I'm having a late-sixties sexcapade - but am I leading my lover on?

With advice from Tess of the D'urbervilles

Tess: another victim of sexual double standards

I ran into my Heathcliff, a hunk I had casual sex with in my early thirties. It was a joy to reconnect - but after a few months (of unbridled and exquisite sex) I realised that he is quite boring. I am much more Thrushcross Grange than he: sometimes he plays with his PHONE (don't think like that) in PUBLIC, which is nothing but embarrassing. (We're English so embarrassed is our default position). I feel it is unfair of me to toy with him - I should let him go.

BUT

He's a birthday coming up (I've always had a thing for Leos). I am thinking of arranging a mini break - a surprise: a sensual romantic get-away. (We're in our late sixties ... who knew sex could be better when it's nearly too late than it was when it was just a bit too soon?) My internal Catherine is actually feeling a bit guilty - a bit of a user ... but is that just because I am not a man? Can old women get away with behaving like young men? RSVP ASAP ... no time to lose!

I am RSVPing extremely ASAP by bumping your message right to the top of my inbox - sorry, other letter-writers, but needs must for a woman in crisis. And as Leo season has only just begun, I hope this gets to you on time.

Your letter was a joy to receive: firstly because it is so well-written (would you like to come work for this publication? No perks and no salary but lots of fun), but also because it’s delicious that you are having a late-sixties liaison, AND that you assure me the loving is better than ever. So much to look forward to! So much to be embraced!

Given the joie de vivre your situation inspires, I’m desperate to tell you to throw caution to the wind and indulge in your romantic get-away without further soul-searching. But. I’m not sure I can.

Let’s start by working out exactly what it is you feel guilty about. Is it hooking up with someone you find a bit boring? I think that’s okay, so long as they know it’s casual, and you still treat them with respect. Is it having sex with someone you don’t see a future with? Again, I think that’s fine, and I’m going to assume you know it is, because you did exactly that with this very same man in your thirties. So, reading between the lines, I’m guessing a part of you suspects he wants more this time round, and you’re wondering whether it’s okay to pretend not to notice so you can continue to have fun.

It pains me to say it, but I think it’s best to be honest. If I’d been dating someone for three months and then they took me away for a romantic birthday mini-break, I’d assume we were heading in a relationship direction. So my advice to you is: don’t veto the trip idea, but see if you can have a conversation prior to proposing it, that establishes a fun, no-strings-attached kind of tone. If you can pull this off, the trip will be more fun for you too: you can revel in it without worrying all the time that you’re leading him on.

Because nothing is a greater barrier to intimacy (and good sex) than a guilty conscience; a truth heartbreakingly illustrated in Thomas Hardy’s Tess of the D’urbervilles. You might think this is a strange comparison, but I think Tess’ story speaks to your own in a number of ways. Tess, a sixteen year old living in 1870s Wessex, has a darker secret than you do: she loses her virginity outside of wedlock to an older man called Alec D’urberville, in an encounter Tess later describes as ‘confused surrender’. When she then meets the love of her life, Angel Clare, guilt about her sexual history threatens to divide them. Tess’ anxiety about the truth she is concealing haunts her; so much so that Angel’s marriage proposal draws forth horror: ‘She could hardly see, her eyes having filled with two blurring tears drawn forth by a grief which, to this her best friend and dear advocate, she could never explain.’ Tess avoids Angel, she grows sick, she desperately wants to come clean - and it is only when Angel himself admits, on their wedding night, that he has also slept with someone else before that Tess finally feels joy again, at the prospect of safely revealing her comparable history.