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Becoming Whole
Relationships and sexuality are areas of life that can be beautiful or confusing, life-giving, or painful. Becoming Whole is a conversational podcast for men, women, and families seeking to draw nearer to Jesus as they navigate topics like sexual integrity, relational healing, spiritual health, and so much more.
Becoming Whole
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.
Free Resources to help you on your journey to Becoming Whole
👉Men's Overcoming Lust & Temptation Devotional
👉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)
Well, everyone, welcome to our podcast, part two of our podcast on singleness. If you guys heard part one, you heard Josh and I talk about how marriage can be viewed as 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. But today we want to take a shift and we want to talk about let's talk about singleness in real life. 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 Connelly Gillum. She spent 20 years in DC before returning back home to Charlottesville.
Speaker 1:First of all, connelly 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 going to jump right in. So in the 19-some years that you and I have known one another, 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 Heistand and Jay Thomas. They have a book called Sex Dating and Relationships A Fresh Approach. 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 2:Yeah, you know, it's so funny when I just hear that 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 so when that ended kind of dramatically and I wasn't all I should have been in the ending of that, in fairness, but there was something inside of me I had to grapple with that said, this is the consummate tragedy. Here you are at the end of conceivable baby-bearing years, you've just stopped this relationship and this is actually. You've cast yourself permanently into sort of a tragic position in life.
Speaker 2: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 swim in, that many maybe not everybody, but that many people swim in. And I think I've been the surprised person. Now, oh, 18 or 19 years since then, I've been the surprised person that that was untrue, that it hasn't been tragedy, but I am the surprised person in that journey.
Speaker 1:That's awesome.
Speaker 2:So what would you say surprised you the most? To be warm, full, alive, fruitful, connected, interdependent was only going to be able to come through marriage and nuclear family, and not that marriage and nuclear family, of course, are actually meant to be a means to a lot of that. But I was surprised that it could come outside of marriage and nuclear family. I think that there could be satisfying relational richness. I think has maybe been the biggest surprise to me.
Speaker 1:the biggest surprise to me. Oh, that's good. So, as you think about that, if you think about yourself single sexual person, 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. And so what was it like if you compare what it was like as a younger person to where you are in life now?
Speaker 2:Yeah, well, I would say I pretty much 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 sexuality was the secret door. Like sexual expression, like full-bodied sexual expression was the secret door to life with a capital L. And I think that what that did was it took me down further down roads than retrospectively I wish I'd gone sexually, 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 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. I want to live into it on your terms. I don't see how to do that outside of marriage and sex.
Speaker 2:So there was a constant dialogue with God and I think there was selfishness in some of my and I'm talking hardcore sexual expression, but just some of my sexual ways with men. I think there was selfishness. I think there was selfishness. It wasn't sexualized for me, but there was a selfishness that could show up in a propensity towards dependency with women, and I think that it didn't have an overt sexual component, but I still think there was something that was an orientation towards taking Well, my team latter teen years, 20s and 30s, really up through this breakup. When I was about 41, I guess it was, or 41 or 42, was wrestling, I think, wrestling and kind of suspecting that God was holding out on me. I mean, intellectually I knew better, theologically, biblically I knew better, but experientially 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. Wow.
Speaker 1:Yeah, does that make sense to steward your sexuality? Because, as much you know, we can go with the hey, don't do it, right, right. And we can even, you know, you even say and that includes like porn and masturbation, right, don't do it. But there's such a, there's a much bigger picture than just don't do it in terms of stewarding your sexuality. So what was that journey like for you?
Speaker 2: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. And you know, 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 sexuality being tied up with this design God put into us for full self-giving and like complete self-giving and abandon. 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.
Speaker 2: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 and what did it mean to give it, but on his terms and his ways, and the it not just being my body, but what was it going to be? To give my personhood and to trust. 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 it's very hard to steward one's sexuality if, secretly, you believe God's holding out and whatever goodness is going to come to you, you got to go get.
Speaker 2:So, yeah, I mean I think I'm talking kind of vaguely because it's been messy along the way, but I do think there was a shift and I think honestly, kyle, I mean I think part of it was, think part of it was after that breakup um, I really realized, like my sexuality isn't, 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. No-transcript, and with a little fear and trembling, like I hope you turn out to be good God, because I'm mostly convinced. I'm theoretically totally convinced, but I'm mostly emotionally convinced. But I'm going to take the leap and start praying and seeking to operate that way.
Speaker 1:That's so, so good and I appreciate your honesty about hey, like, I know that in my head, but sometimes my heart has a hard time connecting to that 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. 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.
Speaker 2:yeah, I mean, I, I, 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 there's still a feeling of being cut out, and I do think it's because sex does have this it occupies this idolatrous center in our culture and so it has a power in our psyches. That is maybe, or it occupies a place in our psyches. That is maybe, or it, like, occupies a place in our psyches that has an undue power, but it does have that. So how are we going to deal with?
Speaker 1:it 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 had this sense of man? 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.
Speaker 2:Yeah Well, the first story that pops to my mind is back, and you'll remember this. It's when my two-year-old nephew drowned and he was in the pediatric ICU. So he was not, he was still living, but he was in a coma and he was in pediatric ICU for about eight days. And I remember recognizing 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 the little boy and his older siblings, or the parents of the cousins weren't. And I remember for the first time thinking like Remember, for the first time, thinking like, kindly, 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 because I'm single? That almost feels like I have to pay a price by giving more because I'm single.
Speaker 2:And 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 taste hopefulness and light. 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, 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 than 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 there's been some Saturday nights where I've actually chosen to say okay, god, I don't know what to do with this Saturday night.
Speaker 2:I don't know what to do with, whether it was loneliness or feeling misfit or, I don't know, unmet longing or whatever it was 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 next creative thought, and inevitably things I don't mean dramatically necessarily, but things seem to emerge like call that other friend. You always say you want to work on your oil painting. 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 1:That's so beautiful and I so appreciate the fact that you use the term creative, 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 and to be able to dive into that and to do that knowing nobody has to see it. 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 you deny the feelings like you just talked about, 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.
Speaker 2:Yeah, I think it's again. This is like a weird discovery, but that the holes in my soul that I can feel along the way whether they're relational, they're sexual, they're communal 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 Charlottesville and finally, I did not buy my own house until I was 55. A lot of other people have had their own space before then.
Speaker 2:I was always in communal living situations in DC because of, well, choosing it on some level, also finances compelling it. But what I've been amazed is that I have actually stumbled into the joys of hospitality and so it's creating a space that welcomes people, creating wine and cheese and table conversation. In other words, there's a whole I don't even know what you call it, but it's creative, like there's something for me to offer creatively that ends up having a 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.
Speaker 1:That's so good. That's so good. So let me ask you this. So you know, typically in church, when there's topics around singles and singleness, it's always the 30 and under crew, typically. And so for those of us who are a little bit beyond that, 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.
Speaker 2: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 he's still alive, he's like 102 now, but he was an 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 pierced me and I didn't want to hear those words. And then he said your mother has suffered with you being single. And then I was like, oh, he's getting my business. And I could feel my adrenaline going up and 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 I hop out of the car as quickly as I can. He's dropping me off after dinner with him and his wife and I go upstairs to where I'm staying there in Vancouver and I just turn on a movie because I somehow want to escape what he's been touching on in my soul and it ends up being that old movie, 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. I just start to sob and I realized his words had cut into me and that in a way I wasn't going to get to any freedom in my singleness until I had grieved with the Lord the parts that really did feel like a genuine loss.
Speaker 2: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 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, I think it's 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 to the wounds and then, as the wounds are tended and I don't mean it's a one and done sort of thing, but over time, as the wounds are tended more deeply, with the Lord and hopefully a few others, trusted others.
Speaker 2: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.
Speaker 2:If marriage, aspirationally at least, can bring an image of Christ in the church, I think my being sustained and even starting to discover joy in my singleness brings a picture of the church as it awaits the consummation right, and that 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. And so it's like there's a certain role I think holy role that my singleness can bring to the world around me in terms of mirroring something about Jesus and the church, just like, obviously, marriage is meant to be able to do. So I've taken some strength from that. 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 how might he be pouring out of my life in ways that only my singleness would allow for? Does that make sense?
Speaker 1:Yes, that is just so good and I'm grateful that you are inviting people to that place of grief. Yeah, because I think there's this idea that you know, okay, you just got to suck it up, you got to suck it up, you got to suck it up. Keep on jumping on the dating apps in between, but suck it up and not really bring that grief to the foot of the cross, because there is a grief that Jesus shares with us in that and he wants it. And I don't think we're invited enough to bring our grief to the Lord. And even practicing lament that is a biblical practice, to lament, because those things actually can push you closer to the Lord, 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, Because he understands he doesn't want you to carry it forever. He wants to have this opportunity to then take it, because he's the burden bearer, and then give you something rich and beautiful in that, absolutely, I mean.
Speaker 2: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. 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. 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 yeah, so true, so true.
Speaker 1:Well, connelly, this has been just a wonderful conversation with you. Are there any final? Are there any final thoughts or a final thought that you want to share with our listeners? As for those who are single and are just in that place of contemplating what their singleness means in the grand scheme of life, yeah, I will say this.
Speaker 2:I think the 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 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 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 whose kids' sporting events you see periodically? Ask the Lord. It says God sets the lonely in families, 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. Who knows what God can create, um, really, from what you can't see at all, from seemingly nothing he can create, and it also might be him weaving you in to the life of a family, perhaps from your church, some other context where the shared blood of Christ is what ties you together. And yeah, that's what I would encourage people to ask for. If it's not yet their story, oh thanks so much for that.
Speaker 1:So, connelly, I would love to have you just pray for those who are listening, just to send them off with a blessing.
Speaker 2:Okay, that would be my delight, my joy. So, father, I thank you for Kyle, I thank you for her story and all her levels of grappling and discovering and tasting tears and tasting joy, and thank you for our friendship. God, thank you for this ministry and, god, I do thank you for the men and women who are listening. God, would you do something among us that is beyond what we can ask or imagine relationally? 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 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.
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