Moving to a new city in my early twenties felt like stepping into a world where no one knew my past. It was freedom in its purest form. I left my small town behind and entered a lifestyle it wasn’t accustomed to—new faces, new rhythms, new rules. I had to build friendships from scratch, learn how to move in unfamiliar spaces, and figure out who I was without the weight of history following me.
Dating in that season was adventurous. It was spontaneous. It was light, reckless at times, and driven more by curiosity than clarity. I was learning myself in real time, and dating reflected that.
Dating again looks very different at 37 than it did in my twenties.
What frustrates me most isn’t being single—it’s how the past tries to reintroduce itself the moment people find out I am. Old connections resurface, men who once had access to a version of me I’ve long outgrown suddenly feel entitled to reappear. As if the single Jennie they knew years ago is the same woman I am today. She isn’t.
Im healing in ways I wasn’t before. I’m intentional. And I no longer entertain lifestyles—or men—that don’t align with where I’m headed.
I’m not dating for sexual attraction. If that were the goal, I could have sex the first night and call it a day. That’s easy. What I’m looking for is something deeper: a fun, safe escape with someone I can trust—someone fair, firm, consistent. Someone I choose to submit to, not because I’m desperate, but because it feels secure and earned.
Do I want to jump into a relationship tomorrow? Absolutely not.
But I also refuse to degrade myself by entertaining someone who doesn’t meet the standard of the man I’m looking for.
I’ve fumbled men in my past too—but I don’t circle back with “hey big head” messages. If they didn’t serve me then, they wouldn’t serve me now. Growth teaches you that nostalgia isn’t the same as alignment.
Dating in a grid you have been in for over 10 years, almost feels impossible to meet someone who doesn’t know someone you know. Everyone knows everyone. There’s always some overlap—someone you dated, someone you kissed on a wild night, someone connected to your past. And it’s disappointing how quickly men reduce you to a version of yourself that only exists when they want it to. They don’t realize that spontaneity doesn’t equal lack of intention.
I know what I want.
I know when I want it.
And I also know how to protect myself.
Free will doesn’t disappear just because you’ve grown. If I wanted to make out with someone tomorrow, I could. But when you’ve been through what I’ve been through—when you’ve survived abuse, heartbreak, and betrayal—you learn discernment. You learn restraint. You learn that not everyone deserves access to you.
I’m a Mom first. When I date, I date one person at a time until it no longer serves a purpose. Right now, I’m not actively looking for anything serious. I’m not even looking at all. I’m simply enjoying myself—on my terms.
If I meet someone I’m attracted to, I’m open to seeing where it leads. But the moment something feels off—one wrong move that threatens my peace, safety, or emotional growth—I’m immediately turned off. No explanations. No overthinking. Just clarity.
Starting to date again after an abusive relationship is hard. It requires courage, boundaries, and patience—with yourself most of all. But I’d rather be selective than available. I’d rather be alone than unsafe. And I’d rather wait than settle for something that doesn’t protect the woman—and mother—I’ve become.
Let’s talk about age gaps—because somehow, this topic still makes people uncomfortable.
I’m 37, it’s not young but it’s not old. Where do we cap off how old we want our man? What’s too young? What’s too old?
I previously dated someone who was 54 when I was 28 & After just one date, I knew I wanted another. Not because of fantasy, not because of status, not because of rebellion—but because it felt right. It felt safe. It felt intentional. It felt mature.
What’s interesting is how quickly people—especially men my age—frame this as a disadvantage for me. As if I’m losing something by choosing someone older. As if age automatically means imbalance, risk, or limitation. Meanwhile, no one questions the emotional immaturity, inconsistency, or lack of clarity that often comes from men closer to my age.
My close friends want to warn me. I understand that instinct—it comes from love and protection. But what they don’t always realize is that risk exists in every relationship, regardless of age. Abuse doesn’t have an age range. Manipulation doesn’t check birth certificates. Neither does emotional safety.
At this stage in life, age matters far less than:
• Emotional regulation
• Consistency
• Accountability
• Intentional leadership
• The ability to communicate clearly and calmly
Maturity goes a long way—and it doesn’t always arrive on schedule.
We live in a time where women are constantly reminded of their age, yet simultaneously told they look “so young.” It’s a strange contradiction. People forget that just because you look youthful doesn’t mean you lack life experience, discernment, or wisdom. I’ve lived. I’ve survived. I’ve healed. I know myself.
And culturally, this isn’t new. Look at relationships like Karrueche and Deion Sanders—yes, he’s nearly old enough to be her father, yet the conversation shifts when the connection appears grounded, respectful, and mutually beneficial. Suddenly, people pause. Because maturity, presence, and protection are undeniable.
Being open to dating older men doesn’t mean I’m regressing. It doesn’t mean I’m being taken advantage of. It means I’m choosing what feels aligned with who I am now—not who I was expected to be.
At 37, I’m not dating for optics. I’m not dating for approval. I’m dating with discernment. And if something feels right—emotionally, spiritually, mentally—I allow myself to explore it without shame.
Age can be a factor, sure. But it’s not the deciding one.
Character is.
Consistency is.
Emotional safety is.
And in this season of my life, I trust myself enough to know the difference.
If you’re a single woman in your late 30s navigating dating—especially after heartbreak, motherhood, or an abusive relationship—what does dating look like for you right now?
Are you dating with clear boundaries, or are you still learning how to enforce them without guilt?
Are you open, but cautious? Hopeful, but no longer naive?
Do you find yourself dating slower, asking better questions, and paying attention to patterns instead of potential?
Maybe dating for you looks like:
• Saying no sooner, without overexplaining
• Dating one person at a time, or choosing not to date at all
• Protecting your peace more than chasing connection
• Being honest about what you want—even if it narrows the field
• Enjoying companionship without rushing commitment
Or maybe this season isn’t about dating at all. Maybe it’s about healing, rediscovering joy, rebuilding confidence, and learning to trust yourself again before inviting someone else in.
Wherever you are, there’s no timeline to follow and no rulebook to obey. Dating in your late 30s isn’t about proving you’re still desirable—it’s about honoring how much discernment you’ve gained. It’s about choosing yourself first and allowing connection to meet you where you are, not where you used to be.
If this season has taught us anything, it’s that intentional dating isn’t about scarcity—it’s about self-respect.
For the single mothers stepping back into dating—especially after loss, abuse, or long seasons of survival—this is your gentle reminder: you are the prize.
Not because of how you look, how young you appear, or how much you give. But because of who you are. Because of the woman you’ve become through healing. Because of the wisdom you carry. Because of the life you nurture and protect every single day.
Dating doesn’t get to rush you. Age doesn’t diminish you. And choosing peace over chaos doesn’t make you boring—it makes you discerning.
As women, we are taught to prove our worth through availability, flexibility, and sacrifice. But God never designed us to shrink ourselves to be chosen. He designed us to be covered, led, and honored. When you move with intention, when you guard your heart, when you trust your discernment, you invite alignment—not lack.
So whether you’re dating someone older, younger, or choosing to date no one at all, remember this: you don’t need to audition for love. You don’t need to compete. You don’t need to explain your standards.
You are already chosen.
You are already worthy.
And in every season—single, dating, or waiting—you are the prize.
With lots of love, Jennie 🫶🏻
LotsofJennie 