Ask Caroline: Dating an older woman and mental health struggles

Q. I am a man in his 20s and I live with my parents. Every week I take them to a local cafe, where they meet friends to 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, when she got out of it, her skirt rode up over her thighs to reveal incredible legs. Since then, I haven’t been able to get her out of my mind. I thought about asking her out for a drink, but I’m too shy to do it. I also wonder what my parents would think of me being attracted to someone their own age.

A. It’s probably best that you don’t ask her out because I’m afraid this wouldn’t have had the desired result. She could have been flattered and rejected, but she could easily have been embarrassed, and the awkwardness of the situation could have had a detrimental effect (for someone who is shy) on your self-esteem.

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

Since you still live with your parents and are shy, I guess you may not have had many relationships, or possibly none. That, of course, is fine in many ways, as life is not a race and there is 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 cannot due to lack of opportunity can lead to a real sense of loneliness. Particularly if your partners are having more success with their love lives. You may suffer from social anxiety. So consider counseling and support to find the confidence to make friends and ask girls out.

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Contact themix.org.uk or youngminds.org.uk, charities that support the mental health of young people. you could also join kooth.com which is a digital mental health platform that gives you access to an online community of peers and counselors. I think it would really help to talk about all your feelings. Perhaps, in time, moving out of your parents’ house will allow you to be more independent. But please forget about this woman. She has obviously aroused sexual desire in you, but I think what you really need is a girlfriend closer to your age.

“I’m fighting anxiety and OCD”

Q. I am really struggling. I used to suffer from anxiety and obsessive-compulsive disorder (OCD) when I was a teenager, but I finally learned how to deal with them. I am now in my mid-30s. However, after almost two years of the pandemic I am having anxiety problems again. I also have trouble sleeping. My GP referred me for Cognitive Behavioral Therapy (CBT) but there is a long waiting list and I cannot afford to go privately. How can I cope? I am about to calm down the OCD, but I feel restless most of the time.

R. I am very sorry that you are struggling. Remember that she learned how to handle her anxiety before so she can do it again, but it seems like she needs a refresher on what worked. Exercise and daylight are crucial, as is human connection. So go for a daily walk (or swim or bike ride) and take some time to see (or talk to) and confide in close friends or your partner. Kindness to yourself is also important, so don’t pressure yourself with too many ‘shoulds’; instead, engage in relaxing activities like taking a hot bath or reading a good book. You can also try phone apps like the Stress and Anxiety Companion which is approved by the NHS (on the App Store or Google Play, from £1.99 a month) to train you in CBT, and the free podcast not much happens to help you sleep.

Although he says he is getting his OCD under control, it can be a debilitating condition that often needs professional help and sometimes medication, which can also help relieve anxiety. So see your GP again if you start to feel out of control and check out the charity. ocduk.org for support.

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