I’m divorced 12 years and feel ridiculous chatting up women

I’m wary of internet dating and feel like a sad case chatting up women in pubs

PROBLEM: I am a 59-year-old divorced man and have joint custody of our 17-year-old daughter. I was heartbroken when the separation happened and always felt we could have resolved our issues, which were relatively minor compared to the difficulties that I know other couples have.

After the separation, I became very busy with work and completed both a degree and a masters programme. I also spent a lot of time with my daughter and remained close friends with my former wife. However, my life is changing very fast and I feel that I am losing control over my future. In the past year I appointed a manager to my firm, which has proven to be a good business move. My daughter has been successful in getting a scholarship to a very good university in the United States and I am very excited and proud of her. My ex-wife has also started dating someone for the first time since the break-up 12 years ago. I am suddenly feeling very lonely and have accepted that I should try and meet someone to fill the void.

I have considered internet dating, but I don’t see how chemistry and romance can develop in swiping left and right. Married friends have suggested setting me up with single women, but this just makes me feel like a charity case.

I have tried chatting up some women in local pubs, but afterwards I always feel ridiculous, and imagine that I must come across as a sad case.


ADVICE: All the answers to your quest for exploring someone in your life are in your letter: internet dating, asking friends to organise possible meet-ups with interesting women and chatting up people in bars. These are all the ways in which we might step out of our comfort zones and take the risk of exposing our interest in meeting a possible partner. That you have been separated for 12 years and not had a relationship does demonstrate how big a step this is for you, but, finally in your life, all the busyness has settled and now there are no excuses left and dating is facing you directly.

All relationships require risk. There is no way of having a relationship without vulnerability and exposure – you have to allow the other person into your life and under your skin and so this gives them the knowledge and ability to hurt you. The quality we need to develop in order to have this capacity for risk is courage (with intelligence) so that we can firstly, understand that we fear being hurt and secondly, have the ability to overcome this fear. This can be exaggerated by our past experiences of perhaps choosing badly in love and being rejected, humiliated and even derided.

If we let these experiences determine all our future relationships, we will only partake of short, safe and ultimately non-relationships such as one-night stands or largely text/email relationships. Fear has to be overcome and our defences let down to have a satisfactory, real and enduring relationship. If we are motivated to overcome fear in this area of our lives, it will also enhance our capacity in other areas. Imagine feeling free to express yourself openly and truthfully rather than defensively or obliquely in order to protect yourself from hurt? Of course, this has to be done with intelligence and good judgement but fear will always cloud this ability so the first task is to practice fearlessness.

Overcoming your fear of coming across as needy with your friends means that you ask and accept all offers of setting you up – your friends probably have a very good idea of what might suit you in a partner so swallow your embarrassment and say yes. As it is years since your last relationship, you will need to give yourself lots of experiences that will enhance your capacity to choose what will ultimately be a long-term partner, so internet dating is also on the cards.

Your prejudice against this is understandable but internet dating has now become the norm (even for people in their 40s, 50s and 60s) in terms of creating relationships and it will offer you choices beyond your location or friendship circle. Ask a friend, or your daughter, to help you set up a profile and suspend cynicism while you learn how to use this new dating medium.

The aim is to have fun and take risks that might widen your experience and expand your life – this is worth getting a little embarrassed for!

Lastly, the problem about chatting to women in pubs is the negative thinking you do afterwards. You are not a sad case, in fact you have had a very successful and fulfilling life – the problem is the critical rumination following any encounter where you risk judgement.

Do not let this fear and negative commentary stop you from finding someone to share your life with – be open and courageous and the world will respond with lots of possible romantic encounters for you.