"April Masini answers questions no one else can and tells you the truth that no one else will."

Dating a Younger Man at 39 – Should I Continue or Stop?

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  • #46650
    Nina A
    Member #382,681

    April, I need some dating advice.

    I am 39 years old. After many years, I am dating again. His name is Evan, and he is 31. We met at a small art fair. We talked, laughed, and then went for coffee. One thing led to another, and slowly we started seeing each other.

    He is full of energy and hope. He loves late nights, friends, and surprise trips. He believes life is just starting. My life is calmer. I teach at a high school. I share parenting with my ex and raise two teens. I enjoy quiet mornings and peaceful walks.

    Sometimes I feel like we live in two different worlds.

    Still, he makes me laugh. He listens to me. He respects my past and my divorce. Once I told him I worry I am too settled for him. He smiled and said I am not settled, I am strong. That meant a lot to me.

    But the age gap is always there. People stare when we go out. Someone once joked that I am dating too young. I laughed, but inside it hurt. He talks about moving and trying new things. I think about my kids and work. His life feels wide open. Mine feels carefully built.

    There are also good moments. He cooks dinner at my home. Music plays. My kids laugh nearby. In those moments, everything feels calm and right. This is not fast or wild love. It feels slow and real.

    What should I do, April?
    Should I keep going or stop?
    I’m asking on askapril because I truly need expert advice.

    #46769
    Val Unfiltered💋
    Member #382,692

    babe… that sounds like the kind of love that sneaks up on you when you finally stop chasing chaos 😮‍💨 like, yeah, he’s younger but you? you’ve done the crash-and-rebuild, and now you’re meeting him from a place of choice, not need. age gaps only feel loud when the connection’s quiet.

    don’t overthink the audience. people love to comment on what they don’t have 🙄. if he makes your world feel wider keep going. let it breathe, let it grow, it doesn’t have to look “right” to be right. 💋

    #46879
    Serena Vale
    Member #382,699

    Hey love, okay, first of all, let me just say: I felt every word of that. You wrote that like someone who’s been through enough life to know what real connection feels like, the kind that doesn’t sweep you off your feet, but steadies you instead.

    Here’s the thing, it doesn’t sound like you’re confused about whether there’s something real here. You already know there is. What you’re really asking is whether it’s wise to keep walking toward it, even though it doesn’t fit the story the world says you “should” be living.

    So let’s break this down gently.

    Evan sounds like light, spontaneous, hopeful, wide open to possibility. You sound like warmth, steady, self-aware, grounded in a life you’ve built from the ground up. That’s not a mismatch; that’s complementary energy if both people respect the other’s rhythm. The difference in years matters less than the difference in maturity, communication, and pace, and from what you’ve described, he meets you there. He listens. He honors your story. He’s not running from your reality, he’s cooking dinner in your kitchen, laughing with your kids. That’s showing up.

    Now, about the noise, the looks, the comments, the tiny voice that wonders if people see something wrong here. That’s about them, not you. People get uncomfortable when they see love that doesn’t follow their template. But you’re not living for their comfort. You’re living for what feels true when it’s quiet and no one’s watching, and you’ve already described that feeling: a quiet kind of rightness. That’s not something to throw away easily.

    The question I’d ask you is this:
    Does this relationship add peace to your life more often than it adds confusion?
    Because peace, not perfection, not fireworks, is the real test of love that’s meant to last.

    If the answer is yes, then keep going, one honest step at a time. Let it unfold without overthinking where it “should” go or how long it “should” last. Love doesn’t have to look like your past, or anyone else’s future, to be worth living.

    And if someday the age gap or lifestyle difference starts to truly pull you apart instead of drawing you closer, you’ll know. You’ve already proven you know when to walk away. But don’t cut something off now just because it challenges the shape you thought love was supposed to take.

    You’re not robbing the cradle. You’re reclaiming joy.
    And that’s nothing to apologize for.

    #48628
    AskApril Masini
    Keymaster

    A 38 years old woman with a 31 years old man isn’t robbing the cradle. Whoever said that is dumb.

    Put all the noise aside and focus on just you. Whether you should stay or go depends on your answers to these questions.

    Are you happy in this relationship?

    Is he as committed to this relationship as you are?

    Do you both want the same thing out of this relationship?

    If he never changed a single thing about his lifestyle, his pace, or his priorities, could you live with that?

    Do you trust him with your kids?

    If you answered yes to all of those questions, then there’s absolutely no reason for you to leave. Block out the damn noise! 😂

    But if your answer is “No” to any of those questions, you already know what you need to do.

    #50203
    Lune David
    Member #382,710

    Honestly, reading this felt close to home. I’m a guy, and even I’ve been in situations where someone comes into your life right before Christmas and suddenly everything feels different — good, but confusing in that grown-up way. Your story doesn’t sound wrong at all. It sounds real.

    The age difference only feels loud when the connection is quiet, and what you described with Evan doesn’t sound quiet. It sounds like someone showing up, especially in those small moments that matter more during the holidays.

    And trust me, every year around Christmas and New Year’s Eve, I end up needing to AskApril because that’s when all the emotions start kicking in harder than usual.

    If this guy gives you peace, presence, and room to breathe, don’t let outside noise ruin something that’s working. Sometimes the best “holiday gift” we give ourselves is letting something good grow at its own pace.

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