QUESTION CAROLINE: She’s 40 years older… can we date?

If you have a problem please email Caroline at  Caroline reads all your letters but regrets not being able to answer them all personally

If you have a problem please email Caroline at  Caroline reads all your letters but regrets not being able to answer them all personally

If you have a problem, please email Caroline at: [email protected]. Caroline reads all your letters but regrets not being able to answer them all personally

She’s 40 years older… can we date?

Q I am a man in my early twenties living with my parents. Every week I drive them to a local cafe where they meet up with friends. Recently, I was parking the car when one of my parents’ friends stopped. The driver, a woman in her sixties, stopped her vehicle and as she got out, her skirt rode up her thighs to reveal amazing legs. Since then I can’t get her out of my mind. I did consider asking her out for a drink, but I’m too shy to do so. I also wonder what my parents would think if I was attracted to someone their own age.

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

I think, as you’ve probably guessed, your parents wouldn’t be happy if you were dating someone their age from their friendship group. The reality of a relationship—if you were hoping for that—with a woman 40 years her senior is that it would almost certainly be short-lived. You are in completely different stages of life and in the end there is little room for progress. However, I think it’s probably not this particular woman that you’re really attracted to, just her sexy legs and what they represent – a very natural desire for a girlfriend and a sexual relationship.

Since you still live with your parents and are shy, I’m guessing you haven’t had many relationships, or maybe none at all. That’s fine in many ways, of course, because life isn’t a race and there’s no shame in being a virgin in your twenties. Everyone has to go at their own pace and this can be a difficult age. But the lack of a girlfriend makes you unhappy.

Having sexual feelings that you want to explore but can’t due to lack of opportunity can lead to a real sense of loneliness. Especially if your peers are more successful with their love lives. You may be suffering from social anxiety. So consider counseling and support to find the confidence to make friends and ask girls out. Contact or, charities that support youth mental health. You can also join, a digital mental health platform that gives you access to an online community of colleagues and counselors.

I think it would really help to talk through all your feelings. You may be able to become more independent over time by leaving the parental home. But please forget this woman. She obviously has aroused sexual desire in you, but I think what you really need is a girlfriend closer to your own age.

I struggle with anxiety and OCD

Q I’m really having a hard time. I suffered from anxiety and obsessive compulsive disorder (OCD) when I was in my teens, but eventually learned to deal with it. I am now in my mid-30s. However, after almost two years of pandemic, I have anxiety problems again. I also find it difficult to sleep. My GP has referred me for Cognitive Behavioral Therapy (CBT), but there is a long waiting list and I cannot afford to go private. How can I cope? I’ve almost managed to suppress the OCD, but I feel nervous most of the time.

A I’m sorry you’re having such a hard time. Remember you learned how to deal with your fear before so you can do it again, but it sounds like you need a little refresher on what worked. Exercise and daylight are crucial, as is human connection.

So take daily walks (or swim or bike) and make time to see (or talk) close friends or your partner and confide in them. Kindness to yourself is also important, so don’t push too hard with a lot of “shoulds,” but take part in relaxing activities like taking a warm bath or reading a good book.

You can also try phone apps such as the Stress & Anxiety Companion, which is approved by the NHS (on the App Store or Google Play, from £1.99 per month) to coach you in CBT, and the free podcast Nothing Much Happens to help you sleep. Although you say you have your OCD under control, it can be a debilitating condition that often requires professional help and sometimes medication — which can also help with anxiety. So see your GP again if you feel out of control and check out the charity for support.

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