friends) and show them that they are still worthy of love, and that it’s never too late to be pure in God’s eyes. That I won’t treat you any differently because you messed up, because you got pregnant at 14, or because you were a victim of sexual abuse. You’re not just some piece of gum. You are God’s crowning work of creation.