Life in the Dating Fast-Lane: Dating an Older Man

Life in the Dating Fast-Lane: Dating an Older Man Briony Rainer

17th August 20162Comments
Briony Rainer dating advice

After the slow-fading, alien-loving fiasco that was the sole extent of my dating life last month, it was high time to have a good think about what I really want. With no dates on the horizon and in need of some fun, I took myself off to Oxford for a long weekend. I ate delicious food, chatted to lots of friendly people, found a couple of lovely pubs, walked and shopped. The thought that I wasn’t sharing this with either a friend or a partner didn’t even feature on the radar.

And if I could enjoy spending time on my own so much, do I actually want a partner? What purpose would this serve? I am satisfied with my life as it is, I am not lonely and I am rarely bored. I concluded that a cat would provide the occasional comforting cuddle when I feel ill or stressed; and sex is not too hard to find if I really need it. The man-search was officially called off.

Whilst I was on a roll with the self-reflections, I also made a plan for the next few years of my life. This involves a dramatic career change and going back to university for 4 years. Satisfied with my planning and excited by whatever may lay ahead, I went out for a solo glass of wine (or three) to celebrate.

Whilst in the pub, I had a message from Mr Alien asking me if I wanted to join him for a birthday drink a few days later. I had not met any of his friends during our brief dalliance, and thought that this was a fantastic opportunity to have some fun with a few made-up conspiracy theories of my own. Having made my friends promise to check me out the next day for evidence of cult indoctrination and anal probing, I agreed to go along.

I set off on the night wearing a tinfoil hat, which I think looked rather glamorous with my new top. Mr Alien’s friends seemed normal, and when they started to sarcastically challenge him about his theories I knew it would all be fine. I spent most of the night chatting to one particular friend and having an absolute blast. He was a much older man – my best guesstimate was about 20 years older, and I thought it was rude to ask – but after a short while, I stopped caring because we had such a good time. At the end of the evening, he made an unusual request and asked for my address, then told me he was going to come round and say hello one day. Given the amount of alcohol consumed I thought it was pretty unlikely that he would remember…but I rather liked the novel and old-fashioned approach, and would have been more than happy for him to turn up at my door.

Two days later, a message from Mr Alien:
‘My friend has forgotten your address but asked me for your number, is that ok?’

I had no idea if Mr Alien had told any of his friends what had happened between us and this felt slightly awkward, but I took this as tacit approval that he was ok with it. And I had managed to find another Real Life Man!! A date with his friend was duly arranged via the gloriously old-fashioned method of actually speaking to each other on the phone. There was only one problem with this scenario in my mind. I knew we would get on well and have a laugh, and I was excited about it, but I was quite concerned that he seemed to be so much older than me. When I had imagined my ‘ideal’ man, I was aiming for about 2 years younger!

But hey, it was just going to be one date. A couple of drinks, a bit of a laugh…and then on with the new life plan. Besides, I persuaded myself that there could be some strategic advantages to dating an older man:

older man

  1. Great sex (should that be at number 1? Oh well, it is!)
  2. Knowing what they want, in life and from relationships – the benefit of accumulated life experience
  3. Stability – financial, work, housing
  4. The possibility of actual phone conversations, rather than text and whatsapp (what a novelty!)

And thus began a whirlwind. We had 3 dates in the first week, and on date 3 I started to really fall for him. Commit or Quit became irrelevant, because I knew it was a commit from date 2. This was…different. That very rare thing where someone just gets it, and gets you, without really needing to explain. Someone so similar and so familiar, but just different enough to make it interesting. I was almost correct in my age assumptions; and found out he was 18 years older than me. But I no longer cared at all.

There were three more dates in week two. By which time, we had revealed several skeletons in our closets, discussed possible marriage and living together, and had both completely freaked out at how this was all turning out. The life plan, so new and so shiny, suddenly seemed to require a hasty rewrite.

Then off he went on a long-planned holiday. Intended to be a break from the intensity and a bit of thinking time, I spent the first couple of days in slight shock that I appeared to be in an actual relationship with someone old enough to be my dad. And wondered if the reason why things seemed to be moving so fast was because as you get older, you are more certain of what you want. And he certainly ticked all of my “ideal man” boxes – somewhat to my surprise.

The day before he was due to fly home, I had just got home from work, changed into my oldest comfy jeans and got the hoover out. Oh, the glamour. Whilst happily hoovering and singing along to my favourite songs, there was a knock at the door…and there was he, my lovely older man, a day early. “I wanted to surprise you” certainly achieved the desired effect, and whilst I was still speechless with shock (and wishing I was wearing something slightly less tatty and had washed my hair less than 3 days ago) was hastily followed up with “and I couldn’t wait any longer”.

I am never going to win any prizes for being soppy or romantic, but this was honestly the loveliest thing to have happened to me in years…possibly ever (sad I know). And suddenly, I was facing the thing that seemed so very unlikely to happen at the start of this year – the genuinely scary possibility that this could actually turn out to be a committed and serious relationship. PANIC TIME!!

This became even more real when he asked what I was doing the next weekend, and mentioned those start-of-relationship words that strike fear into everyone’s heart (or maybe just mine) – “shall we go on a weekend away?” I had known him for less than 4 weeks, and felt like I was on a fast-track to something potentially really exciting – or possibly a whirlwind of total disaster. Having muttered a slightly reluctant yes, it was time to find out which it would be….and I will tell all next time, skeletons and all…


Where it all began: read Briony’s:Commit or Quit dating strategy



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