A Dating in Midlife Adventure

One man’s search for sex on tap, a full belly and a roof over his head

Within the first half hour in his company, 50-year-old Simon told me that he’s looking for a good cook and a regular sexual partner to meet his daily desires – he prefers oral over penetration because the old fella doesn’t work so well anymore, and he’s got a bad back. He’d like a blowjob every day and if he likes the smell of me, he’s happy to pleasure me in return.

Later, on my drive home, I decided that despite his generous offers of near-constant orgasms (assuming of course that I met his olfactory standards), the guy was living in fantasy land. He also lived too far away from me and had an unreliable availability pattern due to working on demand in a low-paid service industry.

In short, Simon was a bad match despite our chemistry, which undeniably did exist. The way he’d brushed my nipples and when I allowed him to briefly explore my naked breast, his fingers knew exactly what to do to make me gasp.

I should have listened to my instinct when we first connected a couple of weeks ago on Plenty of Fish.

I’m making a strong effort to meet and give chances to men in my age bracket, or even a little older. This cougar’s trying new tricks because the young ones are problematic, to put it mildly.

Simon’s profile photos showed an attractive mid-life guy in good shape, with a winsome, hippy-flavoured user name – plus 16-year-old photos of his heyday living on an African commune wearing sun-bleached dreadlocks and just a pair of skimpy shorts over his all-over bronzed tan. (What was that about? Imagine if I posted photos of the same vintage! And why would I?) We’d shared an opening line each on POF and then he disappeared for a week.

Our next messaged conversations were disconnected and jarring. After his brusque request for more photos (I already had six uploaded), I deleted his thread and moved on to other conversations.

Simon was persistent and returned to our conversation, asking why I had disappeared. I told him frankly that in my experience if a guy immediately asks for more photos, what he really means is ‘show me your tits’ or ‘give me a nude’. He backpedaled and so I decided to give him a decent go at convincing me.

We moved our messaging to kik and the awkwardness continued until I confronted him about his bull-at-a-gate attitude. He seemed to expect that he could achieve the delicious highs of smitten new love immediately, with little or no effort or time to get to know the other person and their authentic self.

“Are you new to this?” I asked. “You need to allow time to get to know someone – you can’t just have instant intimacy on a plate and happy ever after,” I said, feeling as if I was explaining the obvious to a kindergarten child.

“I know that, hun,” he said. “I’m not angry with you I’m just sick of this online dating shit.”

Fair enough, I thought. It is sometimes crappy and often frustrating, but that’s a naïve attitude to begin with. We managed to develop a tentative rapport after that, and seemed to be on the same page sexually, so I suggested we meet up for a coffee on my day off – a couple of days away.

The frost was still thick in the winter air when we met at the café and I noticed him watching me from his driver’s seat as I climbed out of my car. He looked like his pictures, which was a pleasant surprise, and as he hugged and kissed me on the lips I felt his enthusiasm.

I don’t actually like to be kissed on the mouth on first greeting – I find that presumptuous and invasive, but I warmly greeted him anyway, and we ordered our drinks. I insisted on paying for my coffee. He baulked, but I already knew he earned a lot less than I do, plus I didn’t want to feel obligated in any way.

As we nursed our coffees and talked, sitting on a bench under a historic, winter-bare oak tree, the feeble sun warmed our bones. I kept the conversation bubbling smoothly by focusing my questions on him and his rather interesting life.

As a citizen of three countries, he’d only lived in Australia for the past 14 years and his accent was a hybrid proof of his past. His manner was blunt and strangely detached, incongruous for one who claimed in his POF profile that keeping the honeymoon period alive was his greatest desire.

He felt no compunction about moving closer on the bench seat to fondle my breasts, and given our sexually charged texted conversation and my desire to build a regular sexual relationship (if nothing else, though that’s not my ideal), I didn’t mind too much. But I certainly noted that behaviour and his subtle sense of entitlement.

He hadn’t mentioned that he was father to a five-year-old until now, and he said that it seemed to repel women of his age, whose children were a lot older or who didn’t want the burden of a man who came with that sort of high-maintenance baggage. Next I discovered that he was a ‘Sunday Dad’ and his one day with said daughter fell on my one kid-free day.

And then he dropped the bombshell that fell with a muffled feathery weight. I’d been saying that a man’s kids were no concern of mine as I wasn’t looking for anyone to live in my pocket, or indeed to cohabit. Two decades of that were more than enough!

“Well actually,” he said, “I’m looking for a partner to move in with. Not right away, of course.”

The text comment about my cooking abilities floated into my thoughts, which I’d read as a bit of a joke. It now appeared that he was serious. He lived in shared accommodation, had a casual and unreliable job, and was desperately horny!

In hindsight I can see that from then on that morning, his attitude subtly changed. He stopped trying to nestle against me and the conversation remained firmly focused on him. During the entire hour and a half together he asked me one question – what I did for work.

While we strolled in the fresh air around the nearby park, he walked several steps ahead of me and didn’t turn to speak – commenting to the air instead. He pulled me into an awkward embrace on the pathway and cupped my breasts while kissing me again, but he didn’t linger, which seemed odd at the time – as if he couldn’t be bothered actually trying for authentic intimacy.

As we sat on a park bench in the sunshine, we kissed again and his hands wandered, but he barely listened to me speak as I responded to his question about my last serious relationship.

“Oh and I can’t do lots of positions,” he announced. “I’ve got a bad back and the little guy doesn’t behave himself sometimes. I really like to be sucked. I’d love you to suck me right now.”

I laughed at his boorish enthusiasm, while reeling at his gall. There was a peculiar feeling of harmony (sexual chemistry) juxtaposed with a complete disconnect around values, beliefs and what we were each looking for. “All good things come to those who wait,” I quipped. “Just be patient.”

At this stage I was still stupidly hopeful that we could become regular lovers, so we talked schedules and logistics, my mind on practicalities rather than the bigger issue of whether we were indeed compatible beyond the bedroom.

I was also quietly absorbing his revelations that his tackle wasn’t fully functional – something I am coming to see is extremely common in men over 45.

“While many women in their 50s and up say they feel more sexually liberated than they did in their 20s — finally released from the worry of getting pregnant, and more comfortable with their bodies — they are frequently tumbling into bed with men who suffer from erectile dysfunction. ‘I hear this from a lot of my girlfriends, and it’s depressing,’ writer Kerri Sackville said. ‘Finally, [they think] “I’m going to have great sex”, and it’s not working, and there’s nothing you can do about it.’” (Heart Ailments and Erectile Dysfunction: Life on the Dating Scene for Women Over 40, ABC, 4 October 2017)

As if this picture wasn’t depressing enough for those of us who like and are sexually attracted to men, comes the research findings that men who have regular sex over aged 50 may just be increasing their risks of heart attack.

“Because older men have more difficulties reaching orgasm for medical or emotional reasons than do their younger counterparts, they may exert themselves to a greater degree of exhaustion and create more stress on their cardiovascular system in order to achieve climax,” said Professor Hui Liu in the Journal of Health and Social Behaviour.

Simon kissed me goodbye and fondly patted my bum. I couldn’t help but feel it was an insincere gesture and sure enough, he messaged me a day later.

As I predicted, he’d decided that he was going to focus his attentions on meeting the woman who ticked his required boxes (sex, food, shelter). Sigh. It’s so boring when my intuition is right all the time. Just occasionally I’d like to be surprised on a date by someone who is actually great!

Onwards and ‘upwards’ for me – even if not for the men I’m meeting these days!

Interview with bone&silver

True tales over 50 (Love for self, the planet and that tricky teen) – by the infamous and wonderful, G

This is another in my regular series of in-depth and (hopefully) insightful interviews with bloggers who write on the topics of female sexuality, midlife adventures or dating in the modern age. You can find others here, here, here, here and here.

G of bone&silver

Firstly G, I’d love to know the backstory of your blog – why you started it, when, and what your goals were? Do ideas for topics just come to you or do you carefully prepare? Where does the name of your blog come from and what’s its significance for you?

My blog started as a motivator to write more regularly. I’d kept a couple in the past (one on puppetry, and one on dealing with the loss of my Dad, and whether to read his personal journals or not), but wanted more freedom to write about whatever cropped up. I started bone&silver in Aug 2015, as my son and I were about to travel overseas for 2 months, so I figured it would be a good communication tool for friends and family.

I don’t carefully prepare topics at all. I love spontaneity and the impulse of the moment, so try to follow the creative inspiration when it finds me; it can be an image, a feeling, a fellow blogger’s post, or an experience I’ve just had.

I brainstormed the name with a few creative friends, and love it so much! As it says on my About page, I write about the truths I feel in my bones, and am proudly a silver fox who refuses to dye her hair, because Ageism and ‘grey-shaming’ on women utterly sucks. I am proud to be authentically me.

Since that time, what do you think you’ve got out of it? The benefits and the challenges? What do you love about having a blog and so many loyal readers?

I’ve gained so much more skill and discipline in crafting good post. I just love blogging, and wish I could do it all day sometimes. I love the connection with other readers and writers, and the huge variety of topics I can learn about; I follow a wide spread of blogs and interests. Without doubt, I love my readers and regular commenters so much – they help and support me through deep challenges and fun times too. I’ve received such insights and care from my readers.

Because UTC focuses on relationships and online dating would you like to share some of your learning over the time you’ve been giving it a go? As an online dating veteran (since 2009!) you must have seen a lot, experienced a lot and made some changes in your approach or expectations over that time?

I began on RSVP, and quickly found it very conservative, and full of men over 50 who were possibly married and being deceptive. I found one treasure of a bi-man and we are still firm friends. A groovy online expert sent me to OkCupid, and I found my online dating home there in 2010! Don’t forget, I’m in Australia, so the dating pool is waaaaaaay smaller than the American one; OKC back then was full of all the kinky, poly, queer, open-minded, and fluid folk I adore. I had a fabulous time in that community, and encouraged many other women over 45 to join. Sitting passively at home wishing you were having more sex or romance IS A WASTE OF TIME LADIES: go out and get it. That’s my basic philosophy really. And I tell every woman who’s thinking of online dating to remember this: you are the prize at the top of the mountain, and people have to work their way up to you, rather than you selling yourself to them.

What is your current philosophy on dating, relationships and your goals now that you’re single again? Do you have any comment to make on relationship models and your journey, beliefs and what you’re seeking now and into the future? Has this changed much over recent years?

Currently, I just want fun, attention, non-monogamous connections, but always with good communication and mutual respect. ‘Having fun’ is a huge motivator for me. I get very excited by a wide range of relationship models, and have been exploring polyamory both theoretically and physically since 2011. Monogamy is easier, but kinda bores me after a while… I have no desire to ‘settle down’ and live with a partner, as I LOVE living alone, but having someone next door or down the road would be lovely. As long as there was a negotiated freedom for other connections, whether just sexual, or more emotionally-based. As a Feminist, I continually seek a sense of freedom from oppression, especially those imposed by the patriarchy or religious dogma. Stuff that.

Based on your experiences, what would you say about the differences between straight dating and other combinations such as same-sex dating? Is there common ground that is universal? What are some of the unique issues?

My immediate response to this question is of course unfortunately ‘safety’. I will meet a woman way more quickly than a man, and just feel less cautious and protective. I would be quicker to go home with a woman too.

Common grounds are definitely that we’re all looking for connection, whether just sexual or more involved. Unique issues for me are that women’s politics are generally the same as mine, as we have the same ‘lived’ experience in this world run by men, whereas men can be very diverse in their attitudes and presentation.

Do you think there are unique issues in relationship breakups between women? What are some of the stressors? Have you made any resolutions to stand by?

As a general rule, women will do a lot more mutual crying and expressing together. There is often an incredible sense of friendship and care, which can be complex to unravel from the ‘girlfriend’ connection. Women tend to get more intimately involved with each others’ female friends, so again there can be a challenge re loyalties and un-entwining. The only resolutions I’ve made are to try to be kind, yet also take good care of myself and my personal needs for healing, which may mean minimal or no contact for a while for example (I had to do this with one female ex, who just didn’t understand it at all- I even had to delete her from my Facebook to get some space) It depends on the emotional investment I guess, and the hurt being experienced by one or other of you. Mutual break ups are the best.

What are the challenges of writing about a relationship as it unfolds? What are your thoughts on the ethics of writing publicly about relationships generally? Is there a tension between the rights of the person expressing their truth and the rights of the person being written about? You write about a first meeting here, which is both funny and poignant.

Great question. For me, writing about my new online romance was part of the creative connection and inspiration I shared with my beloved ex ‘H’; I would write them stories or blog posts, and in return receive hand-drawn comics. From the very beginning, ‘H’ was clear that I had the freedom to use my creativity to express and explore via my blog; I did sometimes worry if I’d written too intimately, and would always have deleted if ‘H’ said so, but they were often the posts ‘H’ liked best.

Now that I’m dating new people, I am choosing to write about them so far in general terms only, and wouldn’t involve them in greater detail without a clear discussion and their full consent. As a mature woman and artist, I believe it’s my duty to reflect a positive ageing experience, which includes dating and sex, but I need to find the balance between respecting privacies, yet creating intimacy with my readers. It’s a fine line, and I admire bloggers such as yourself who go for more in-depth details.

How do you see the evolution of dating and finding a mate unfolding across the generations or the eras? For example, we are both Gen X women over 40 and I’m sure we have a lot of common ground in the challenges of being single at our age and stage. Thoughts?

I refuse to stay home and grow old + lonely on the couch; I love online dating, and the thrill of the chase. I’m certainly not looking for a life partner ‘to complete me’ though, as I have achieved a lot by myself, and love the life I’ve created. I have my awesome son, amazing friends like family, and own my own home. I have travelled the world by myself, and love my own company… it would be nice to have someone special to snuggle up with sometimes though, hence my online dating skills. I don’t necessarily believe in a ‘happy ever after’ with one person, but I do enjoy spending precious time and adventures with meaningful people.

You have used the phrase ‘the dating roundabout’ a few times – why is that? Do you think it’s like a roundabout with no one destination or …?

There are certainly patterns that I can see in online dating, such as signing up with enthusiasm, drooling over various profiles, sending out a bunch of messages, hearing nothing in return, and getting jaded by the whole process within a fortnight. In that way, it’s a roundabout, as I search, message, meet, decline/get declined etc. But I don’t keep going round and round mindlessly; I have learnt an awful lot, and when I feel like I need a break, I happily step off.

Your blog topics are wonderfully diverse and I guess the common theme is your interests and your life over 50? Tell me about how and why you started some of them, eg France and travel?

I got more serious about the blog when staying in France for 2 months with my son; we had lots of time to read and write, so I got into a blogging habit. As an artist, travelling to perform at festivals and events, I have a fairly interesting and unexpected lifestyle, so can always find something to blog about. I also live in a pretty quirky corner of Australia, near Byron Bay, so am exposed to lots of different viewpoints and experiences; I like to share new ideas.

How much does your everyday life inform your blog writing? Is there much crossover?

They are deeply intertwined! As a writer, I’m always noticing details, or finding story ideas in the way someone walks past me, or something I overhear in a café. And when I go through a personal drama or challenge, it is often mirrored in other blogs I’m reading, so I will reach out for advice or to offer empathy.

Your popular ‘Teenage son’ section has recently become controversial – I’d love to hear how that started and about the challenges of writing about our children once they become ‘of an age’.

Ha: ‘Controversial’ in that he told me to stop writing about him! He is an important part of my life (obviously), and quite a character, so to NOT include him would be difficult. The ‘Teenage Tuesdays’ just evolved as we were practicing driving on his Learner plates, and he kept saying funny things I would remember… but now he’s banned me from using his humor. I absolutely have to respect his privacy.

I’d love to hear more about your writing – goals and ambitions? Where you’ve come from… I like this piece where you talk about how important writing is to you.

I’ve always kept journals, as did my Dad. I’d love to write a book (or 10), but what about? What genre? Could I keep the discipline of working at it? I am an avid reader (my Mum was a librarian), but blogging’s immediacy seems to suit my personality best. Writing is definitely one very important way I process life experiences. I also enjoy the freedom to press the ‘Publish’ button without needing anyone else’s approval.

How much does your environment and location stimulate you to write or give you a focus for your blog?

Great question. My creative training is as a dancer, clown, and Improvisor; so being Here, in this Moment, is the major aim of all three disciplines, which easily translates to blogging about what happened this morning in the car, at the beach, or on the news.

How do your beliefs or convictions as a feminist, someone passionate about caring for the environment and sustainability, and performing/art intersect and connect in the blog and in your life?

If asked to define myself, the first word I would choose would be Feminist. Then Artist/dancer, then mother/vegetarian etc. I feel fiercely that we all need to honour and respect our only Earth, especially for our children and grandchildren; these filters are how I live my life, and I’d never change them. For me, they all feel right.

How does it help you to express and share a piece like the one about your father’s passing? Is it in the getting it outside of us, or the sharing that seems to help for you? Are there any downsides to writing personal tragedy or deep feelings?

Losing my Dad was a terrible shock, which rocked our extended family for a long time; expressing the rollercoaster of emotions that follow a death helped me experience that sharing is a way to dispel pain, to offer hope or advice for others, and most importantly to break down barriers around mental health or other taboo subjects. It also builds community, and reflects other’s experiences back to themselves as valid, unique, yet also universal. I often cry while writing deeper pieces, which feels good afterwards. As an artist/performer, some of my best performances are the ones which move others to tears, so to be able to do that with words is wonderful. We’re all here to connect and share our experiences I believe, so that’s how I try to blog; my readers’ comments are without doubt my most treasured gift from blogging.