Conversation with My Boyfriend

Hey Uncle Gary,

My boyfriend (31M) and I (24F) were talking about age gaps in dating. For context, we met when I was 22, and he was 29, so we have a gap ourselves. Before him, I’d only ever been in a long-term relationship with someone just a year older than me, so this dynamic is very different.

During the conversation, he told me that at 31, he would still be “willing” to date someone as young as 18. His reasoning bothered me. He said women his age have “too much baggage”, too many breakups, too many past relationships, don’t listen, don’t trust men, harder to get pregnant, and so on. Basically, he sees younger women as easier, less complicated, and more “fertile.”

Then he used me as an example: that he liked my age because I only had one boyfriend before him, didn’t think “all guys are the same,” listened to him, and “looked up” to him. Yes, he tells me I’m pretty and have a lot going for me, but he also made it clear that my age and lack of experience were big factors for him. That already didn’t sit right with me.

This is also the same man who thinks a single woman who travels is a red flag. So when he says dating younger is “better” and “less stressful,” it honestly sounds like he wants someone young, impressionable, and easy to shape. That’s what really unsettled me.

I told him I thought the whole mindset was hypocritical. He criticizes women his age for having the exact kinds of experiences he has had. Meanwhile, we’ve been dealing with jealousy and insecurity issues; he gets upset if I have normal conversations with men, brings it up later, and says he needs reassurance every time. But somehow that isn’t “baggage,” yet women his age supposedly have too much of it.

On top of that, he went into this whole thing about fertility, how younger women are more likely to get pregnant. I have PCOS, so conceiving may be challenging for me, but even then: being young doesn’t guarantee pregnancy, so the logic feels shallow.

There’s more. When we first met, I was 22 and about to transfer to a university. I had two options: a fully online bachelor’s program or attending classes in person. I work full-time and was weighing what would allow me to succeed. When I shared this with him, instead of supporting my goals, he immediately pushed me toward the online program because he “didn’t want me influenced by college parties” (I don’t party at all) and didn’t want me around other men. He said I needed to prioritize “what’s best for the relationship” and consider what he wanted before deciding. I ended up choosing the online option because I didn’t want the conflict, but looking back, it feels manipulative.

All of this together has left me really uncomfortable. I wanted to post this to see what people think about age gaps like ours and the mindset he has. Because to me, something feels fundamentally off, and he insists there’s nothing wrong with how he sees it. It’s getting to the point where I’m questioning the entire dynamic.

Signed, Grossed Out

Dear Grossed Out,

What you’re describing isn’t simply a difference in preferences or a harmless opinion about age gaps. It’s a clear look into how he views relationships, control, and the kind of partner he believes he should have. And the pattern here is important.

There’s a reason his comments made you uneasy: they reveal a worldview built on insecurity, not maturity.

A 31-year-old man saying he would date an 18-year-old because younger women are “easier,” have “less baggage,” and can be “shaped” more easily is not expressing a healthy perspective. He’s expressing a desire for a power imbalance, something he can lean on instead of doing the real work of becoming a stronger, more secure partner.

Using your lack of experience as a reason he liked you wasn’t a compliment. It was an admission that he values inexperience because it makes him feel safer and more in control.

Meanwhile, he’s projecting onto women his age the very issues he struggles with himself. He describes others as “bitter,” “hurt,” or “untrusting,” while he’s the one who gets jealous of normal interactions, needs constant reassurance, and makes decisions driven by fear. That’s not just hypocrisy, it’s emotional immaturity.

And pushing you into an online program to avoid imagined temptations? That wasn’t protection. That was control dressed up as concern. You altered your education and professional opportunities to keep him calm, not because it was the best decision for you. That’s a red flag all by itself.

The pieces line up in a straightforward way:

He’s insecure. He’s controlling. And his age-gap philosophy isn’t about compatibility; it’s about maintaining an advantage.

Your discomfort isn’t overreacting. It’s your intuition telling you the dynamic isn’t healthy, and that the mismatch in maturity is far bigger than the difference in years.

You’re questioning the relationship because there’s something to question. And the truth is simple: a partner who needs you to be inexperienced, isolated, or less empowered to feel secure is not a partner who is ready for a real relationship.

You deserve someone who matches your growth, not someone who tries to limit it.

Regards, Uncle Gary