The pluses and minuses of having 50 dates in 2 weeks

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).

Positives

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.

3. Have a system to the dating process (which will help with any rejection).
This sounds really unromantic, but there is a numbers game involved. The reality is most people won’t match. Sometimes you know on the first date. Sometimes the second or the fifth. I didn’t find someone I really liked until the forty-eighth date (and I didn’t know until I dated them for 2 weeks). And I almost scared them away by putting drops of essential oils in his beer on the first date (to help him with the flu). Would have some earlier dates been a match if we went to a third or fifth? I’ll never know. But it didn’t matter as there was the next fish to catch.

4. End the date well.
Some strange things can happen on a date. For example:

• You got interrogated.
• One of you takes offence at something.
• You go for a drive and ending up at someone’s private vineyard more than two hours away (with the obvious expectation from them of something more on a first date).
• You find your date doesn’t remember your previous ‘chat’ because they actually had a virtual dating assistant who converses for them online.
• You get fed ‘hash cookies’ and end up having to be saved by a friend because you are hallucinating.
  Most men are well-intentioned (even if it seems a bit strange) but the ending shows respect but also allows you to cherish the moment. It allows you to open up for the next date without carrying any baggage over.

5. One can choose. Not just settle for someone because they are lonely.
It’s a “Hell yes!” Not a “Hell no!” If you don’t feel it early, you won’t ever feel it. You’ll just justify.
I know I seem to contradict myself a little as you might not know till some dates. But you know whether you ‘might’ feel it later. So you give yourself the chance. But there are some people who are ‘nice’ but somehow you know you won’t ever feel it with. And some people keep going and end up settling because it’s better than being alone. But for women, it is not difficult to get a date. So let’s just go on and see.

6. Don’t put them in the centre of your universe.
Men don’t like this. This is needy, clingy. Think about cats and dogs. Cats don’t need you, but if you’re they’ll take your affection. But they have their own priorities and life. You are not the centre of their universe. But they do love you too. Dogs pine every minute you aren’t there and make you feel guilty that you’ve neglected them. Many women are like this to men they are interested in. The man has his own priorities and jobs too. You are part of that, but not the only part. Don’t make them feel guilty you aren’t giving every bit of attention every minute of the day like a dog that wants a walk.

7. Assume they’re into you.
Do you ever create the negative by thinking negatively? The slight frown, hesitancy, words which reflect doubt and decrease your attractiveness. Assuming you are not attractive and they are not into you, will only make you less attractive and less likely to have good chemistry. Assume they are into you until proven otherwise. And then, give them a bit more of a chance. You never know. Men often need more time to open up and process. For women, it can seem like a sprint (to find a soul mate), for men it might be a marathon.

Negatives:

1. You will be disappointed.
But be selective about what is a red flag and not. Disappoints are not always – “no never’s”. But some red flags include:

•  Man-child. Anyone who can’t seem to get over 6-year-old dramas and behaviours and see everything as against them. By definition, this is a child. Not a man.
• He tells you upfront that “he doesn’t do relationships”, “I’m a loner” or “not looking to commit to anything”. You can’t change this man – even if you like him. Trust me, I’ve tried.
• Assume you’re not the only one they’re dating. This is a tricky one. Men and women get this wrong. Until there’s a conversation about being exclusive, assume you’re not the only one they’re seeing. Otherwise, you will not only be disappointed, but you might also be devastated.
• If you’re not their top priority, your appointments are a ‘maybe’. This is the same for girls and guys. It’s an indication of their interest. This can be difficult if you’re more into them than they are into you. But it gives you a guide.

2. Stalkers exist, even if they aren’t that scary.
You’ll get texts from people you’ve broken from, they’ll try to add you on Facebook, you’ll get people who really want to get together with you even if you don’t. For example, there was someone with whom I didn’t feel any chemistry with but he kept calling me. I blocked him. Facebook. Blocked him. Instagram messages. Flowers at your house. Some people don’t get it that you’re not into them. There aren’t really that many bad people out there and these types are actually mostly harmless, but don’t be afraid to be direct and block them if needs be.

Eventually, after all, the dating and numbering and ranking and carrying on have its saturation point, you will have to decide which suitor fits you best. Determining which is right. How will you decide?