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Dating Skills for Maturing Men

I am sitting alone at a table for two in Galatea, the smartest of Glastonbury’s informal range of eating places.  Wearing smart casual gear which I hope looks youthful, I am waiting for my blind date, Jackie, to appear.  To look my best, I am not wearing my glasses, which means that people entering the room are blurs to me.  She looked good in the picture she sent me, but how long ago was that?  A rather bulky female blur comes in, and I half rise, then sit back in relief.  Now a slim and rather sexy female blur glides in, and I stand up.  I’ve got it right – it is Jackie.  As she gets closer, I realise she is wearing a gorgeous creamy, linen semi-transparent trouser suit, and a sense of elation runs right through me.

Some years before this scene, I recall one of the single guys in my men’s group telling me how he’d met a girl through a soulmates ad, and had a blind date with her.  It seemed scary and artificial to me, and I declared I’d never do it.  In fact in my 50s, I had numerous blind dates through soulmates ads, and found two good relationships through them.

If you’ve been many years in one relationship, it’s a strange new world to meet in mid-life.  This is one of the biggest re-inventions you may need to take on.  Ideally, before you plunge into dating, you need to sort yourself out more basically.  This means clearing self-destructive habits like depression, anger, addiction (see Chapter 7), and learning the skills of intimacy: see earlier in this Chapter.

Here are some guidelines to get you started:

      • Make the best of yourself.  If you’ve been living alone, or in a long-term relationship, you may be used to scruffiness.  If you’re dating, you will need smart, freshly washed clothes, a good shave and haircut, and fresh breath: this assumes you want to succeed, and are not hooked on being rejected….
      • Screen before you date.  Every blind date is a big emotional and time investment.  Do as much screening as you can before meeting up, to improve your chances of success.  Know the kind of partner you are looking for, and check things out by phone or email.  Understand what she wants, and if you’re likely to suit her.  Ask for a picture, and send yours.  Learn what matters most to you, and the questions that can explore this.
      • Enjoy the journey, not the outcome.  Blind dates are nerve-wracking: you are both accepting or rejecting each other, and it probably happens within the first minute.  I can recall a couple of blind dates with truly gorgeous women, who ticked all my boxes, but were clearly not interested.  There is a gift in all this, learning to value yourself even when she turns you down.  I tried to enjoy the conversations, even when they were going nowhere.
      • Blind dates are not therapy sessions.  If you’re still hurting from a major breakup, this nice woman across the table may seem ideal to pour out your troubles to.  Don’t!  Start with easy topics, go gradually deeper if it suits both of you.  Keep it a dialogue: ask plenty of questions, talk about yourself, but not for too long.  Talk about positives: what you enjoy, what you are looking for and offer in a relationship.
      • Value what you offer.  You may worry about your looks, but don’t be hard on yourself.  You are not in your twenties, that’s just a fact.  Fortunately, most mature women value other qualities more than looks.  If you have learned Intimacy 101, if you offer emotional competence, empathy and dependability, you are a good prospect!


This is an excerpt from Alan’s forthcoming book: if you would like to receive further excerpts and information about the book, sign up to this blog as a follower.