Navigating Friendships with Unwanted Advances | Diary Entry No. 18

Welcome back to Unfiltered Diaries — where we say what most people only think.
Today’s letter isn’t about strangers crossing the line—it’s about someone familiar. Someone trusted. Someone you’ve laughed with, confided in, and maybe even loved… just not in that way.

But what happens when a friendship starts feeling like a pressure cooker of unspoken tension and not-so-subtle advances? When you’ve drawn the line, but he keeps toeing it?
Yeah… it gets complicated. And it hurts.

Let’s unpack this one—because loving someone as a friend shouldn’t come with conditions.

Dear Diary,
“I have a male friend, we’ve been friends for a little over two decades. When we were teens we had a small moment of passion (no sex) and just acted like it never happened. We’ve both been in respective relationships but now we are both single. He makes A LOT of sexual innuendos. I’ve made it clear to him on several occasions—while I do love him and he’s a very handsome man, I’m not attracted to him in the slightest.
He says he understands but continues to make it known how attracted he is to me, increasing the jokes and “the things I would do to you” sayings, and gets upset when I don’t feed into it…. I’m starting to rethink our friendship and it hurts.
I’d like some advice.“
— Lostfriendship

When friendship and flirtation start to tangle, the line between comfort and discomfort can blur real quick.

Let’s be honest here—and this might sting a little—a lot of men aren’t friends with women without at least once entertaining a sexual fantasy. That’s not always because they’re creeps or disrespectful. It’s biology, ego, curiosity. And most of them never act on it. Some hide it out of respect. Others, like your friend… just let it ride out loud, hoping the tide turns.

You’ve told him—multiple times—that you don’t see him that way. That should have been enough. And yet here he is, still making sexual comments, still testing the boundaries, and now even catching an attitude because you’re not entertaining it.

Let’s call that what it is: disrespect.

Because if he truly valued your friendship—if he loved you as a person and not just as a fantasy—he’d honor your no. He’d joke less, not more. He’d guard your comfort, not his ego.

Now, some people will say, “Well maybe she’s leading him on…” But sis, you’ve been clear. And honestly, a lot of women do this thing where we try to protect the friendship instead of the boundary. We try to say “no” without making them mad. We downplay, laugh it off, sidestep it. Because we don’t want to lose the closeness, the history, the years of shared life. Trying to cushion that truth because we care about the person and don’t want to damage the friendship. We start doubting ourselves: Maybe I’m overreacting. Maybe it’s not that deep.

But it is that deep.

You’re not crazy for outgrowing a dynamic that no longer feels safe.
And you’re not cold-hearted for asking for more respect from someone who says they care.

Friendship is built on mutual respect. If he can’t keep his attraction in check and respect your boundaries, then he’s not being a friend. He’s being opportunistic.

So yes, you’re right to rethink this friendship.

Here’s what you can do:

And most importantly: trust your gut. If you feel unsafe, unheard, or disrespected—you are.
Have a serious conversation. Tell him again, with firmness—not flirtation, not softness. Clear words.
Let him know that if he continues, you’ll have to pull back or walk away from the friendship. That’s not cruelty. That’s self-respect.

Friendship should feel safe. Not like emotional warfare. Not like you’re dodging jokes that feel more like jabs.

And if he oversteps that boundary one more time? Draw the line with him. That shows he doesn’t respect you—not just as a woman, but as a friend.

You’re not asking for too much. You’re asking to be seen.

So don’t settle for someone who only looks at you like a fantasy, when you’ve made it clear you’re a friend.

📚 Need more support or clarity? Check out these helpful reads:

✨ If any of this felt familiar, or if you’ve been in a similar friendship—what did you do? What would you say to someone going through this right now? Drop your thoughts in the comments below.

💌 Got Something You Need to Get Off Your Chest?

Welcome to your safe space. Say the hard thing—no names, no judgment, just truth.

→ Send in your anonymous diary entry here:
📓 Unfiltered Diaries – Submit Yours

✨ Looking for something beautiful and healing to hold onto?
Explore JD Luxe Creations – A shop filled with thoughtful, curated gifts made for moments just like this.