Cindy Gallop - Toyboy Warehouse Ambassador

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Cindy | Toyboy Warehouse Ambassador

Founder of IfWeRanTheWorld and winner of Advertising Woman of the Year, New York based Cindy uses Toyboy Warehouse to meet younger men from the UK. Through the community Cindy finds the casual relationships she prefers with men described as ‘extremely high caliber’. She’s now making improving perceptions of love and sex her business with MakeLoveNotPorn.

It all began eight years ago when Cindy was at a friend’s 40th birthday party in a villa in Ibiza…

“My friend Lucy came up to me on the dancefloor and said, ‘Cindy, you have to meet this woman here – she dates younger men too!’ Lucy dragged me over to a very nice Englishwoman, we were chatting and I asked her, ‘So how did you meet your younger man?’

“She replied, ‘Oh, I met him on’

“I fell on the floor in hysterics going, ‘That is the best url ever!’

“As soon as I got home to New York, I went to the site and thought, This is fantastic – so much better than the US cougar sites I’ve been using. I fired off an email to [email protected], saying, I absolutely love your site, this would be so welcome in the US, congratulations.

“Five minutes later I got an email back from the founder, Julia Macmillan, we became friends, and the rest is history. :)”


Cindy on Toyboy Dating: 

Toyboy dating means to me, very simply, doing what makes you happy.

“I’ve never wanted to be married. I’ve never wanted children. I don’t want a conventional relationship. I’m very open publicly about the fact that I date younger men casually and recreationally, because I believe that everyone should be free to design the relationship model that works for them (which may vary at different stages of your life), as opposed to the very limited number of relationship models society tells us it’s OK for us to engage in.

“Both women and men need more role models for the fact that you can live your life in a different way to what society dictates, and still be extremely happy.”


Cindy on her best Toyboy Warehouse experiences: 

“Honestly, way too many to detail. While I date younger men casually, I have one fundamental criterion, no matter how casual the relationship: they have to be a very, very nice person. I have terrific radar for very, very nice people. I have met a number of absolutely lovely younger men through TBW, and we date therefore in a context of mutual trust, respect, affection and liking. I’m only in London periodically, on business, but I’ve dated younger men through TBW over periods of a number of years – because of my criteria, my so-called ‘casual’ relationships often last a lot longer than other people’s so-called ‘committed’ ones.

“The younger men I date may go on to date girls their own age, but we stay friends and continue to meet up platonically, because I’m very fond of them and enjoy their company. I appreciate TBW for the fact that my dates through the site have generally been of extremely high caliber – nice, intelligent, good mannered (my dealbreaker, incidentally), and in some cases extraordinarily good-looking with amazing bodies (not obligatory, it’s more important to me that you’re nice than that you’re good-looking, but it doesn’t hurt!)”


Advice Cindy has for women considering dating younger men: 

1. Know that they really do think you’re beautiful (and relax and enjoy it).

Our society places such a premium on female youth and conventional attractiveness, older women can lose sight of how attractive they are in their maturity, and how much younger men who are into older women really do appreciate and admire that. I’m 55, and I’ve never been told I’m beautiful as often as I have been over the past ten years.

2. Tell them they’re beautiful, and how much you appreciate them.

Another mistake our society makes is to perpetuate the belief that compliments should be only one way, from men to women. I make a point of telling the younger men I date how beautiful they are, because that’s not a word we often apply to men, and it should be – and it’s clear when I do that, that they’ve never heard that before. One (extremely attractive) 21-year-old said to me shyly when I was complimenting him, ‘You make me feel sexy.’He’s sexy as hell, but he obviously hadn’t been hearing that from the girls his own age he was dating.

3. Fact of life: younger men are flaky.

At a practical level, while I would like this to be different as much as the next woman, younger men can be a lot more casual about arrangements, turning up and cancellations within acceptable time periods, in the way many younger people are generally. You should expect this and not get too upset about it, while at the same time making it clear what is and isn’t acceptable to you.

It’s worth bearing in mind that (as with all online dating) there will always be things going on in the other person’s life that you aren’t aware of. I’m a big believer in sexual etiquette; when you’ve had a fun night with someone, whether or not you intend to see them again, a brief text or email just to say thank you is always appropriate. I can tell you that some of my TBW dates who have not done this have had an email from me pointing out that one of the advantages of dating an older woman is the opportunity to shortcut some of life’s lessons, particularly where good manners are concerned – and I’ve received profuse apologies either immediately or, in some cases, some months later, explaining the circumstances (eg post-girlfriend breakup emotional upset, etc).


More about Cindy:

Cindy Gallop is a graduate of Somerville College, Oxford, whose background is brandbuilding, marketing and advertising – she started up the US office of ad agency Bartle Bogle Hegarty in New York in 1998 and in 2003 was named Advertising Woman of the Year.  She is the founder and CEO of; and of, launched at TED 2009. She and cofounders Corey Innis (CTO) and Oonie Chase (User Experience) launched in public beta in 2013.

She acts as board advisor to a number of tech ventures and consults on brand and business innovation for companies around the world, describing her consultancy approach as ‘I like to blow shit up. I am the Michael Bay of business.’ BusinessInsider last year named her one of 15 Most Important Marketing Strategy Thinkers Today, alongside Malcolm Gladwell and Seth Godin, and recently cited her as both number 33 on their list of 100 Most Influential Tech Women On Twitter, and number one on their list of Top 30 People In Advertising To Follow On Twitter. She published ‘Make Love Not Porn: Technology’s Hardcore Impact on Human Behavior’ as one of TED’s line of TEDBooks.

You can follow her on Twitter @CindyGallop