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Dear Uncle Henry,

I am a slightly more mature gentleman. I have recently divorced after 20 years of marriage and I am now about to go out on the dating scene for the first time in over 2 decades. I am not sure where to start.

I wondered if you had any advice to get me on the path, as I would like to do it with a gentlemanly grace and panache, but I’m also a little nervous about stepping out into this world, it has been sometime.

Yours Faithfully,


California, USA


Dear Duncan,

Thank you for your question.

Your situation is a frequent occurrence in today’s society and when I was divorced in my late forties it was a challenge to ‘get back on the dating horse’. I commend you for asking for advice!

Recently I watched ‘Crazy, Stupid, Love’, a film that deals with a man whose wife has asked him for a divorce and he hits the ‘singles scene’ under the guidance of his new friend Jacob, an exceptionally slick bachelor. I would recommend you watch it as it is a good film, but I would not take it all to heart, though it does deal with some of the issues I am sure you are encountering. The main character, like you, will get through it and come out on top at the other end.

Self-confidence is the first hurdle to overcome. It is daunting to go out there and be judged, so let us help to build up that confidence.

Sometimes, self confidence is built from the outside in and I would assume the wardrobe and the waistline are not in robust health? So, lets start from the outside to build that confidence. I am not trying to turn you into a smooth six-packed man, just one who takes care of himself and is smart in appearance.

Either find a stylist in your area or pick a couple of good books and then hit a store with a personal shopper. Change and update your wardrobe, pick stylish items over fashionable items, as you want to suit your age and personal style.

Start exercising and eating well and healthy, once again, seek expert advice to help you on this path. It might take a little while to see the physical change, but the mental changes will appear much faster and I can assure you that the confidence will rise.

With the technology of today, it becomes much easier to get back on the dating scene. Online Dating is a perfect way to start, there are a number of websites on which you can put your profile, but I would go with one of  the long established ones to start with. There was a guest article written about it here.

If you need help with the profile, ask a trusted female friend to help you decipher what you want in a partner and what is the best side of you. It is generally easier to talk to women about these kind of things than our fellow men, though that is not always the case.

You can try your luck at Bars, and there are generally a number of ‘singles nights’, some are focused for targeted age groups. This is  where you can engage in conversation and keep building up that confidence. If you are a little trepidatious, you can find a friend to accompany you.

If you have hobby, go out and join a group that does your favourite hobby or hobbies. If you don’t have one, the time is now to go out and do that thing that you always wanted to learn.  It will get you out and about, it will make you meet people and give you something to talk about other than work!

As for the Dating itself, the young #1PG, wrote some excellent articles on dates here. Do take a look at those and the other Romantic Gentleman articles. If you were in London, I would suggest popping along to a PG course or two, but don’t worry, they will be in the USA soon.

Also, I am encouraging the Perfect Gentleman team to deal with Mature Gentleman issues in all aspects of their education and media outputs. I think they are listening, there will be articles on this in the future along with courses and elements in order to help you and others in a similar situation.

Good Luck, I hope this helps starting your journey and do stay in touch!

I am off to watch ‘Crazy Stupid Love’ again and raise a glass of whiskey in your honour!

Toddle Pip!


Uncle Henry


If you have a question for Uncle Henry email or #askhenry on Twitter @ThePGentlemen

We abbreviate questions and change the names/locations for privacy’s sake.

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