When Dating Becomes Pastoral Care: Three Stories from the Trenches

It’s been a little over 6 months since my blog post, Single White Female Pastor, and just over a year since I started this online dating thing.
I wrote that original post because in today’s Christian culture there seems to be an unwritten bias that the married life is more important, valued, and desired than the single life. The response to the blog was so encouraging. Not only did I get proposals from Africa, but a number of female pastors throughout out the US wrote comments of support, camaraderie, and resonance.
I’ve been pretty consistent, having about one date a week. Some weeks more – some less. Even when work got crazy in July, I slowed down a bit, but still managed to get in a couple dates here and there. Needless to say, I have collected some stories… as well as learned a lot.

Single Women Pastors—It’s Okay!

The number of single women pastors out in the world today has skyrocketed. Single women are more consistently accepting the call and claiming the fullness of their identity as pastors. Therefore, the church needs to come to terms with the fact that their female leaders will not only be leading, but they will also be out there dating.
I have learned that when telling my story, giving words to the unspoken, we are actually giving others permission to not feel shame, taboo, or in hiding. This post and the previous are my attempts at helping others step out of the shadows and be who they are in all aspects of their lives… including dating.
[Tweet “Single women are consistently accepting the call & claiming their identity as pastors.”] So let’s talk about it! Here you go… the complicated nature of dating as a pastor in 3 stories from the trenches:

The Man in His PJs Who Asked No Questions

Normally, when you go on a first date, you expect someone to present their best self. You can imagine I was a bit surprised to walk into the bar, where I was meeting this stranger, to find my date wearing a worn t-shirt, sweats, and what seemed to be slippers.
It was too late. He already spotted me and smiled. Now, I have to sit down.
As I leaned on the table I felt my eyes start to roll into the back of my head from boredom. I started to time him. He hadn’t asked me a single question since I sat at the table. 10… 15… 25… 30 minutes go by. I finally had had enough of his boring story about concrete and it was time to say something…
“Excuse me,” I interrupt, “Do you realize that you haven’t asked me a single question since I sat down at the table?”
I think his entire face hit the table in shock. Shock that he hadn’t asked me a question or shock that I called him out on it… I’m not sure. Silence.
“I don’t mean to be rude, but we are on a first date and I would think that you might be somewhat interested in the person sitting across from you.”
S I L E N C E… I waited for a response… just staring at him.
“I – I – I am so sorry,” he finally stammered.
From that moment on it was no longer a date. It was a one-on-one dating seminar. We covered everything. I mean we even covered the difference between open and closed ended questions.
Yes, I did let him buy me dinner. Yes, I did buy one of the most expensive plates on the menu. No, he did not get a goodnight kiss. And no, I did not call him for a second date.
You know what, I earned that dinner. And I am darn sure that his next date was phenomenal.
I believe my parting words to him were something along the lines of, “And if you actually want to make a good impression on someone… you might want to wear jeans instead of your PJ’s.”
[Tweet “If you actually want to make a good impression on someone… wear jeans instead of PJ’s”]

The New Christian that wanted a pastor more than a date

In my dating profile I state that I am a “progressive Christian.” It also says on there the school that I attended for seminary. Sometimes you get that one guy that puts two and two together. He will straight up ask me if I’m a pastor.
I usually am a little bummed because the fact that I’m a pastor is usually my first date bomb. Everyone has a first date bomb they drop… “I’m a single dad.” “I’ve been possessed a couple times.” “I grew pot to pay for college.” You get the idea…
Anyways, this guy was able to put together that not only am I a Jesus follower but I like to help other people follow Jesus. He says “I’m super new to the faith and I would really love to have an educated conversation with another Christian.”
Now, my dating philosophy is that if a person seems interesting meet them. But I wanted to go on a date not have a Christianity tutoring session. So I asked him if he was looking to go on a date or have a theological conversation. He said he just wanted to meet up and get to know each other.
I should have trusted my gut…
Not only did this guy not really care about getting to know me, he didn’t know how to stay on topic. He had so many questions about faith and Christ and being a pastor than I could keep up with.
I would try to ask a question to learning about him, but he would just say something to the effect of, “That’s all well and good… so, what do you think about sin?”
I finally told him to ask his pastor if there was a Christianity 101 class he could take and then I told him I had an early morning and had to get home. (YES, I lied… Jesus will forgive me!)
By the time I got home I was exhausted.

The Man Who Use to Be Gay

Sometimes you actually meet someone in person that you are interested in. I know … Who would ever have thought!?! Since starting online dating I have become a lot more bold in putting myself out there in real life. So when I met a nice waiter at a local restaurant I figured, “The worst thing he could say is no.”
He said, “Sure… cool.”
A few weeks later we actually met up at a sushi place in town. We chatted about the what it’s like to live in a small town. I asked about what he did for a living. He then, in turn, asked me about my job.
As I begun to unravel the strange ball of yarn that is being a pastor, his body language began to tell me he was feeling very uncomfortable. I tried to continue to explain my work but I got so distracted by his reaction I just asked, “So you seem to know a bit about the church? Is everything ok?”
He played it as cool as he could, tried to change the focus back on to me, but as I tried to continue to tell my story, he could no longer keep his story inside.
He began to explain to me that in his youth he was thrown under the bus to his entire congregation by his pastor after he confessed he might have had an attraction towards a man. He then became the “gay one” at church.
His pastor, instead of walking along side him as a young man, violated his trust and outed him to the entire congregation, making him an outsider. He wasn’t actually given a chance to find out if he was gay. It had been decided for him.
He moved forward with his life as the gay man he was told he was. His relationship with his family was severely put through the ringer. Time went on and he lived out his life within the gay community. In his 30’s, after being married to his husband for 5 years, his marriage was disintegrating. And then it happened… he realized. He’s not gay!
Now, this man chooses to love all he encounters well. His current sexual identity is not of our concern, nor is it the point of this piece. He was so kind as he unfolded the details of his life to me. You could feel his resentment towards the church. You could feel his frustration with his former pastor who, out of what I believe is fear, did not meet him where he was in the moment.
Needless to say, the date was no longer a date at this point. All I could do was sit and listen. When he was done I simply apologized for all the pain he went through. I did my best to let him know that he was and is loved no matter what.
I then found out I was the first person of faith he had encountered in over 10 years. No pressure to represent all of Christianity. We talked about how different denominations have gone in many different directions on the issue of homosexuality and how church hasn’t done a good job helping people claim the goodness of their sexuality. We discussed how shame culture seems to win every time over love and harmony.
We did try to move past the moment. I definitely felt a responsibility to make sure he knew that Pastor Cassie accepted him. I think I tried to overcompensate and force something with him to let him know he was accepted. Yet, we both knew there wasn’t going to be a romantic relationship.
But what I realized was he didn’t need my acceptance. He just needed me to listen to his story that one night over sushi. He needed me to be a pastor that night, to meet his story with kindness and compassion, to be the first person of faith he had met in over 10 years. He needed me to just be myself in that moment and not be anyone else… pastor and all.

What I’ve Learned

I have been a lot of dates over this last year. Some great. Some bad. Some just so so. I have learned that being a pastor doesn’t disappear when I date. Being a pastor is a way of being for me. I represent Christ wherever I go and with whomever I date. The pastoral is innate within me.
I can’t get away from my identity, even when I date. If I was able to compartmentalize who I am and found a man to partner with, my entire life would have to fit into boxes. I want to be in a relationship where I can be my full self no matter what.
When I date I need to be all of who I am because I am needed to be all of who I am. Or else guys would keep wearing PJ’s to dates or they would not have had the chance to meet a kind Christian for the first time in 10 years.
To all my single pastor friends out there: Be who you are. Don’t hide your pastoral self. Its needed out in the dating world. It might not be fair but it weeds out those that are not up to the work of partnering with a pastor. When/if you do find that person, you know that you have not only represented yourself well but you continue to step into the call God has for you.

About the Author
Cassie Carroll

Cassie Carroll

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Cassie Carroll graduated from The Seattle School of Theology and Psychology, with a Master's of Divinity. Her desire is to help people see God in the midst of life - especially when it feels as though God is not present. In a surprising turn of events, Cassie has gone back to her roots. She is currently the Ministries Assistant at Westminster Woods. Having grown up at The Woods, Cassie is excited to be back in a place that is so dear to her heart. Working with the Ministries Department, Cassie is helping create opportunities for campers of all ages to come and encounter God in the Redwood Forest. Cassie also started The Listening in Place Project, in August 2016. She is collecting stories from church planters, practitioners, pastors, social entrepreneurs, and theologians throughout the United States that are rethinking the way we “do” church. These stories provide hope to the Church that has lost a sense of what it means to belong to each other.

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