Dear Ada:

First, I want to acknowledge a part of my last reply that may have felt off. I speculated about a possible sexual attraction to his sister growing up—and looking back, I realize there was no evidence of that in anything you shared. I truly didn’t intend to introduce discomfort. I let an idea run ahead of the facts, and I’m sorry.

I reread your posts this morning. One line that stood out:

“For the past few years, I’ve grown more and more spiteful of their relationship… over time the emotional intimacy of it is really eating away at me.”-

That hit me—because it shows how long you’ve been carrying this. You’re not reacting to a passing frustration. This has been a long-term emotional strain, and it hasn’t gotten better—it’s gotten heavier. That alone tells me this isn’t something that can be quietly tolerated or rationalized away. It needs resolution.

Another line that carried unexpected weight was:

“I can’t help but get annoyed at my boyfriend’s tone of voice when comforting her.”-

Tone often says more than words—it carries emotional truth, those subtle signals of warmth, tenderness, or protection that we don’t always name out loud. You might be picking up on an intimacy that contradicts what he says: “She’s like a sister to me… you’re the most important person in my life.” But when the tone feels too soft, too intimate, too partner-like—it can be deeply unsettling. And hard to forget.

Another line:

“She’s flirtatious, promiscuous, open with her feelings. I’m quiet, reserved, and selective with my emotional intimacy.”-

This contrast may lie at the heart of his attachment to her (I’ll refer to her as “B”). You, Ada, represent steadiness, reflection, and a deeper emotional connection—someone he can build a future with. B, on the other hand, brings emotional energy, spontaneity, and a sense of lightness. So he’s receiving two very different emotional experiences:

With you: commitment, depth, emotional accountability.

With B: freedom, play, and low-stakes emotional ease.

In his friendship with B, he seems to take the role of protector or emotional anchor—especially when she’s in distress. Because she leans on him more than he leans on her, it may reinforce a sense of control or even superiority. Not maliciously, but it can feel good to be needed without having to be vulnerable in return.

B validates him—makes him feel seen, admired, maybe even emotionally useful—without asking him to change, confront difficult truths, or engage in real emotional compromise. That makes the dynamic low-maintenance, emotionally one-sided, and—most of all—safe.

No discomfort. No negotiations. Just affirmation.

But in your relationship, there’s real depth. You bring emotional clarity, needs, boundaries. Without realizing it, he might be leaning on B for “easy” emotional connection while relying on you for structure and long-term grounding. And that imbalance takes a toll—on you.

Another thing that stood out to me this morning is how strange it is that you’ve never met his best friend. After four years, that may be intentional. If it were truly platonic and healthy, meeting her should feel natural. The fact that it hasn’t happened suggests that something may not hold up in daylight.

It seems to me that he’s prioritizing his own comfort over your emotional safety. That’s where the selfishness lives—not in the friendship itself, but in his unwillingness to confront the effect it’s had on you. From everything you’ve shared, this borders on emotional infidelity—where someone gives significant emotional energy to someone outside the relationship in a way that feels intimate, romantic-adjacent, and boundary-blurring.

Ada, I’d really welcome your thoughts on what I wrote—what resonates, what doesn’t, or what feels like it’s still missing. Your reflections are so thoughtful and honest, and I’d love to hear how this lands with you. Truly. 🤍

With care, Anita

Dear Ada:

I’d like to reply more fully tomorrow morning—it’s Thursday night where I am, and I’ll admit I’m a bit tipsy (thank you, red wine). But for now, I want to respond to what stood out immediately.

Pulling together your words: “She tells him about her sexual experiences with other men, often in explicit detail… he accompanied her to not one but two abortions… he sends her the same cute cat memes he sends you… she’s flirtatious and promiscuous… he admitted there was sexual tension early in the relationship, though he now claims it’s gone… and still, he says she’s like a sister to him…”-

There is something off here. And I want to say clearly: this is not something you should have to endure, justify, or tolerate.

If she truly feels like a sister to him, it raises questions. Growing up, was he sexually attracted to his sister? (not an unheard of concept). He says the sexual tension faded—but emotional intimacy often lingers long after attraction disappears. And when boundaries remain blurry, emotional closeness can be just as disruptive to a committed relationship as physical involvement.

The way he engages with her—comforting her through deeply personal moments, listening to explicit stories, replicating patterns of intimacy—is more than casual friendship. It mirrors emotional behaviors we typically reserve for a partner. And that’s where it becomes unfair to you. You shouldn’t have to compete with someone he calls “like a sister,” especially when her presence leaves you feeling confused, uncertain, and emotionally displaced.

This isn’t just about her. It’s about him. His choices. His responsibility. The emotional trust between you is what matters most—and if he continues investing in a connection that erodes that trust, it becomes less about the friendship and more about how seriously he takes your well-being.

You’ve shown so much emotional clarity. The fact that you’re questioning this speaks volumes: your boundaries are speaking to you, and you’re listening. That matters.

You don’t deserve to be caught in a dynamic that drains you. And if he refuses to hold your experience with care, then maybe—tipsy as I may be—I’ll say this plainly: let him go. Let him invest as deeply as he wants in that connection… without you having to witness it.

I’ll write more tomorrow. But for tonight, know that I hear you. And I’m angry on your behalf because what’s happening isn’t okay.

🤍 Anita

Dear Ty:

Your message carries such clarity, warmth, and depth—it’s hard not to feel moved by the way you’ve put all of this into words. What you’re naming—the disorientation of witnessing someone change and then withdraw, the sorrow that follows anger, the difference between wanting connection and being equipped for it—is tender and true.

You’ve said it so beautifully: “sometimes love shows up to mirror, not to stay.” That kind of insight doesn’t come easily—it’s earned through pain, reflection, and the quiet courage to let things be what they were. And honoring that without bitterness? That’s grace.

Your desire to meet her in the middle, to offer steadiness, was never a weakness. It was generosity. And I think you already know that her leaving doesn’t undo what you brought into that connection.

Letting go of the hope to carry both people’s healing is a powerful step. Hard, but freeing. You didn’t abandon her—you respected the limits of what one heart can hold. And you left room for hers to take responsibility when it’s ready.

Thanks for letting me walk beside you in that reflection.

Warmly, Anita 🤍

Dear Alecsee:

This is a long message, so thanks in advance for reading. I’ve spent some time revisiting our conversations—starting back in March 2019—and wanted to reflect on something I’ve noticed that feels important.

In your post two days ago, you said:

“I think after that I got kind of in a panic mode and I started making rash moves.”-

That moment speaks to something I’ve seen across your stories: a deep fear of being left behind. This panic, this anxiety isn’t just about losing the relationship—it’s about losing emotional safety and self-worth tied to connection.

You also said:

“I always feel like I lose part of myself when I move on… and become a hollow shell of my empty self.”-

That line suggests that relationships have become so tied to your sense of identity, that when they end, it doesn’t just feel like loss—it feels like disappearing, which is common in anxious attachment and unresolved abandonment wounds,

Over the years, you’ve shared moments that reflect this same pattern:

Feeling desperate to keep someone close, even when the relationship feels shaky.

Struggling with overthinking and racing thoughts, especially after an argument or breakup.

Jumping into new connections quickly, hoping to fill that emptiness.

Blaming yourself when someone pulls away—and questioning what you did wrong.

Sometimes this can be linked to what therapists call anxious preoccupied attachment style. It means wanting closeness badly, but fearing rejection or abandonment. You’ve said things like:

“I haven’t been able to focus at work… I really don’t want our story to end.” “Since the breakup I’ve gone really hard to chase women…” “Honestly… it’s not a good and healthy relationship but I still want to be connected with her.”-

That last one especially reminded me of something from childhood—how kids cling to caregivers even when they’re hurtful or distant. Not because the relationship with them is healthy, but because the fear of losing connection feels too heavy to bear. From my experience, even though my relationship with my mother was terrible (she was abusive), I desperately clung to her nonetheless.. because I was too scared to be completely alone.

In your latest posts a couple of hours ago, you wrote:

“Should I wait to tell her my confession after a few days? It was it meant to be there at the last conversation?…Or am I worrying about this too much and should just let it go? Maybe I should have said…”-

That mental back-and-forth is part of what I’ve come to recognize in you. Thoughts spiraling back and forth between what you should’ve said, what you might still say, and how it might be received. That kind of overthinking usually shows up when there’s a lot of emotional pressure underneath and it can make it hard to hear your own needs clearly. And that’s not weakness—it’s just what happens when emotional stress gets too high.

You’ve been carrying a lot. Anxiety, regret, heartbreak, and the hope that someone will choose you completely. But here’s something gentle to think about: maybe this isn’t about saying the perfect thing at the perfect time. Maybe it’s about giving yourself space. Soothing the part of you that feels panicked, uncertain, and scared to lose love again.

This might not be about whether she chooses you. It might be about whether you’re ready to start choosing yourself.

And for that kind of shift, therapy could help. Especially a therapist who understands fear of abandonment, anxious attachment, and how hard it can be to regulate emotions when you’ve been hurt. You deserve a place where you can talk honestly, feel safe, and start healing patterns that have been exhausting you for years.

If you ever feel ready to explore where some of these patterns come from, I wonder what your early relationships looked like—how emotions were handled, how connection felt growing up. No pressure to answer, but sharing those memories can often bring clarity to the present.

You’ve already done so much self-reflection. That’s a powerful step. You don’t need to carry this alone anymore.

With care, Anita

Dear Alecsee: You tried your best to show up and be present, even while feeling unsure. It’s okay to have regrets—those feelings are part of caring deeply. Her quietness doesn’t mean it didn’t matter. Sometimes people shut down when things get heavy. You were there, and that counts. Be kind to yourself.

With care, Anita

Dear Tea:

Thank you for sharing all of that—it was brave and beautifully honest. I really hear the mix of longing and confusion, and I want to start by saying: there’s nothing wrong with you. Not for wanting love. Not for wondering how or where it could happen. Not for questioning whether you’re compatible with men just because your social world leans heavily toward women.

You’re not incompatible with men; you’re just moving through spaces where emotional depth is more commonly found among women. That doesn’t mean it can’t exist elsewhere. It does.

You don’t need to adopt “masculine” interests unless you’re truly curious about them. Trying things like outdoor volunteering, mixed-gender workshops, or travel experiences could open new doors—but only if they feel authentic to you.

It’s not about changing who you are. It’s about placing yourself where connection has room to grow. You already carry everything love requires—depth, courage, and emotional presence.

I’m here if you want to explore next steps together.

Warmly, Anita