Another Midlife Dating Adventure – Ian the Octopus

You know that tingly feeling you get when things are going well? The warm sensation in your stomach (or loins), the flutter of hope that maybe this one might amount to something worth having or worth keeping?


I had that feeling at a key point and thereafter, while chatting with 52-year-old Ian on POF. It wasn’t instant. He grew on me and within a short time, after he’d installed kik so we could chat in relative harmony there, it happened.

I can remember the moment exactly. He’d slept an entire day after a mammoth Saturday at work that started frighteningly early and ended in the arctic winter hours after 7.00pm. He’d stayed tucked up in bed all warm and cosy the following Sunday, and I’d asked him how he’d kept himself occupied while awake.

Stupid question really – but any woman knows that if the can of worms is going to be opened by the mention of words such as ‘bed’, ‘naked’ or obviously, ‘sex’ we might as well cut to the chase and get it over with. At this stage of my dating journey I’ve pretty much lost interest in sexting or sexy talk via text. Especially unannounced dickpics. For a couple of years there I gave sexting and erotic tales a red hot go, but now it’s a case of ‘yeah-no’.

You could say it was a bit of a test by asking a leading question, and I was mildly pleased when he didn’t rise to the bait and immediately switch the conversation to a dick pic or boring assertions about how much he’d like to have me between the sheets.

After a bit of back and forth, he asked me my favourite things to do in bed when not in the land of nod.
“That would be reading a book, unless I had company,” I said.
“And then what would it be?” he asked.
“Then it would be lots of kissing, touching and exploring sensuality together.”

There was a noticeable change in mood between us and our exchange heated up a few degrees. I sensed that I’d touched a nerve or a strong desire for intimacy, not just sex, but genuine physical intimacy. This is emphatically what I want. I am directly my energies towards finding a partner who can meet my needs for a deeply satisfying emotional and physical, sensuous connection.

And so when Ian became slightly besotted by me after this point, naturally I began to think that perhaps he might fill the gap I’d created in my own mind for a potential partner. A step up from lover, and a whole ladder up from a sex date.

We chatted daily on kik, and I was pleased that he wasn’t the kind of guy who wanted to (or indeed, could) text all day from work. I wanted to save some of that energy and conversation for the real thing. I made two suggestions to meet face to face; the first he agreed to without actually getting out our diaries to find a date, but the second he committed.

A Friday evening at a local hotel (in other words an upmarket renovated old pub) not too far from my house was the time and place set for our rendezvous. It was a long drive after work for him on a freakishly stormy, filthy winter’s night. We messaged a couple of hours before to check in and yes, it was still on.

I felt unfamiliar nerves. This was a proper date – night time and at my request it was drinks, not dinner – and I dressed carefully with an eye on how he might perceive me. I’d said to him previously that I wouldn’t want to disappoint him, based on his imagination going into overdrive after seeing a few photos of me.

He was obsessing over one particular photo of me in a tight, black tank top in my kitchen, all hot and sweaty post dog walking. He hadn’t asked for any further pics and especially not any nudes, so that was a good sign. I’m so over those guys and I didn’t want Ian to be one of them.

I arrived at the hotel and saw him waiting for me by the back entrance, where we’d arranged to meet. I’d seen three or four photos of him, but he still looked like a stranger because in the flesh everything is different. He was shorter than I thought (definitely not 5ft11 as he’d stated). He looked smart and clean and I liked him immediately.

We smiled like Cheshire cats and greeted each other with wide open arms. Straight away he kissed me on the mouth and we melted together for several glorious minutes. It was a genuine, passionate welcome – and boy could this guy press my buttons! I was there, believe me, feeling those soft lips and that exploratory tongue. The pheromones were in overdrive!

I’d decided to change my MO and this time, be totally myself, no holds barred. Not that I’m ever a cold fish, but often I am reserved and I have a certain front, as we all do. Mine is self-contained, polite and friendly.

I know I can be intense and freak some people out when I’m on an emotional high. When my connected, super-power Gregarious Introvert is in full swing, I can be charming and extremely tactile. This time, I wanted to be tactile, in fact I couldn’t stop touching him.

I was thrilled that he totally reciprocated. For our entire three hours together our skins were never apart in some form – holding hands, stroking hands, stroking my skin in intimate places. Through our clothes – since we were in a public place – stroking our backs, our legs, even our faces. It was an incredibly charged evening of pure touch, the highlight of which was the sensuous and passionate kissing.

We’d made a beeline for a small intimate room with a log fire, soft armchairs and a couch. Of course we nestled on that couch and got to know each other, interspersed with kissing. He was demonstrative, affectionate and it felt amazing. I was most definitely in an elevated mood, letting down my barriers and throwing all caution to the wind. I was letting him see a genuine, direct and fearless version of myself, helped along by the gin-and-tonic he’d bought me.

“I can see you’re not used to compliments,” I said, nuzzling his cheek. I knew he’d been married for close to 30 years and that this was his first official date as a separated man of three years. I asked him when he’d last had a compliment.
“Twenty-eight years ago,” he said drily.

He was indeed a fairly typical, shy Aussie male. Married very young, with four kids mostly grown up, a civil but icy relationship with the ex, a middle management job in a factory that bored him, but one that he’d stuck with for three decades.

We had almost nothing in common, but it didn’t seem to matter, because we had this! These sparks flying off us, this song in my heart and this thrilling softness, a mutual lingering of tender kisses and interplaying tongues, a physical connection that I have so rarely felt.

Oh we did talk of course, and I did most of the legwork (no surprise there). It was flowing but definitely fuelled by the physical bond. My feelings of warm, fuzzy wellbeing enveloped me.

Even when we sat in separate chairs because the couch was so bloody uncomfortable, we both instinctively reached out to hold hands and pushed our chairs closer together. His hands did wander and the strange thing is that I did not mind one iota! His hands on my breasts and playing with my nipples through my dress were exquisite. He knew exactly how to arouse me both with his mouth, and his fingertips.

During several make-out sessions he even slid his hand inside my bra, while I moaned quietly in his ear and giggled. Later we both laughed about security cameras in the room – I hoped there weren’t any!

Once, while we were talking about something fairly mundane, he pulled me to him and held me close in a tight hug for a full two or three minutes. Then he nestled silently on my neck. It was an intimate moment that led me to launch those tender hopes. Maybe this one, this attractive age-appropriate guy, might evolve into something good, a worthwhile relationship that we would define on our own terms. Our kids were at a similar stage and though he was an active dad with a busy job, we decided that we could potentially share Friday nights and Sundays together.

When we grew tired and the hotel began to pack up for the evening, we headed for our cars. Just one pash goodbye was not enough. His hands wandered freely over my body, squeezing my breasts, my arse and holding me so closely to him that we both laughed in vocal arousal. We made plans to continue during part two, tentatively arranged for the Sunday.

“I’ll be dreaming about you tonight for sure, Silky,” he messaged me at home. (Silky was his brand-new pet name for me, which made me chuckle every time he used it).

We texted some more before I headed to bed, still on a high, to dream about him, and to cautiously hope for something deeper to develop. It was looking good, the signs were there, the passion was there….

And so you’ll understand my confusion and disappointment now – even my irritation and disgust.

What sort of a person behaves like this and then ghosts – disappears without a word?

How hard is it to say, “I’m sorry but things got out of hand and I’ve changed my mind.” Or, “I thought I wanted something with you but I’ve realized x, y or z and it won’t work.” How hard is it to do the decent thing and just tell someone that what’s just begun is in fact, over already?

Clearly it’s too difficult for Ian, and that’s what hurts.

I gave him a piece of myself, he took it, lapped it up and filled his need even if just for a few hours, and then he shut me out and pretended that I don’t exist.

It didn’t happen immediately. That Sunday he’d had to run errands with his kids and by the Monday evening I felt that the reduced frequency of texts and the lack of a response to my message (when I’d put the ball in his court to make the next move) was significant.

I felt it in the pit of my stomach that something was wrong, and sure enough when I checked on him over at POF, he was active on the site. I sent him a cheeky message, deciding that confrontation was the clearest approach. “Should I assume that you don’t want to see me again?”

A few minutes later he quit out of the site, so I didn’t know if he’d read it. I left it another day then decided to text him direct, asking him to at least tell me if he’d had a change of heart. Nothing.

I’m a big girl, of course I will cope. But it’s a low blow to be so disrespected, especially after sharing an intimate part of myself with him.

All the signs were there, so I’m left wondering what his side of the story is, and whether I did anything to cause this disappointing Radio Silence. What’s worse is that he’s blocked me on Plenty of Fish and his profile is still active.


Note: Names have not been changed, yes he really is called Ian. I think he’s forfeited the right to a pseudonym!

Note for Aussies: The really scary thing is that I’ve realised in hindsight that Ian is a dead ringer for our prime minister!

47 thoughts on “Another Midlife Dating Adventure – Ian the Octopus

  1. I wish our prime minister were a dead ringer for our prime minister.
    I’m sorry you got led on like that.
    I would have to say I did something similar to someone once. We had an agreement on a few boundaries and she broke them after the first date and started making plans to leave a bad relationship through me. I probably shouldn’t have gotten involved to begin with. I did like her but her ability to go back on something we had mutually discussed, and so easily, was very unattractive to me.
    *insert gratuitous cat story here* yes she also started talking about being Cheyenne’s new owner after that first date. I don’t really care how much her husband paid for that date and my gifts on his card but she does not get my avatar of Bastet.

    Liked by 2 people

      1. Probably more empathy. I can relate to being let down in courtship because the other person is more interested in their idea of what they want rather than accepting of what is. I am very happy to make a friend… ie if I like someone I don’t need to have sex with them. Being a non drinker I find a lot of dating boring. I have no issue with a friend having a few drinks but if I wanted sex I would be better off sleeping with a worker who is professional. I have no interest in taking advantage of someone. Sounds like another liar etc… is out there. In light of some of the things happening to women lately in this country I am a bit over these blokes who quite clearly hate women yet demand something from them. If you love something set if free et al… I always thought.
        Over dickheads.. and just yesterday was quietly thrilled that I no longer do any work inside of a football club.
        Rant over.
        Because I haven’t drank in 19 years they treat me like a wowser yet I see them drink and it really is pathetic. I would have spilled more than they have ever drank and I didn’t need to take a hostage to clean up my crap.
        Sorry you had someone do that to you. Take solace that there are people who respect and you no one anything x

        Liked by 1 person

  2. People are weird and rude. Middle aged people come with a truck load of emotional baggage and that makes them extra weird and often they do stupid shit without even knowing why. Ian is a dipshit and you dodged a bullet. Malcolm Trumbull is a shadow puppet in the vague shape of a prime minister.

    Liked by 5 people

  3. Urgh. This has happened to me a few times. I think this is what has happened with MG. I’m on the verge of removing him from all my social media. It’s confusing. I don’t understand why the ones who seem so genuine turn out to be the worst. I guess that’s their skill. Or maybe they just don’t have the balls to explain themselves if they have second thoughts. Who knows.

    Liked by 2 people

      1. A friend reminds me constantly, people deserve nothing. People will do what people do and I can either accept that or fight it but it is inevitable.

        I betrayed C. She hasn’t spoken to me in seven months. After seven years what do I deserve? I live in constant confusion about what to do next.

        Liked by 1 person

      2. I haven’t seen a response to you about where to start your story. Give me a hint as I am really interested to read your blog but I don’t know where to begin. I’m sorry to hear about your turmoil. That must be paralyzing.

        Liked by 1 person

  4. In reading your latest blog entry, Eve, I too would have to wander what this guy’s game was. Of course, as you probably know, you can’t always believe every little detail that a guy tells you when you first meet. The fact that you two seemed to hit it off bode well initially but this guy might be the type that shuns commitment but is attracted only to the chase. Maybe he was married and had kids, then again maybe not. Maybe rather he’s a confirmed bachelor who just likes to be “entertained by the ladies”. Or maybe he sensed that you were more serious in him than he was in you. Or then again maybe he is still married but his wife is not all that emotionally into him anymore, preferring him to go out and “amuse and entertain himself” with other ladies but still promptly return to the “royal household” afterwards (to take out the garbage and what not).

    Who knows his reasons and really who cares, right? (although I can assume that you did there for awhile). Bottom line, at least thankfully he didn’t lead you on for too long and then really break your heart later on. Agree? I do understand though your feelings of frustration and probable anger at having wasted your time and attention on such a loser. And so life goes sometimes, eh? Keep smiling nevertheless.

    Liked by 3 people

    1. Thanks Rob, you are a sweetie. I agree that I’d rather know after a week and a half and one night, than a long lead up – one of the reasons I prefer to meet as soon as possible. I did wonder whether he told me some lies, but I do believe his life story, I just think he had second thoughts but couldn’t be bothered to tell me, or didn’t have the guts. Onwards and upwards 🙂

      Liked by 1 person

  5. That is what is horrible about vulnerability: you take the risk, face the uncertainty, and be emotionally (and physically open) and you will get hurt. As a result somewhere along the line in stopped being vulnerable. I desire the thing I avoid.

    Of course, when I describe what I need and want in a partnership it demands that exact vulnerability. Instead I seek out safety. But safety and vulnerability cannot exist in the same spiritual place.

    What you did was incredibly courageous and brave…and beautifully vulnerable. He gave you lots of signs your vulnerability would be respected.

    His loss.

    He disrespected your gift as I disrespected C’s gift.

    I’m sorry.

    Liked by 2 people

    1. Thanks RC. That is a deep response, and though I may re-think the ‘no holds barred’ approach, I don’t regret it. I had a strong feeling that I needed to be that person in the first meeting, and so I was. I agree that it’s his loss. Showing vulnerability or raw affection is always a risk, and I think meeting Ian was a reminder that life’s too short to play games.

      Liked by 3 people

  6. What an idiot! His loss TOTALLY. I’m glad you were just yourself though, and got lots of kissing and touching out of the date- that’s good for you. Obviously he’s an emotional coward, so steer clear- you’ve saved yourself some drama. I’d have been wary of a guy on his first date out of a long marriage though…

    Next! Xxx

    Liked by 2 people

    1. Thanks G. I didn’t know it was his first date since break-up, but good point. He did say to me during our texting lead up, “Thanks for making me feel things I haven’t felt in years’, so maybe that was a warning. But I missed it!

      Liked by 2 people

  7. Oh mate, TOTALLY feeling this right now! This was such a great read – I was so excited for you! Then so devastated! Great gut wrenching writing- thank you! So many familiar feelings, especially the intoxicating “maybe THIS one” feeling. I can also relate to re-evaluating the ‘no holds barred’ approach. I’m wondering how to have integrity but still hold a few cards to your chest, if such a balance is even possible.

    Anyway, I’m glad you had some sensual moments, and I’m sorry they didn’t bear fruit. Thanks for sharing your thoughts – sending solidarity x

    Liked by 1 person

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