I’ve known my friend since college. He’s never really dated or shown much interest in relationships until recently, after I broke up with my long-term girlfriend and started dating again. Now he talks more about women—but only about the ones who look like Instagram models.
My friend is an awesome guy: funny, smart, thoughtful, a great cook, and he has a good job. But he’s not conventionally attractive. To be blunt, the women he’s interested in usually want guys who fit a certain “look,” and he just doesn’t.
Lately, it’s clear this is hurting his self-esteem. He dismisses women who actually show interest in him as “ugly.” I’ve tried nudging him toward more realistic options, but he doesn’t budge. I feel like, at our age, we should be past this kind of superficiality and actually see people for who they are.
I don’t want to shame or hurt him, but I’m worried watching him chase an impossible ideal is making him miserable. How can I talk to him about this honestly, without sounding cruel or condescending? I want to help him see his real worth and stop holding himself (and women) to unrealistic standards.
Any advice would help.
Alright, brother, you came here because you care about your friend—and that’s a good thing. But you already know what you need to do: you need to have the hard conversation.
Look, most of us have some fantasy version of what our life and relationships should look like. We think if we just land the “perfect” person, all the stuff we don’t like about ourselves will magically go away. Spoiler: it doesn’t. That’s not how real connection or healing works.
Your friend’s not broken because he’s not conventionally attractive. And you’re not a jerk for noticing it. We live in a world obsessed with shiny objects and Instagram illusions, but real relationships are built on respect, honesty, and shared values—not perfect abs or airbrushed selfies.
You don’t have to tell your friend, “You’ll never date an Instagram model.” That’s not the point. You do have to tell him, “Hey, man, I love you enough to be honest. You keep chasing women who are chasing something else entirely. It’s hurting you. You’re blocking real connection because you’re trying to fill a hole with an impossible fantasy.”
Is it uncomfortable? Yep. Will he get defensive? Probably. But real friends have the conversations that matter, not just the ones that are easy. Tell him his worth isn’t measured by who he can get to like his Instagram post, but by who he is when nobody’s watching.
You’re not responsible for his choices, but you are responsible for speaking truth with kindness. Help him see what you already know: he has a ton to offer, but only if he stops chasing a mirage and starts living in reality.
Lead with empathy, be direct, and then stand by him—no matter how the conversation goes. That’s what real friendship looks like.