50 First Dates | April Edition

The concept of too many first-dates has crossed my mind lately.  I have been on a lot of first dates.  So many so, that I thought it might be fun to actually begin counting them.

Trouble is, when do I start counting from?  I am single for going on 2 years now…I don’t even know if I could remember all the first dates during those two years!

Then, I figured, why not just start now? This blog is a fresh start so why the heck not?

So, starting in April, I will start counting all my dates, for better or worse.  At this moment, I can’t say that I have much enthusiasm for dating, but I have started having more sex!  I think the tides are turning and I plan to be having more casual sex now that I’ve managed a few romps without any tears or regret.

How many first dates is too many first dates?  At what point should I stop having all these first dates?    I know for certain this is a whole lot less random dating than I did last year (so far), and I take that as a good thing because I am much more discriminatory with who I am dating.  When I make the first date, I assume there is potential for a second date.  So far, I haven’t made any dates just because I think the guy is hot and I can sleep with him….but I am certainly about to start that up in May.  I can’t focus on a boyfriend and job search at the same time.

So casual fuck time it is.  Am I ready?

Here was April’s lineup:

  1. 98% OKC date: semi-fail, date was ok but he hasn’t asked me out again even though he stays in *rare* contact.
  2. Silver Haired Gentleman: A decent start that flopped quickly. A bit weird.
  3. 94% OKC date: Electric sex on the first date, but it ended there, at least, I think so.  I’m actually not sure.
  4. 99% OKC date/Mario: lovely drinks on the first date, and I was totally crushing on him, but he’s a douchebag.  He’s a douchebag I have every intention of fucking.
  5. Random Bumble encounter: one and done.
  6. Finnian:  a dark horse this one, such a surprise.
  7. 95% OKC date: an out-of-towner that couldn’t kiss properly, he’s not gone entirely.

7 first dates in April,  2 second dates.

All in all, I can’t complain.  The most significant effect this month had on me was finally knocking Bobby out of my head (maybe not for good, but certainly mostly).  It feels better to have that emotional real estate back.  I was leasing it to him for way too long.



Author: Madeline Harper

My journey through divorce and an emotional and sexual reawakening. Love, laughter, friendships, family and heartbreak included. And there is sex, lots of it, so close your eyes and turn the page if that's not for you! While I started this blog as an endeavor to journal my thoughts and feelings in an attempt to better understand myself, it has become an amazing platform from which I have met some of the most interesting and wonderful people in my life. My path is often crooked, but I hope you will share in the journey with me.

18 thoughts on “50 First Dates | April Edition”

  1. Is it the number of first dates that really matter or the number of dates that may come afterward? When I dated between marriages, I had a lot of first dates (and lots of sex on most of those first dates – yay!) but only two second dates – married the woman I had my second date with so I obviously didn’t need any others.

    I ask because it’s said that you only get one chance to make a good first impression and while this is true, for you, does a second date give you or someone a chance to improve that impression or if they fail to impress at that first date, you may not be open to give them a chance to improve?

    I read what you’re up to – haven’t commented lately until now and I apologize for that – and it seems that a some of the guys you’ve been dating lately somehow manage to kick themselves out of contention (the fools) by not doing the simple things, like staying in touch and being willing to have that second date.

    So do you really want more second dates, third dates, fourth dates… or are you just looking for good quality first dates to get more used to the casual sex thing? During one reading, I thought that if I ever got a chance to meet you, I’m bringing a case of prosecco with me…

    Liked by 1 person

    1. See….this is where Finn is smart…he gets the Prosecco too! 😂

      I want second dates, for sure. And, even a few of these I would have tried second dates and it didn’t go there.

      Right now in my frame of mind, I don’t know how much dating I can manage but hate to eliminate sex.

      I’m so glad you’re back Kdaddy!


  2. I think you answered your own question about how many first dates is too many – when you stop anticipating second dates. Otherwise, doesn’t that mean than they stop being dates and just become hook-ups? Not that there’s anything wrong with that at all (in fact, go you!), but that’s the way I look at it.

    Liked by 3 people

    1. Yes, but you just articulated it better than I did – you are right, once I stop thinking there is potential for a 2nd date it simply is a hookup and no longer a 1st date.

      My other question (to myself) would be – why do I have so many first dates just to find a suitable dating candidate? Am I just too picky? Or not really ready to date?

      And, btw, very nice to meet you Roses 🙂 Welcome


      1. It’s a hard question to answer – I confess that your post has me thinking and working on a post of my own with a similar theme (don’t worry, you’re credited 😛 ). I would not say that you’re being picky at all. Just not ready to settle on one person maybe.

        And ta 🙂


      2. Perhaps you aren’t picky enough about he right things before you engage someone. Ideally you would have fewer first dates but with men who are closer to what you are looking for. But you have to be confident enough to not need a large volume of men in your pipeline.

        Liked by 1 person

      3. Give me an example of what I’m not being picky enough about – what are the right things in your opinion? I’m curious because every man I’ve chosen had possibility in my opinion. It keeps coming down to chemistry for me which I seem to be unable to move past.
        I’m not worried at all about a large volume of men. When I’m engaging someone I’m not back to the sites looking for the next…I wait and see how the current conversations go.


      4. Maybe it’s not about being picky in an initial show of interest, but one you are engaging them you ignore / dismiss / self-talk yourself out of recognizing red flags and continuing to persevere in their presence.

        Liked by 1 person

  3. Wow, I must say I envy you a bit, I haven’t gotten back in the dating at all. I hope I’ll be ready soon. Meanwhile, I read your blog and Ann’s, to live vicariously through your blogs when it comes to dating. 😉

    More on topic stuff: As long as you feel okay about what you are doing, no one else can judge you. We have a free society and everyone must do what is right for them. If you feel like a lot of first dates/casual sex, I say go for it! Listen to your gut and your inner voice. If at one point you feel that something is off about what you are doing, ask yourself why that is. You got this, girl! Best of luck. 🙂 xo


      1. Oh no don’t be sorry.😊 I do appreciate the sentiment though. Am just a bit battered and bruised in my heart but I will get back in the saddle eventually. Your blog inspires me to dare to do that one day… I do not agree your blog has been a shot show, the way you write it makes it very exciting to follow!
        Take care and be well. 😊

        Liked by 1 person

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