Cascade a decade

Woman I’ve had an on/off romantic connection with for years proposed date two, then told me I could “move on.” Now she hasn’t replied. How would you read this?

I’m a man in my 30s and I’d appreciate some outside perspective because I have too much history with this woman to be completely objective.

I’ve known her for close to a decade. We originally met in slightly unusual circumstances through an app, ended up going on dates, kissed, and there was clearly mutual attraction, but nothing ever developed into a proper relationship.

Over the years we’ve repeatedly come back into each other’s lives. We’ve crossed paths on dating apps again, suggested meeting at different times, and had various almost-dates/plans that never went anywhere.

Importantly, this hasn’t just been me chasing her. Thinking back, she has probably suggested meeting more often than I have. Once she invited me over and offered to cook for me, then cancelled because she was exhausted after travelling. There was also at least one occasion where we started arranging something and I pulled out and never properly rearranged it.

So our pattern has basically been mutual interest followed by bad timing, passivity or something interrupting the momentum.

My own history probably matters too. Most of my previous relationships happened because the woman created a lot of the early momentum. She would message, arrange another date, want to see me regularly, and I would gradually fall into the relationship.

I haven’t often been in the position of deliberately thinking, “I really want to pursue this particular person and now I have to wait and see whether she comes toward me.”

I also became fairly guarded after being badly betrayed in a relationship before I knew this woman. On our recent date she told me that a previous serious boyfriend of hers had also cheated on her. I’m not assuming that explains either of us, but it may be relevant background.

Recently we reconnected again and this time I consciously decided I didn’t want to repeat our old pattern.

We went on a proper date that lasted several hours. The conversation was very personal and wide-ranging: relationships, work, creativity, life direction, family, mortality, etc.

Toward the end I admitted I hadn’t initially been sure whether she considered it an actual date or just two people with history catching up. She made it clear that she had considered it a date.

She then initiated kissing. We kissed for quite a while afterwards and she explicitly complimented my appearance.

There was also a slightly drunken/affectionate moment at the end where something along the lines of “love” almost came out and we both ended up saying something very emotionally affectionate. I am not treating that as a literal declaration of love. We’d been drinking and have years of familiarity. I only mention it because the ending of the date was clearly emotionally charged, not indifferent.

Afterwards we both talked positively about seeing each other again.

At one point she suggested a casual daytime activity together. She also suggested I could meet a close friend who was visiting her, with the alternative being that we could do something ourselves afterwards.

That never happened and we both let contact drift for a couple of weeks.

Normally that would probably have been where our old pattern repeated itself.

Instead, I contacted her again and jokingly referred to our habit of never getting beyond the early stage.

Her response was very enthusiastic and, importantly, she herself proposed a specific day for date two.

So this wasn’t a reluctant agreement to something I was repeatedly pushing for. She actively created the plan.

Her life does seem genuinely chaotic at the moment. She has been dealing with changes around work, a demanding side income/project, an unpredictable schedule and a pet she is extremely attached to.

She was actually late and somewhat rushed on our first date too. She didn’t seem like someone who had spent hours preparing for it, but once she arrived she was completely engaged with me for hours. So I don’t automatically read her disorganisation as a lack of interest.

Shortly before our planned second date I messaged to confirm.

She replied that her pet had suddenly developed a worrying medical problem. She had already made multiple urgent vet visits and there was uncertainty about further treatment and the cost.

I believe that situation was genuine because there had been health issues with the pet previously, long before this date was arranged.

But then her message went beyond simply cancelling.

She apologised for how absent/preoccupied she had been generally and basically told me that she would understand if I decided I didn’t want to wait around for her because I deserved someone who could be more attentive.

At the same time, she also said that she would contact me again.

That was what confused me.

It seemed to contain both:

“I intend to come back.”

and:

“I understand if you leave.”

I waited a couple of days before replying because I wanted to think about it.

I won’t post the actual messages, but I essentially told her that I hoped her pet recovered and that I understood why it needed her attention.

I also explained that my own life is very busy at the moment. I’ve recently taken on a more demanding role, work longer days, commute and study outside work, so I wasn’t expecting constant texting or huge amounts of attention from her anyway.

I told her that when we were physically together, I had found her very present and attentive, and that mattered more to me than frequent messages.

Then I told her that I had deliberately become more forward with her this time because I didn’t want us to repeat our historical pattern where things between us were always left vague and unresolved.

But I also made it clear that I wasn’t approaching this expecting an instant serious relationship. I admitted I don’t even know exactly what I want myself.

My point was basically: I like spending time with you and I want to see what happens if we actually give this enough continuity to find out, rather than deciding beforehand what it has to become.

I then acknowledged that this was getting a bit emotionally heavy for text and said I would leave it there and let her concentrate on what she was dealing with.

I did not ask her to define the relationship, reassure me, arrange another date or immediately tell me how she felt.

She hasn’t replied.

It has now been around a week.

There is also some older context that may or may not matter. Years ago she spoke openly about having had a number of shorter relationships, sometimes being swept up by initial chemistry only for it to burn out, sometimes second-guessing relationships when commitment became more real, and finding emotionally difficult communication hard to handle over text. She also described needing relationship momentum and sometimes taking time to understand her own feelings.

That was years ago, so I’m not using it as a diagnosis or assuming she hasn’t changed. It’s just hard not to notice some possible similarities.

One other thing she doesn’t know: I haven’t really been dating much for several years. I’ve had opportunities to meet new women through apps but generally haven’t felt motivated enough.

Seeing her was different because I specifically wanted to see her.

That doesn’t mean I secretly decided I want to marry her or even necessarily want a conventional relationship. I genuinely don’t know yet.

Recently I’ve actually found myself thinking about very ordinary things rather than just sex or chemistry: seeing her after a stressful day, getting food, spending part of a weekend together, going for a walk, etc.

I think what I really want is enough normal contact to discover whether we actually fit into each other’s lives.

So my questions are:

• Does her “I’ll contact you, but I understand if you move on” message sound more like overwhelm/guilt, genuine uncertainty, or a soft exit?
• Does the fact that she personally proposed date two shortly beforehand change how you interpret it?
• Was my reply reasonable, or did I make an already stressful situation emotionally heavier than it needed to be?
• Can someone genuinely be attracted to and interested in someone while still pulling back when the connection starts becoming more real?
• How much weight would you give the years of repeatedly coming back toward each other compared with the current silence?
• And given that she specifically said she would contact me, would you now leave the next move completely with her?

I’m not looking for reassurance that she’s secretly in love with me, and I’m equally not looking for a one-line “if she wanted to, she would.”

I’m interested in how the whole pattern looks to people who have no emotional investment in either of us.

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