Vacations are the kiss of death for my relationships.

I broke up with Leo three nights ago. I’d been writing about how I felt about him and doing my usual processing of things. I’d spoken to my Mom earlier in the week and decided I’d just see how things played out. There was no “burning platform” to break up. No crazy blog-finding (Fox) or police action (HWSNBN) or wives who found out about a relationship (Tony).

I decided to see how the next few weeks went, now that I’m finally relatively physically mobile and we could have more active dates. It had been 5 weeks without any Tony contact and I was working my way through that.

But the decision wasn’t sitting well in my brain.Then I talked to Hyacinth and she sagely pointed out that I am a super nice dater. I am kind and thoughtful and diplomatic and really think things through before I make a decision (it’s not always a positive). She said “you never make an impulsive decision. You crunch every bit of data you can possibly find and do all sorts of tests, and your decisions come only after hours and hours, even days worth of contemplation.”

You see, I’d said I felt like a bit of an asshole because a) Leo is really a stand-up man, and b) he was pretty smitten and I didn’t want to hurt him.

She reminded me that continuing with him for any longer, after my gut told me I should go, would be even more hurtful.

My mind was made up.

I pulled the “hey can you come over to talk after Liam goes to bed” card, and despite a winter storm, he showed up at the requested time. He knew something was up and inquired right away.

I had uncharacteristically not worked out exactly what I was going to say, but I dove in. I told him I didn’t feel the way I should at this juncture of our relationship. That while some of my issues were Tony-related, and I knew we hadn’t had a lot of time to have “normal” dating, given my injury, it wasn’t just those two aspects. I told him I knew he felt strongly about me and I didn’t think it was right to continue when I wasn’t sure.

He was full of bravado, saying “don’t worry, you won’t hurt me”. He said he knew I would miss him and that I would be back. He asked how much of it had to do with my worry about staying monogamous (I said not much, which is entirely true).

He told me he thought we were always a “half step out of sync” which I thought was a great way to put it. But his version of out of sync and mine were different. He wanted to work on things and thought our trip would have been much smoother had we gone in another few months after we’d had time to actively date more.

I didn’t know how to tell him that us aligning on whether we’d play beach volleyball together wasn’t the kind of out-of-sync I was talking about.

He said he thought I was incredibly intelligent and he knew he wasn’t.

He told me that I threw him off when I asked him about exclusivity on the trip and askedΒ  was my boyfriend, implying that I was the one trying to move things forward.


I asked if he thought of me as his girlfriend after he told me he’d assumed we had been exclusive for a while because he knew [read: assumed] I wasn’t with anyone else.

It was confusing to me but I realized when talking to Hy again afterwards, that I experienced what “dumpees” often say when they are being dumped. He tried to argue me out of breaking up, saying he felt our out-of-sync issues could be worked on. I countered that I wasn’t sure they should be at this point, and I wasn’t feeling the way I should.

He came up with lots of counter reasons I could be feeling this way – none of them about him and my compatibility. He bargained with me, asking me to give it a month and to not date anyone during this time. I was pseudo-committal. I’m going to do what I want to do, but I’m also traveling a bunch in the next few weeks so no point arguing over something that could hurt him and be moot anyway.

He told me there wasn’t anyone like him, I was going to miss him, and he guaranteed me I will be back. I asked him if that was just bravado speaking and he was self-aware enough to smile and say “yeah, a little.”

I will admit, when giving him a kiss and hug and saying goodbye, a seed of doubt was planted. I am trying to stick with my gut on this, but it’s countered by knowing Leo is such a solid man. He would treat me very well. But I don’t know if it’s enough.

Perhaps a month from now I will miss him terribly and want him back. Perhaps not.

But for now, I’m single again.


Image from the 1955 movie “Stella”

17 thoughts on “Vacations are the kiss of death for my relationships.

  1. Well i did sense that the sparks that should have been present all along just were a flicker with Leo unfortunately.
    Hy is right that it’s best that you did this sooner than later.
    Maybe he’s in denial that you really don’t feel it with hm. IDK
    Onward Ann…
    Do what makes you feel good and happy.

    • I don’t think he’s in denial, I think he’s proud and confident and he knows what he has to offer, which is a lot. He also knows that my last few relationships haven’t ended well and he’s a stand-up guy. I also didn’t really get into the specifics about what I was concerned about, because he didn’t ask and frankly they aren’t things one can particularly work on. It would be like someone saying they didn’t like me because I was smart, or analytical, or curvy, or that I’m continuously trying to improve me and my life. I can change my behavior but I can’t change my core makeup.

      Perhaps with time I will get clarity and space in my heart and change my mind. I know he may not be around if/when that happens and it’s a risk I had to take. I needed to be true to my doubts, I guess. Thank you!

  2. As always I’m on team ASV, and I look forward(when you’re ready) to read about the rest of the the journey. I feel badly for Leo, but if he’s a confident man as you say, he’ll bounce back and continue in “his” own journey.
    For now, I’ll send my wishes to you both and await the next chapter.πŸ™‚

    • Leo will be fine, I have no doubt. I didn’t write our whole conversation but he said he wanted to remain friends. I said I don’t usually try to build a friendship after I’ve dated someone. But I’m not worrying about it either way. Thanks for your unwavering support πŸ™‚

    • Ummm… sounds like lots of judgment in that statement there, Johnny (or is it Jodi?). Leo and I weren’t exclusive so I could have sex with whomever I wanted. And no, I don’t tend to use the term “single” if I’m dating someone with an eye to a potential relationship. I just say I’m “dating”.

  3. I’m sure you’ve answered this before, maybe even from me, but… Is it your plan, when you find “the one” to make your future with, to inform him about the blog?

    I know this is a strange time to bring this up, but I was thinking about how a proud, confident man like Leo would react. I can’t imagine you with any other type of man!

    • Yes is the short answer. I’ve decided to not tell anyone until we are well down the path of a relationship. As you know, knowing about the blog has never ended well for me. Depending on the situation I may even shutter this one and start something fresh. I will sort it out when the time comes.

What do you think?