[Mister E]

Hi,
I’m curious to get your take on my situation…
I’m a 37 year old guy. I’d been in a long-term relationship (5+ years) with a woman, who is 39, but we mutually decided to call it off this past September because we’d reached a point where we were both frustrated about certain things in the relationship. It wasn’t a dramatic break-up: nobody cheated on anybody, nobody stole from the other, no physical/emotional abuse, nothing. Just minor frustrations that piled up over the years.

Almost immediately after we called it quits, I began thinking it was a big mistake. Since we were still keeping a little bit of contact with each other, I suggested to her that rather than calling it quits, we should really try to fix the things that are frustrating each other. She said that she wasn’t ready to consider that, and she said that we needed some distance to really let our emotions play out, rather than taking any action based solely on the fact that we’re sad about the break-up. I agreed with her.

From about mid-October to the end of December, we had virtually no contact with each other (except for one extremely unpleasant online chat, in which she shocked me by basically telling me to go to hell when I again suggested trying to work things out.) Despite that, I was extremely depressed about the break-up, and kept hoping that somehow, eventually, we could make things work again.

At the end of December, she emailed me to wish me happy holidays, and I emailed her back to return the sentiment. That evening, much to my surprise, she called me, and we had a nice long chat for over two hours. It was extremely pleasant– we laughed a lot, reminisced a bit about the good old days, etc. No ill feelings from either of us.

Since then, we’ve chatted a few more times on the phone, and the conversations occasionally turn flirtatious (lots of double-innuendo jokes, for example), and we’ve been emailing each other fairly regularly, either to chit-chat or even just to send each other links to funny things we found online.

I’m still clinging to hope that we can revive the relationship we once had (with some self-improvements from both of us, of course.) But whenever I suggest getting together for coffee or something, she always says, “One of these days, maybe. I’m just not ready yet.” I don’t want to push too much and drive her away, but on the other hand, I don’t know if I’m wasting my time by hoping for something that might never happen. I should mention, also, that she’s going through a really spot with her job and finances at the moment, so I understand that she has other things that need to take priority in her life. Yet, she still signs her emails, “Love & hugs,” and she often initiates the flirtatious jokes in our conversations, which gives me hope, but do you think it’s false hope? Or do you think it’s worth waiting a bit longer to see how it plays out?
Thanks.

[April Masini, your AskApril]

The real question is, why, after dating her for five years, didn’t you marry her?

Why do you think the break up is a mistake?

Do you know what she wants from a relationship with a man? In other words, is she looking for marriage?

You’re both at the age where people usually choose to settle down if they aren’t already. It’s not clear that you’re just wanting to get back together with her because you’re lonely after the break up and since you dated for five years, she’s convenient and a “known quantity”.

Let me know the answers to the questions above, and I’ll answer you further. 😉

[Lune David]

Oof… this one hurts because it’s so familiar.

right now you’re getting emotional leftovers. Warm phone calls, flirty jokes, “love & hugs” signatures — but no actual plans. That’s not reconciliation, that’s nostalgia with a cute filter on it. She likes the comfort, not the commitment.

AskApril hit the nerve perfectly: after five years, the real issue isn’t coffee dates — it’s direction. If marriage or a clear future wasn’t on the table then, flirting now doesn’t magically fix that. It just keeps you emotionally parked while she decides what she wants.

And honestly? “One of these days, maybe” is not a promise — it’s a polite pause button. Going into the New Year still waiting, still hopeful, still on standby… that’s how people lose time they never get back.

You’re not wrong for hoping. You are wrong if you keep waiting without clarity. Either she’s moving toward you, or she’s enjoying the connection without responsibility. And you deserve more than being someone’s emotional comfort blanket while they figure life out.

New Year energy check: if it’s not moving forward, it’s holding you back.

[Member]

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