Real stories about dating and relationships in New York City. Truth is more interesting than fiction.


Stories are shaped by the way we tell them. There are the facts, and then the way we present the facts. Our attitudes and prejudices.

I could tell this story a few different ways,  each with it’s own spin. I’m not sure which would be right.  Instead I’ll just try to throw it all out there.

The basics: I’m not going to be seeing Mr. Midwest anymore.

He’d emailed me on Friday and asked about my plans for the weekend. I replied I was free Sunday night.  He didn’t reply. Rather, he called on Sunday morning with suggestions for things we might do that night. These he left on my voicemail as I didn’t answer the .  I wasn’t, at the moment he called, sure how I was going to deal with it.

A part of me thought I should ‘play the ’.  Tell him I’d made other plans since I hadn’t heard back from him. But doing stuff like that makes me physically ill (and in fact I was nursing a stomachache over the thought of it- no joke).

A part of me thought I should call him and tell him I wasn’t interested in seeing him anymore. I could stand being ambivalent about a , but only if he’s acting as if he really likes me.  The shift from frequent calls to unanswered emails made Mr. Midwest seem suddenly less attractive to me.  My ambivalence had potentially turned towards dislike.  Potentially.

And a part thought I should just go out with him again and try to initiate some kind of ‘where are we, if anywhere?’ conversation on the date.  Which I felt was probably unfair to the both of us.

In the end, I called and told him that I’ve enjoyed spending time with him but felt that we hadn’t really made much progress in getting to know one another. And, thankfully, he jumped in and agreed and said it seemed like we just weren’t connecting. So we talked about that for a few minutes (talk about awkward). And I mentioned that maybe we shouldn’t see each other anymore.  That maybe we just weren’t going to connect.  And he suggested that we get together for dinner and try talking some more. Connecting.

Then I jumped in and suggested that he invite me over to his place. I thought it would help (if the situation was one that could be helped). At which point things got more awkward. He got really panicky and started to stumble over words.  So I tried to take it back, saying that if it was something he wasn’t comfortable with I understood. But he insisted (it was the most hesitant sounding insistence I’ve ever heard) and so the plan was I’d go to his place for talking and take-out and he’d text me the exact address.

Less than 30 minutes before I was supposed to be at his place, I was putting on some makeup and trying to figure out the appropriate next step if he didn’t send his address (4+ hrs had passed since we’d spoken).  Then the phone rang and I knew. He was calling to cancel. To end things.

He was extremely sweet and polite.  He said he’d thought more about what I said and thought that maybe we were trying to force something that wasn’t there. I said that was very possible and that it was probably better (if we both felt that way) that we nipped it in the bud.  And he asked if we could stay in touch. He even joked about setting me up with one of his friends because I’m so cool.

It was all very pleasant and mature.

Yep, pleasant and mature.  That’s one way to look at it.  Or you can imagine that my request to come over to his apartment was the end of the road. That he was hiding something.  That would be the cynical spin. I’m not inclined to assume every guy is a lying asshole (despite the name of this blog) and so this doesn’t ring entirely true to me.  But it sure seems possible.

Or maybe I just blew a potentially great thing.  Maybe if I’d just kept my mouth shut a little while longer we would have started to connect. That’s certainly possible.

I don’t know where the real truth lies. Other than in the basic facts – Mr. Midwest and I went on a handful of dates. We enjoyed spending time with each other, but it felt kinda empty.  And now we’re not seeing each other anymore.

I’m not sad about it.  I will, however, take the week off from dating.  I’ve got lots going on with work, and honestly, just need the break.

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28 to “Finale”

  1. KB IN NYC says:

    Simone darling, you just can’t beat yourself up about it. I feel your angst though because I do the same thing – maybe I shouldn’t have said this, perhaps I should’ve done that. Maybe, just maybe, things could’ve been different! But you know, you went with your gut. You did your best sweetie and maybe it just wasn’t meant to be. Simple as.

    Definitely take the week off, do something for yourself. And keep the faith.


    • Simone Grant says:

      Thanks honey. I’m really not beating myself up. Just pointing out, I guess, that there’s no way of knowing if I did (or didn’t) do something to mess things up. Life’s like that. I think it wasn’t meant to be, and we were both trying to force it because we liked each other a bit… And maybe, in another time and place that would be enough.

  2. Jolene says:

    Bummer – but I think it was the right decision, from reading about Mr. Midwest. No connection at all after a few days – onward…right?? 😉

  3. Lara says:

    time off, pampering yourself, breathing = a VERY good idea! Enjoy!

  4. I think it’s amazing that you keep getting back on the horse. Take the time you need, I say.

  5. jane says:

    Hug to you Simone, may don’t used online dating anymore, finally I found my guy not from online dating.
    I felt guys used online dating only for entertainment.

    • Simone Grant says:

      Some guys online aren’t serious. Lots are. I know a couple of male friends who’ve met their gfs online.
      I don’t think I’m ready to give up on it quite yet.

  6. Manisha says:

    Hey Simon,

    I have been stuck in an exact “relationship” with a guy for 3 yrs trying to make a connection.I tell myself everytime he comes around that maybe this time he’s back for good and we can build from hereon. But Im always left disappointed. He always has an excuse ready to step back. He’s a really nice guy but I’m tired of this tug of war of sorts. I finally decided to walk away last week FOR GOOD, without explaining myself. No matter what we discuss, Im aware of the fact that we just dont have a connection. And if its not now, then when?

    You did the right thing!

  7. mel says:

    Tough spot. Sorry this one didn’t go so smoothly. But enjoy the time off! It may be just what you need.

  8. Eh, you never seemed too excited about him. Why he would freak out about you coming over, other than thinking you were after his junk, is beyond me. But boys are weird. I say take all the time you need!

    • Simone Grant says:

      Like you said, boys are weird. Maybe his apt was messy, or he didn’t want me to see where he lived, how small his apt was, how big his apt was – who knows.

      And yeah, I was never that excited about him. It could have been good, if only…something.

  9. pups4me says:

    Him not wanting you to see his place has red flags plastered all over it. Maybe I’m cynical too, but I’ve done my share of dating (still at it) and if I can’t see a guy’s place by the 3rd or 4th date, I sense something is not right.
    I think it’s important to check out where a guy lives, as it gives insight into the type of person he is.
    Don’t beat yourself up about this one and enjoy the week.

  10. Sandyvs says:

    ALWAYS go with your gut feeling. Don’t EVER question it. You mentioned in an earlier post that you’d suggested takeout at his place and things went south, and now the same thing happened again. (Insert ANY excuse you can think of here that he would use for not wanting you at his place, and the reply would be: This is not going to work out and this is not the man for me). Don’t think/worry about this one more second. Next!
    I’d give you a hug, or pat you on the back, but I don’t think you’re that torn up over this one.

    • Simone Grant says:

      My gut hasn’t been so smart in the past and so I have some trust issues with it. It’s going to take some time until I feel good about going with my gut again, but I totally appreciate what you’re saying.

  11. Ian says:

    “Maybe if I’d just kept my mouth shut a little while longer we would have started to connect. That’s certainly possible” … No it’s not. You gave him every chance. Next!

  12. Simone Grant says:

    Thanks. Maybe the next one will come with all kinds of surprises. I like surprises.

  13. Leah says:

    Hi Simone, I just started reading your blog a month ago. I love reading your dating stories. Most of the time I can really identify. This weekend, I couldn’t wait for your next update on the Mr. Midwest saga, and checked this blog like 5 or 6 times just to see if you’d updated. I wouldn’t feel bad about Mr. Midwest, sounds like he wasn’t the guy for you from the beginning. I definitely agree with the other comments that you did the right thing :)

    • Simone Grant says:

      Thanks so much – for reading and for the lovely compliment. I don’t really feel bad, just kinda tired of meeting these perfectly nice men who like me “sorta” but aren’t the ones for me. Seems like a cosmic joke.

  14. Whitney says:

    I just went through the saaaaaame thing!! Me and the guy decided to keep talking and give it more time but we just aren’t connecting…. We are great friends, encourage and motivate each other but that’s it… I recently started seeing someone else… I’m now wondering if I should tell him or just leave it be…

  15. Kam says:

    You did the right thing – you followed your instinct. What exactly is he hiding at his place anyway??? He obviously is holding back something, and the connection wasn’t there in the first place. I just hate you had to get dressed up before he cancelled!

  16. Jasmin says:

    Simone, i have similar experience as yours, i think this guy is seeming someone else too.
    I met a guy went out for a month. He seems like so honest, very genuine, never broken his word. I respect him for this reason. We have lots in common, he found me sexy, so the physical attraction is there. He talks about what we could go for walk later. The one thing annoyed me is 3 weeks ago he ask me out for walk on sunday, week after he didn’t make plan, he then take me out for dinner on Monday, week after is long weekend, he ask me if i am free on Monday, he said he got a few things to do on weekend. So i email back that i don’t feel he is keen enough. He still text me on Monday which i ignored, i email him that i am not his back up plan. Then i regret, because i didn’t confront him before i make assumption. So i called him without respond. He just disappeared. If i were him, i would say: lets just leave it as it is. So i can tick off from my life. One way i know i did right thing, another way i am kind of regret being emotional without ask him first. Lesson i have learnt :-)