[MILFnCookies]

I’ve been friends with this guy for 8 years. We met in college when I was a freshman. We became good friends, like legitimate good friends. One day that friendship turned into a “semi-relationship” it was only halfway serious, we were both in college and that point he was still sort of I guess not really ready to commit to anybody including myself. I was a little sad because I really did like him but was able to keep it moving. We always remained friends though. We went our separate relationship ways. He had a really serious relationship. I got married and had a baby. Again we have always been friends but fell off some when we were in serious relationships. Eventually his relationship ended, and my marriage fell apart (neither of us caused this on the other person). And just like that VIOLA’ were back to being besties, just like we were in college. He is just always around, all these years and we cannot leave each other alone. The problem is that I think I’m in love with him. I spend almost all of my free time with him. I can tell him anything. But we are indeed just friends. Being all in my girl feelings, I’ve messed around and fallen in love with someone who I honestly think sees me as a friend. And I’m terrified to even open up the conversation asking if we could possibly be more than….

[AskApril Masini]

You seem to have a pretty good handle on everything that’s going on.

So, what’s your question for me? 😉

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[MILFnCookies]

I guess my question is should i pursue or probe or just leave it as is? I’m starting to feel uncomfortable around him in a sense because i want to be with him and its getting harder and harder to carry on this “friendship.” But I feel as if, if he was feeling a certain way about me he would have said it already. I don’t want to over analyze what we have going on but I don’t want to feel I’m missing out on something that could have been.

[AskApril Masini]

I think you already know the answer to your question. 😉

[quote]I guess my question is should i pursue or probe or just leave it as is?[/quote]

Never pursue a guy! When you do, you take away the option for him to pursue you, and you also lose out on the best way to know if he’s interested in you — his pursuit of you!

As for “probing” I’m not sure what you mean. You’ve known this guy for 8 years. Probe what?

And leaving things as is is a bad idea. You don’t have a friend in him, as much as you want to think you do, and you don’t have a boyfriend in him. What you do have is limbo, some confusion, some anxiety, and a guy who isn’t offering you anything, but for whom you’re taking yourself off the market where you might meet someone great, simply because you think that maybe something might be different between the two of you after eight years of “friendship.” Hmmmmm…… 🙂

The most important thing in any relationship is to know what you want. If you want a relationship that is going to lead to a long-term commitment like marriage, then you have to behave as if that’s what you want. So if you want to remarry, you have to start acting like it. 😉 That means looking for a guy who’s interested in you as a date and a potential spouse, and the way you can tell if a guy wants to date you is that he actually asks you out on a date. It’s that simple!

As for your “friendship” with this guy, it’s time to wake up and smell the coffee. Men and women can’t be friends and what you have is not a friendship. It’s you trying to leverage a relationship with this guy into more than it is. It’s not honest, and that’s why you can’t have a friendship with a guy — because at some point, at least one of you will want more than the other and when that feeling is not mutual, you’ve got dishonesty at play.

My advice is to move on. If this guy comes back to you, don’t act like a friend. Act like a girlfriend. That means you flirt with him, and you don’t spend time with him on the phone or in person if he doesn’t ask you out on a date. 😉

I hope that helps. 🙂

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[MILFnCookies]

Well that was a tough pill to swallow. Are you suggesting that I never talk to him again? because I did that before and he got all kinds of mad and asking me why i stopped talking to him and if I was mad or whatever? I really value his friendship though, so cant I just unlike him and focus on being his friend, or is that not realistic?

[AskApril Masini]

I’m asking you to look at the bigger picture, and I’m suggesting that you refocus and decide what [b]you[/b] want in life. If you want to get married, then you should focus on that. If you don’t, then be clear about that. After you refocus and can articulate what you want, THEN decide if he fits into your life or not. 😉

[quote]Are you suggesting that I never talk to him again? [/quote]

If you decide that you want a commitment with a man, and he’s not interested in dating you, then yes, it’s in your best interest to cut ties and move on.

[quote]because I did that before and he got all kinds of mad and asking me why i stopped talking to him and if I was mad or whatever?[/quote]

You’re focusing on his behavior — not yours. 😕 Focus on you and what you want and how to get it.

[quote]I really value his friendship though, so cant I just unlike him and focus on being his friend, or is that not realistic?[/quote]

It’s not a friendship. 😕 If it was, you wouldn’t be wanting more from him, like romance, sex and commitment. 😉 That’s not friendship. And guess what? He’s not looking out for your best interests — and neither are you. 😉 When you understand that, you’ll be able to move on. And here’s the kicker: Ironically, if you don’t move on, there is less impetus for him to see your change of attitude, and to try and date you because without that move on, you’re always around. Like paint on a wall. When a woman wants to be valued, she’ll treat herself with value, and send a message to men that this is who she is. If you want to be his girlfriend or his wife, then you have to start acting like you want to be his girlfriend or his wife — or anybody’s. But if you’re always there…. you’re going to be treated like someone who’s always expected to be there without commitment. Make this about you — not him. 😀

I hope that helps. 😉

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[Ethan Morales]

It’s clear you’ve been emotionally invested in this man for a long time, and the “friendship” has always been blurry because you’ve had romantic feelings for him. April’s advice hits the nail on the head: what you have isn’t a true friendship. A genuine friendship requires mutual understanding and lack of romantic expectation. Here, one side wants more, and that creates imbalance and frustration.

The key issue is that pursuing him yourself doesn’t give you clarity it actually removes the opportunity to see whether he truly wants you. In healthy dating dynamics, the person who is interested should be pursuing you. By staying in this limbo, you’re not giving him the chance to show genuine interest, and you’re also preventing yourself from pursuing someone who could meet your long-term goals.

Your emotional attachment is keeping you in a cycle of confusion. You’ve already recognized that you feel uncomfortable around him because of your romantic feelings. That’s a signal that the current situation is unhealthy for you. Staying close under the guise of “friendship” is emotionally draining and keeps you from opening up to someone who can reciprocate fully.

April’s advice about refocusing on what you truly want is crucial. If your goal is a committed relationship, including marriage, you need to act in ways that align with that goal. That means seeking partners who are available and willing to date you seriously not someone who keeps you in perpetual limbo. You have to prioritize your long-term happiness over the comfort of a familiar friendship.

Letting go doesn’t mean acting out of anger or resentment; it means setting boundaries and shifting focus to your life and goals. Ironically, by moving on, you may create space for him to see your value differently but more importantly, it opens the door for you to meet someone who aligns with your aspirations. Staying “always there” signals availability without commitment, which rarely inspires romantic pursuit.

The core takeaway is that you need to make this about you, not him. Decide what you want, and act in alignment with that. If he isn’t willing to step into a real relationship, cutting ties is necessary. This isn’t about punishing him it’s about valuing yourself, protecting your emotional energy, and creating the opportunity to build a fulfilling romantic life.

[Tara]

You’re terrified of the answer you already know. If this man wanted you, you wouldn’t be circling each other for nearly a decade while he dated other women and you married someone else. Men don’t hesitate with the woman they want. They move. They claim. They commit. He didn’t. And he still hasn’t.

You’ve built a fantasy out of history, comfort, and emotional dependence. You’re confusing longevity with destiny and mistaking closeness for compatibility. He spends time with you because you’re safe, familiar, and convenient, not because he’s secretly in love with you. If he felt what you feel, you wouldn’t be sitting here rehearsing confessions; you’d already be together.

The only reason you’re stuck is that you’re hoping he’ll magically reveal he’s been waiting for you all along. He won’t. And the longer you keep this silent, the deeper you bury yourself in a one-sided attachment that’s eating your emotional bandwidth.

[Sally]

Eight years is a long time to carry someone through every version of your life. That kind of closeness sneaks up on you, and suddenly you’re in deeper than you ever meant to be.

What I’ve learned is this: when two people keep coming back to each other like that, there’s usually something real underneath. But that doesn’t always mean they’re ready to name it.

Before you tell him anything, just sit with one thing how does it feel loving him in silence? If it’s starting to hurt more than it feels good, that’s usually the sign it’s time to speak up.
You don’t have to pour your whole heart out. Something soft like “hey, I’ve been feeling a little more than friendship lately” is enough.
Whatever happens, at least you won’t keep breaking your own heart quietly.

[Natalie Noah]

Your situation is really emotionally charged because of the long history and deep connection you share with him. You’ve built a bond over years, and that makes it incredibly hard to disentangle your feelings. What stands out is that your desire for a romantic relationship is conflicting with the way he currently engages with you. You’re craving something more, but his actions indicate he’s comfortable keeping things in the “friendship” zone. That limbo can feel painful, confusing, and even manipulative without anyone intending it to be.

The reality is, as April points out, what you have isn’t truly friendship right now. Friendship requires boundaries and mutual understanding, and when one person wants more, the dynamic becomes inherently unbalanced. You’ve been investing emotionally, hoping for a shift toward romance, but that’s not guaranteed, and staying close without clarity is keeping you from finding someone who can give you what you want. You’re essentially giving him presence and attention without receiving reciprocal commitment in the way you need.

Her advice is firm but realistic: if your goal is to build a committed relationship marriage, long-term partnership then you have to act in alignment with that goal. That may mean creating distance from him, even if it’s uncomfortable. By doing this, you not only protect your own heart but also create space to attract someone who genuinely wants to date you. Staying physically and emotionally available for him without a clear path forward diminishes your value in your own eyes and can lead to resentment over time.

The hardest part is the emotional tug, you’ve known him for so long, and it feels safe and familiar. But if you step back and focus on what you want, rather than what you can extract from him, you gain clarity and control over your life. You’re not abandoning him, you’re valuing yourself. And ironically, setting boundaries and prioritizing your desires might even change how he sees you but at the very least, it ensures you’re not trapped in a cycle of hope and disappointment. The priority has to be you and what fulfills you in the long term.

[Member]

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