Singleness Part 2: with Connally Gilliam

Singleness often exists in the shadows of our cultural conversation, especially in faith communities where marriage is frequently celebrated as the ultimate destination. But what if your life's unexpected path includes long-term singleness? How do you navigate sexuality, loneliness, and purpose when the "happily ever after" narrative hasn't materialized as planned?

Connelly Gillum, author of "Revelations of a Single Woman: Loving the Life I Didn't Expect," brings refreshing honesty to this conversation as she shares her journey through decades of singleness. After a relationship ended in her early 40s, Connelly faced what she believed might be the "consummate tragedy" of permanent singleness. Yet nearly twenty years later, she's discovered surprising fullness, purpose, and joy—not despite her singleness, but partially because of it.

The conversation doesn't shy away from difficult truths. Connelly candidly discusses how cultural messages about sexuality created a persistent wrestling match with God, leading her to suspect He might be "holding out" on her. The breakthrough came not through denying her sexuality or desires, but through reframing them as opportunities for self-giving rather than self-fulfillment. From supporting family during crisis to discovering the joys of hospitality, Connelly reveals how her singleness has allowed her unique ways to reflect Christ to those around her.

For singles beyond the typical ministry demographic of under-30, Connelly offers particularly valuable wisdom about grief and purpose. She emphasizes that acknowledging the genuine suffering of unsought singleness isn't wallowing—it's essential healing work that eventually leads to freedom. And her closing thoughts about how "God sets the lonely in families" provide hope for building meaningful connections beyond traditional family structures.

Whether you're single, supporting someone who is, or simply interested in a deeper understanding of singleness, this conversation will challenge assumptions and offer a fresh perspective on embracing the life you didn't expect.

Contact us today: If you have a question, comment, or need help, email us at info@regenerationministries.org

Free Resources for you!

👉Women 21-Day Prayer Journal & Devotional - (Women overcoming unwanted sexual Behavior)
👉Compass 21-Day Prayer Journal & Devotional - (Wives who are or have been impacted by partner betrayal)

Transcript

Surprised By Relational Richness

SPEAKER_00 0:22

Well, everyone, welcome to our podcast, part two of our podcasts on singleness. Uh, if you guys heard part one, you heard Josh and I talk about how marriage can be like viewed as like the pinnacle of your Christian faith. And we talked a little bit about some practical things that you could do as a single person who is fully sexual being and walking that out. Um, but today we want to take a shift and we want to talk about, let's talk about singleness in real life. Uh, this is something, you know, we can talk about all of the all of the these concepts and things around singleness, but it's helpful when you can hear from someone's real life experience. And so today I have the privilege of talking to Connolly Gillam. Uh, she spent 20 years in DC before returning back home to Charlottesville. First of all, Connolly is a lover of Jesus, and she serves nationally and internationally with the Navigators. And she is the author of Revelations of a Single Woman, Loving the Life I Didn't Expect, and co-authored the book Yet Undaunted, embraced by the goodness of God in the chaos of life. She is a friend of regeneration, and I can say she's also a friend of mine. So, welcome today to you, Connelly. Thank you, Kyle. I'm glad to be here. So I'm gonna jump right in. So, in the 19 some years that you and I have known one another, um, we've had a lot of conversations around singleness and specifically singleness, sexuality, and being in the church. And so I want to get your thoughts on this quote. This is from Gerald Heistan and Jay Thomas. They have a book called Sex, Dating and Relationships: A Fresh Approach. And they say we need to explode the idea that singleness is always a tragedy. So, what are your thoughts around that?

SPEAKER_01 2:38

Yeah, you know, it's so funny when I just hear that uh quote out of the blue. I'm reminded about when I was about 40 or 41, and there was a man who had a ring in his pocket who wanted to get married, and I wanted to make it work, but the more I was forcing it, the more it was clear that I was forcing it. And um, so when that ended, uh kind of dramatically, and I wasn't all I should have been in the ending of that, in fairness. Um, but there was something inside of me I had to grapple with that said, this is the consummate tragedy. Um, here you are at the end of conceivable baby-bearing years. Um, you've just stopped this relationship, and this is actually you've cast yourself permanently into sort of a tragic position in life. I mean, I'm not saying that that was true, but that was what I had to contend with and grapple with. So I definitely think that is in the waters that many, maybe not everybody, but that many people um swim in. And I think I've been the surprised person now, oh, 18 or 19 years since then. Um, I've been the surprised person that that that was untrue, that it hasn't been tragedy. But I I am I am the surprised person in that journey.

SPEAKER_00 4:09

That's awesome. So, what would you say surprised you the most?

SPEAKER_01 4:15

Well, I think I had this sense that um uh a life that was gonna be warm, full, alive, fruitful, um, connected, interdependent, um, was only gonna be able to come through marriage and nuclear family. And um, not that marriage and nuclear family uh, of course, are actually meant to be um a means to a lot of that, but I was surprised that it could come outside of marriage and nuclear family, that there could be rich, I think that it there could be relational, satisfying relational richness, I think has maybe been the biggest surprise to me.

Sexual Desire, Faith, And Formation

SPEAKER_00 5:06

Wow, that's good. So as you think about that, if you think about yourself single sexual person, um what was it like early in your walk with the Lord? And then what it's like now, as you think about what it meant for you to be this woman who is made in the image of God, and part of that image of God is experiencing sexual desires. Yeah. And so, what was it like if you compare what it was like as a younger person to where you are in life now? Yeah.

SPEAKER_01 5:49

Well, I would say I pretty much um drank a lot of what I would just call a cultural Kool-Aid, you know, from TV shows and movies and songs. And I always had a sense that uh sexuality was the secret door, um, like sexual expression, like full-bodied sexual expression was the secret door to life with a capital L. And I think that um what that did was it took me down uh further down roads than retrospectively, I wish I'd gone sexually. And um, and it also never fully delivered the goods, but it did keep me kind of hooked, I think, in a way that, in a way, I mean, I mean, the good thing is I I was never really shut down. So that's the upside. Like I felt like a sexual being. And I remember one time standing before the mirror and kind of doing a scan of my body and saying, Lord, you made all these parts and pieces, but it all belongs to you. Um, I want, I want to live into it on your terms. I don't see how to do that outside of marriage and sex. Um, so there was a there was a constant dialogue with God. And um I think there was selfishness in some of my uh, and I'm talking hardcore sexual expression, but just some of my sexual ways with men. I think there was uh selfishness. I think there was selfishness. It wasn't sexualized for me, but there was a um a selfishness that could show up in a propensity towards dependency with women. And I think that it doesn't have an overt sexual component, but I still think there was something that was a orientation towards taking. So I would say a lot of my 20s and 30s, well, my teen, latter teen years, 20s and 30s, um, really up through this uh breakup when I was about 41, I guess it was, or 41 or 42, um was wrestling. I think wrestling and and kind of suspecting that God was holding out on me. I mean, intellectually I knew better, theologically, biblically I knew better, but experientially, um the church seemed to declare you would arrive when you got married and had kids, and the culture around me was declaring you arrive when you're having sex, and I wasn't doing either. So that left me in a place of a lot of wrestling through my 20s and 30s and early.

SPEAKER_00 8:31

Wow.

SPEAKER_01 8:31

Yeah.

From Don’t Do It To Stewardship

SPEAKER_00 8:32

Does that make sense? Yes, absolutely. And so I'm sure then there was this period where you had to understand what it meant to steward your sexuality. Um, because as much, you know, we can go with the hey, don't do it thing. Right, right. And we can even, you know, you go and you even say, and that includes like porn of masturbation, right? Um, don't do it. Um, but there's such a there's a much bigger picture than just don't do it in terms of uh stewarding your sexuality. So what was that journey like for you?

SPEAKER_01 9:14

Yeah, I remember reading this book. Oh, I can't remember what it's called. I'm looking to see if I can see it on my shelves real quick. Oh, some Indian who probably have the word desire or something by this guy, Ronald Rollhauser. I don't even know if I'm getting that right. It doesn't matter. But he talks about um sexuality being tied up with this um this design God put us put into us for full self-giving and um like complete self-giving and abandoned. And he goes on to make an argument how Mother Teresa, if you remember her, was like this totally sexual being because she was giving it all. And um, and I think part of my understanding of sexuality was getting it, so to speak. And I think the stewardship became realizing, you know, who had God made me to be as a woman, um, and what did it mean to give it? And um, but on his terms and his uh his ways, and the it not just being um my body, but what was it gonna be to give my personhood and to trust? I mean, and maybe that's where the stewardship began to happen when I began to trust that God would give to me what I needed in the journey. Because I think um it's very hard to steward one's sexuality if secretly you believe God's holding out and whatever goodness is gonna come to you, you gotta go get. Um, so yeah, I mean, I I think I'm I'm talking kind of vaguely because it's been messy along the way. Um, but I do think there was a shift, and I think honestly, Kyle, I mean, I think part of it was after that breakup, um I really realized like my sexuality isn't it doesn't belong to me. Um, like I am the creature and God is the creator. I'm just like my gifts don't belong to me. Um and I think that was the beginning of the switch to say, okay, the whole kit and caboodle is down is yours. And with a little fear and trembling. Like I hope you turn out to be good, God. Because I'm I'm mostly convinced, I'm theoretically totally convinced, but I'm mostly emotionally convinced, but I'm gonna take the leap and start praying and seeking to operate that way.

SPEAKER_00 11:58

That's so, so good. Um, and I I appreciate your honesty about hey, like I know that in my head, but sometimes my heart has a hard time connecting to that. Uh, and I think folks need to hear that. And and not just the single folks, I think the married folks need to hear this too, because there are single people in your sphere of influence who are really walking this out and wrestling this out. And sometimes you can be in those groups and they'll go, oh, well, you know, marriage has a lot of hard stuff going on, and maybe you don't really want this, and you know, kind of thing. And and that's not always helpful, right? Because there's still this perception that they are experiencing something that we are missing out on as people.

SPEAKER_01 12:55

I mean, I I I'm I think because sex is, and maybe you and Josh talked about this, but because sex is God in our culture, it feels like if you're cut out from the actual physical practice of sex, not these abstract things about self-giving, blah blah blah, but the actual physical experience of sex, you're actually cut out from worshiping at the altar of our culture. And no matter what anyone else says about like, well, being at the altar is not all that great, blah, blah, blah. You there's still a feeling of being cut out. And I do think it's because sex does have this, like idol, it occupies this idolatrous center in our culture. And so it has a power in our psyches that um it is maybe or it like occupies a place in our psyches that has an undue, an undue power. Um, but it does have that. So what how are we gonna how are we gonna deal with that?

SPEAKER_00 13:56

Absolutely, absolutely. And so I want to backpedal a little bit. So you talked about like this, you know, all in giving yourself to the Lord. Can you name maybe one sort of practical way that you have done that that has helped you have this sense of, man, like I'm giving my whole self into this. This is a way that I can really stand in the fullness of who I am as an image bearer of God, sexuality and all.

Singleness, Idolatry, And Culture

Offering Longing To God Creatively

SPEAKER_01 14:28

Yeah. Um, well, the first story that pops to my mind is back, um, and you'll remember this, it's when my um two-year-old nephew drowned, and he was in the pediatric ICU. Um, so he was not, he was still living, but he was um uh in a coma. And he was in pediatric ICU for about eight days. And I remember recognizing um among his older siblings and the older cousins that because I was single, I was actually available to give to them in ways that the parents of either, you know, either this little boy, the parents of um the little boy and his older siblings, or the parents of the cousins weren't. Um and I remember for the first time thinking, like, Conley, in your singleness and your availability, will you just go ahead and give in a way that maybe other people aren't actually even freed up to give? Instead of being like, well, why should I give more just you know, just because I'm single, that that almost feels like I have to pay a price, you know, by giving more because I'm single. And I there was something that shifted. I was like, okay, I'm all in with these kids. And we did, for those eight days, we did all kinds of things to try and taste joy and taste God's presence and um taste hopefulness and light. Um, you know, everything from dressing up to go bowling to getting crazy slurpees to running to parks to making up songs, like all kinds of things. Um uh and I was somehow able to say, I want to give it all out of my singleness. And that just became like emblematic of even on a Friday, let's say it's a Friday night, and you're like, or maybe worse a Saturday night, because Friday night you're tired, you can watch Netflix alone, but Saturday night you got nothing to do, right? And you maybe tried, you maybe gave it a good effort, right? And so I think like there's been some Saturday nights where I've I've actually chosen to say, okay, God, like I don't know what to do with this Saturday night. I don't know what to do with whether it was loneliness or feeling misfit or um I don't know, unmet longing or whatever it was, um uh unmet sexual desire, which seems to go along with a Saturday night, right? To take it and say, God, okay, I give this all to you, would you just give me one thought, like one one next creative thought. And inevitably, things I don't mean dramatically necessarily, but things seem to emerge, like call that other friend. Um you always say you want to work on your oil painting, try it. And little, I mean, it sounds so small and little, Kyle, but it's almost like when I take all my unmet longings, unmet desires, real and imagined, and I say, okay, instead of clinging to them and turning inward, I offer them up to the Lord and say, please just give me one thing in return. It's like God does it.

SPEAKER_00 18:11

That's so beautiful. And I so appreciate the fact that you use the term creative, um, because I think like we serve a creative God who has made us creative. And sometimes I think when we think creative, we think, oh, I've got to be this artist or singer, or but there are other ways in which God has given you something specific that is creativity for you. Uh, and to be able to dive into that and to do that, knowing nobody has to see it. You know, it's it doesn't have to be on display for the world, it doesn't have to be perfect, it just has to be this moment where you can experience what God has put into you to do and to be fulfilled in every possible way as a single person. And that doesn't mean uh you deny the feelings like you just talked about. You even all of those feelings that come up, it doesn't mean that you deny them, but it is an opportunity to invite God into a space and to see how He will come to you and respond to you in that moment.

Hospitality And Purpose In Later Life

SPEAKER_01 19:30

Yeah, I mean, I think it's again, this is like a weird discovery, but that the holes, the holes in my soul that I can feel along the way, whether they're relational, they're sexual, they're communal. Um, but the holes in my soul can become portals to the heart of God. And out of that, new life can emerge. I mean, I think one of the coolest things now, since I've been in Charleston, finally, I, you know, I did not buy my own house until I was 55. A lot of other people have had their own space before then. I was always in communal living situations in DC because of, well, choosing it on some level, also finance is compelling it. Um, but what I've been amazed is that I have actually like stumbled into the joys of hospitality. And so it's creating a space that welcomes people, creating uh wine and cheese and table conversation. Um, in other words, there's there's oh, I don't even want to call it, but it's creative. It's create, like there's something for me to offer creatively that ends up having relational communal impact that's happening single, that I somehow thought was just the territory of married people with cool, expansive, multi-generational families or something.

Grief, Lament, And Healing

SPEAKER_00 21:03

That's all good. That's so good. So let me ask you this. So, you know, typically in church, um, when there's topics around singles and singleness, it's always the 30 and under crew, typically. Um, and so for those of us who are a little bit beyond that, what would you say to a person who is a little bit later in life who might be listening and is still kind of feeling in that funk of man, I'm 40, I'm 50, maybe even 60, and here I am, I'm still single.

A Holy Role For Singles

SPEAKER_01 21:44

Yeah. Well, you know, it's funny. I remember when I wrote the book on singleness, the most powerful part of the book was actually not my words in it. It was me quoting Dr. Houston, who was an older, um, he's still alive, he's like 102 now, but he was a um older former professor and president out at Regent College, a seminary in Vancouver, British Columbia, and a graduate theological college, they call it. And he said to me when we were driving the car, and I was in my late 30s, he said, You've suffered much being single. And when he said that, it like pierced me, and I didn't want to hear those words. And um, and then he said, Your mother has suffered with you being single. And then I was like, Oh, he's getting my business. And um, and I could feel my adrenaline going up, and I'm trying I'm getting chatty, right? And I'm trying to sort of redirect, yeah, but I've seen God in all these ways, show up, blah, blah, blah, blah, blah. And um, and I hop out of car as quickly as I can. He's dropping me off after dinner with um him and his wife. And I go upstairs to where I'm staying there in Vancouver, and um, and I just turn on a movie because I somehow want to escape what he's been touching on in my soul. And uh, it ends up being that old movie, um, Mel Gibson, Braveheart. I don't know if you remember, but it's got quite a lot of drama and so much pathos. And I'm watching it and I just start to sob. And um, I realize his words had cut into me, and that in a way, I wasn't gonna get to any freedom in my singleness until I had grieved with the Lord the parts that really did feel like a genuine loss. So I think for the person who's over 30 or over 40 and is contending with unsought singleness, one thing is to realize there is or certainly can be for many people, an element of suffering in it. And um, and to be able to grieve, to name it and to grieve it. And like with any suffering, we don't live in it forever, but if we don't own it along the way, um, I think it's our fair, our shared friend Christina, who said to me one time that wounds buried alive never die, they just come back as zombies. And so we've got to tend the wounds. Um and then as the wounds are tended, and I don't mean it's a one and done sort of thing, but but over time, as the wounds are tended more deeply with the Lord, and hopefully a few others, trusted others, um, I think there becomes this strange opportunity to realize that I too, as a single person, am bringing something of Jesus to the world around me that's distinct, that it needs to see in my singleness. If if marriage, aspirationally at least, can bring an image of Christ in the church. I think my uh uh being sustained and even starting to discover joy in my singleness brings a picture of the church as it awaits uh the consummation, right? And that um it's it can speak, and I have the opportunity to discover how my singleness can be experienced and then speak of Jesus meeting me in the waiting. Um, and so uh so it's like there's a certain um role, I think holy role that my singleness can bring to the world around me in terms of mirroring something about Jesus in the church, just like obviously marriage um is meant to be able to do. So I've taken some some strength from that. Um I don't know. So grieving what needs to be grieved, and then looking for what is the good and holy role that God has called me into in my singleness. And who knows, maybe I get married a year from now, but for now, what has he called me into? And um, how might he be pouring out of my life in ways that only my singleness would allow for? That's that makes sense.

SPEAKER_00 26:11

Yes, that is just so good. And um, I'm grateful that you are inviting people to that place of grief. Um because I think there's this idea that, you know, okay, you just gotta suck it up. You gotta suck it up, um, keep on jumping on the dating apps uh in the in between, um, but suck it up and not really bring that grief to the foot of the cross um because there is a grief that Jesus shares with us in that. Uh and he wants it. And I don't think we're invited enough um to bring our grief to the Lord, and even practicing lament, um, that is a biblical practice to lament, because those things actually can push you closer to the Lord, uh, because he wants to take that. And just as you said, there's something then, there's an exchange that will happen that the Lord wants to give you in exchange for that grief. Um, because he understands he doesn't want you to carry it forever. He wants to have this opportunity to then uh take it because he's the burden bearer, and then give you something rich and beautiful in that.

SPEAKER_01 27:32

Absolutely. I mean, um, I think too, as I was able to name, to articulate, to feel, to find healing in my grief, I also began to realize, wow, this isn't just about me. Like we live in a culture that's lost meaningful side of what it is to be human and therefore what it is to love. And I think a lot of the unsought singleness, and I know there's people who seek singleness, but I'm talking to those who haven't sought it but have found themselves there. The unsought singleness, at least in part, isn't just about me and my stuff, or me and my inability to make a relationship happen, or it's also the byproduct of a culture that's lost its way in terms of what it is to be human and what it is to love. Um and somehow that was freeing to realize this wasn't just my issue, but it's part and parcel of some bigger things going on in our culture. And somehow that was helpful to me.

Set In Families And Final Blessing

SPEAKER_00 28:36

Yes, so true, so true. Well, Conley, this has been just a wonderful conversation with you. Um, is there any are there any final thoughts or a final thought that you want to share with our listeners? Um, as for those who are single uh and are just in that place of contemplating what their singleness means in the grand scheme of life.

SPEAKER_01 29:02

Yeah. I will say this. I think the um single people who have seemed on the whole happiest to me do seem to be woven into some kind of families, some kind of family. And um not necessarily their original blood family, though that can be great if that's available, but that's not available to everybody. And so if if that's not your current experience, there's not, you know, some family who you go over and play games with on a Saturday night, or uh whose kids' sporting events you see periodically, um ask the Lord. Um, it says God sets the lonely in families. And that might mean your own family, and that's great. And pray for that. If that is what you want, like pray for that. Uh who knows what God can create, um, really from what you can't see at all, from seemingly nothing he can create. Um, and it also might be him weaving you in to um the life of a family, perhaps from your church, some other um context where the shared blood of Christ is what ties you together. And um Yeah, that's what I would encourage people to ask for if it's not yet their story.

SPEAKER_00 30:26

Oh, thanks so much for that. Well, Connolly, I would love to have you just pray uh for those who are listening, um, just to send them off with the with a blessing.

SPEAKER_01 30:37

Okay, that would be my uh that would be my delight, my joy. So, Father, um, I thank you for Kyle. I thank you for her story and all her uh levels of grappling and discovering and tasting tears and tasting joy. And um, thank you for our friendship, God. Thank you for this ministry. And God, I do thank you for the uh men and women who are listening. God, would you do something among us that is beyond what we can ask or imagine relationally? Would you give each of us just one next idea, one next step that you would help us to live into the fullness of who we are as men or as women, as sexual beings, Lord, and as image bearers in a relationally confused culture, Lord, but in one where you've created us for um rich interdependence and fruitfulness, God. So give us one idea and give us a deep sense of your presence as we journey. Ask all of these things in Jesus' name by the power of the Holy Spirit. Amen.