Caroline West-Meads: ‘She’s 40 years older… can we date?’

ask caroline

Q. I am a man in my early 20s and live with my parents. Every week I drive them to a local café, where they meet friends for a catch-up. Recently, I was parking the car when one of my parents’ friends pulled up. The driver, a woman in her 60s, stopped her vehicle and as she got out her skirt rode up over her thighs to reveal amazing legs. Since then, I have been unable to get her out of my mind. I did think of asking her out for a drink, but I am too shy to do this. I also wonder what my parents would make of me being attracted to someone of their own age.

A. It is probably just as well that you didn’t ask her out because I fear this would not have had the desired outcome. She might have been flattered and declined, but she could easily have been embarrassed – and the awkwardness of the situation might have had a detrimental effect (for someone who’s shy) on your self-esteem.

I think your parents, as you’ve probably guessed, would not be happy with you dating someone their age from their friendship group. The reality of a relationship – if that is what you were hoping for – with a woman 40 years older is that it would almost certainly be short-lived. You are at totally different life stages and ultimately there is little room for it to progress. However, I think it is probably not this specific woman to whom you are really attracted, just her sexy legs and what they represent – a very natural longing for a girlfriend and a sexual relationship.

As you are still living with your parents and are shy, I am guessing that you may not have had many relationships, or possibly any. That is, of course, fine in many ways as life is not a race and there’s no shame in being a virgin in your 20s. Everyone must go at their own pace and this can be a difficult age. But the lack of a girlfriend is making you unhappy. Having sexual feelings that you want to explore but can’t through lack of opportunity can lead to a real sense of loneliness. Particularly if your peers are having more success with their love lives. You may be suffering from social anxiety. So consider counselling and support in order to find the confidence to make friends and ask girls out.

Contact or, charities which support mental health for young people. You could also join which is a digital mental health platform that gives you access to an online community of peers and counsellors. I think it would really help to talk all your feelings through. Perhaps in time, moving out of your parents’ home will enable you to become more independent. But please forget about this woman. She has obviously awakened sexual desire in you, but I think that what you really need is a girlfriend nearer your own age.

‘I’m struggling with anxiety and OCD’

Q. I am really struggling. I used to suffer from anxiety and obsessive compulsive disorder (OCD) when I was in my teens, but eventually learnt to manage them. I am now in my mid 30s. However, after nearly two years of pandemic I am having anxiety problems again. I’m also finding it difficult to sleep. My GP has referred me for cognitive behavioural therapy (CBT), but there is a long waiting list and I can’t afford to go privately. How can I cope? I’m just about managing to quell the OCD but I feel fidgety most of the time.

A. I’m so sorry that you are struggling. Remember that you learned to manage your anxiety before so you can do so again, but it sounds as if you need a bit of a refresher on what worked. Exercise and daylight are crucial, as well as human connection. So take daily walks (or swims or cycles) and make time to see (or talk to) and confide in close friends or your partner. Kindness to yourself is also important, so don’t pile on the pressure with lots of ‘shoulds’ – instead, engage in relaxing activities such as taking a hot bath or reading a good book. You could also try phone apps such as the Stress & Anxiety Companion which is NHS approved (on the App Store or Google Play, from £1.99 a month) to coach you in CBT, and the free podcast Nothing Much Happens to help you sleep.

Although you say you’re managing your OCD, it can be a debilitating condition that often needs professional help and sometimes medication – which may also help anxiety. So see your GP again if you start to feel out of control and check out the charity for support.

Find more of Caroline’s advice here