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The pluses and minuses of having 50 dates in 2 weeks


The pluses and minuses of having 50 dates in 2 weeks

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Inspire is delighted to have teamed up with Expat Life magazine to bring you more great content to do with Thailand

10 lessons learned from 50 dates (with 50 different people) in 2 weeks.

I’ve been engaged twice. But I hadn’t found the formula for true love. So I downloaded 5 dating apps and went on 50 dates in 2 weeks with many funny and sometimes scary incidences (including being given hash cookies and being limousine driven 2.5 hours to a private vineyard on a first date). Below are some of the lessons I learned and the stories behind them.

But first of all, you might ask, how did I do it? And why? It was 2013 when I broke off my 2nd engagement. I was freaked out because I didn’t know who I really was. After reading Eat Pray Love by Elizabeth Gilbert (who had done something similar to go on a spiritual quest), I decided to go to Thailand and ended up staying 5 years; starting a business, becoming a ambassador for Lorna Jane, having my products promoted by the Princess of Abu Dhabi and my business eventually sold to a private equity firm in Hong Kong for 7 figures.

So after a successful career and being single by choice, I returned to the dating game, I felt a bit more whole than I did when I broke off my engagement with my former doctor fiancé. Except I wasn’t. My friends were all ‘coupled’ and I found myself eating dinner by myself most nights. So I decided to do something about it. I downloaded 5 dating apps and went on a dating spree. This is what I learned in 10 lessons (5 positives and 5 negatives).


1. Everyone you date is a teacher
When you learn more about another, you learn more about yourself. Have you been ever criticised by your mother about something and then found that you did it on someone else? You don’t know that (and can’t correct for it) until actually have someone else to do it on. And not everyone will tell you. The quiet boyfriend might just put up with it until they can’t take anymore. But on the 48th date, I found someone who took me up on some of my ‘mother issues’ – i.e. doing what my mother did which I ended up doing on others. How many ‘potential husbands’ did I scare off because I was doing my mother?

On the other hand, I dated lawyers, investment bankers, English, Brazilian’s, Chilean’s, German’s, and even strippers and even writing this I feel a ‘stereotype’ of each in my head. But I found the stripper very business smart, people you expect to be boring were funny, some cultures shocking and some very spontaneous. It’s like living many lives in many countries – even it for a short time.

2. Being yourself is not always the right thing – on a first date.
One a first date with a German – I mentioned that I once had a gun put to my head (one of the later sagas involving my business life in South of Thailand). Being of a conservative type – it was a bit too much imagery to share for him. Not that it would bother too many people, but one should be able to read their date and not just blurt things out because you are naturally a ‘sharing’ person. Other times include sharing that you stayed at a friend’s house just to see what it’s like to live with a baby and being able to live out of one suitcase for 5 years to a high flying investment banker. At least be wary of what you share until they really get to know you. First date impressions count and you want to be able to decide if there should be a second date.


Source: Expat Life Thailand

Inspire is delighted to have teamed up with Expat Life magazine to bring you more great content to do with Thailand

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