30 Lessons I’ve Learned from My 30 Dates

I’ve never really been into self-help books, or spiritual journeys.  For me, the aim of 30 Dates was pretty fun – enjoy some nice simple dates, where I hadn’t invested anything into my ‘relationship’ with the guy beforehand.  Proper blind dates.  No expectations.

And yet, as the Challenge progressed, I found myself becoming an unwitting dating guru for my friends!  Not just date ideas, but friends came to me with queries about dating websites, singles events, and even what to message guys they’d met online!

Even some of my Dates would ask for advice – asking me where to take girls, and how to create successful online dating profiles … and who could forget my painful date tutoring ‘The Pupil’?!

And so, inspired by a question Cosmopolitan asked me very early on in this Challenge … here are the 30 Lessons I have learnt from my 30 Dates.

  1.  A first date doesn’t have to just be dinner or a drink – my best dates have been the more adventurous or unusual ones (The Enigma, The Fake Pimpernel, The Oxford Blue)
  2. Spontaneity has a Time and a Place – It’s one thing to go for an unplanned drink at the end of a date (The Enigma), but quite another to have no plan whatsoever, and end up eating at a random restaurant in the middle of nowhere (The Booby Prize)
  3. There are some amazing things to do in London – and there’s something new or different happening every night.  Look at Disappearing Dining (Queen’s Guard), and Dine Mile High (The Jet-Setter)
  4. Laughter can be the best ice breaker – two of my best dates started with humour – BUG at the BFI with The Superhero Alter-Ego, and (inadvertently!) the cringey Toilet Tour with The Fresh Prince.
  5. Burlesque is not a first date venue! – But if you’re already sleeping with the guy, by all means go for it! (The Burlesque Dancer)
  6. New York is a bloody exciting place to go on a date! (The New Yorker)
  7. Bullfighting is really brutal!  I said I wouldn’t judge it until I saw it …. The amphitheatre was beautiful, the bull-fighting seemed pretty unnecessary.  My favourite bit was when the bull got saved by a herd of cows … even if I did mishear the Argentine Matador and think he said clowns before they appeared!)
  8. The fine for climbing the Hollywood Sign is only $103 ….. is it bad that I think that’s probably worth it?! (The Hollywood Actor)
  9. Everyone loves a surprise – How often in life do you get real surprises?  Birthdays maybe?  If you’re lucky, you might have a partner who regularly treats you with surprises. But as a singleton, proper surprises are pretty few and far between.  So the surprise elements of the dates were amazing!  (The Challenger, The Fake Pimpernel, The Enigma, The Best Man, The Superhero Alter-Ego)
  10. You can have some really fun dates for free – (The Best Man, The Stallion)
  11. But if you do want to splurge, there are also some amazing restaurants to try in London! (The Enigma (Dates 1 and 2) and The Superhero Alter-Ego)
  12. Afternoon dates can be just as fun as evening ones(The One with The Sign, The Hollywood Actor, The Original Pimpernel, The Stallion)
  13. There are some really fun, cool single guys out there.  No one need panic about approaching thirty and being single!! Trust me, there are some really eligible guys out there who aren’t taken!  Even if some online dating sites and singles events might suggest otherwise!
  14. For the most part, you can trust your friends to spot a good date! Seriously, with a couple of notable exceptions, my friends did really well!  I’ve repeatedly admitted how picky I am, and yet looking back over my thirty dates, they really were an upstanding, eligible bunch!
  15. Going on a blind date with a friend’s brother is an automatic comfort zone – Both my dates with friends’ brothers – The Model Brother and The Big Kid – were really fun and banter-filled from the start, and I think knowing their sisters put me more at ease more quickly
  16. Speed Dating attracts men who never normally talk to women …. Or usually frequent bars!  If your ideal man is a member of the IT Crowd, fill your speed dating boots!
  17. Tinder is amazing!  An app which has managed to dodge the stigma of online dating, and attract nice normal guys who aren’t (all) just after a one night stand.
  18. If you’re going on a Blind Date, and you’re taller 5’6’’ or over, definitely wear flats!  Three of my dates were shorter than me – one by a good four inches!
  19.  Confidence is attractive – And not just in the guys.  Some guys were really affronted when they heard about my crazy challenge, but I’ve definite noticed the effect it’s had on a lot of hot single guys I know.  The more confident I’ve become thanks to this Challenge, the hotter the guys hitting on me! And by contrast …. a lack of confidence is really unattractive – something I noticed with The Pupil.
  20. Arrogance isn’t …. so if you’re confident, you also need to be able to laugh at yourself at the same time.  (The Exhibitionist)
  21. Enthusiasm is everything – As my date with Mr Twenty40 proved, being enthusiastic about what you’re doing (or not being enthusiastic) definitely affects how attractive you are to the opposite sex.
  22. GSOH is a must.  You need to share a common sense of humour … otherwise it can be really pretty awkward (some of my jokes on the date with The Exhibitionist were literally met with tumbleweed silence!).
  23. Make sure you know where you stand – Not everyone is an open book, but sometimes you need to know what the other person is looking for.  Don’t assume just because a guy is on a date, that he’s looking for a relationship!  (The Enigma)
  24. You can have a really fun date with someone you almost immediately mutually acknowledge no attraction to! (The One with the GSOH)
  25. You can have still have a really bad date with someone you thought you had a connection with! (my real date with The Skype Date)
  26. Sometimes He’s Just Not That Into You – it’s a harsh lesson to learn, but I’m definitely beginning to learn the virtue of Miss32’s dating experience.  Her mantra – if he’s interested, he’ll text you.  If he’s not, he won’t.  (Return of the Henley Boy – Part Three)
  27. That you can make anything happen – look how this crazy challenge developed in a few short weeks, from a simple Facebook idea, to an internationally-stretching adventure
  28. That I can write … and people want to read it!  That may sound a stupid thing to say, but the reaction to my blog has been really touching, particularly from readers who really aren’t my target audience.  It’s really cool to hear guys regularly reading the blog, and appreciating a humour, which is often just me talking how I would normally talk.  It’s a nice feeling to be completely honest, just talk how I normally talk, and have people appreciate it.  If anything that’s probably been more of a confidence boost than the dates!
  29. You should feel like he’s a prize.  You need to like him as much as he likes you – because no one likes to feel like they can ‘do better’.  And sometimes someone being too into you can be just as much of a turn off as them not trying at all. You should never feel like you’re having to settle!
  30. But you always need to treat yourself as the ultimate prize.  It’s something you always need to remember when you’re dating, and generally in relationships.  If you don’t love yourself, then how can someone else love you?  And if you have no self-respect, you’ll let guys walk all over you. (Return of the Henley Boy Part Three!)  And sometimes, no matter how eligible you are, you might end up on your own for a period of time, and you need to be happy and confident when you’re flying solo.

Miss Twenty-Nine xxx

2 Comments on 30 Lessons I’ve Learned from My 30 Dates

  1. PLEASE tell me you’ve got a publishing deal!
    I have a five year ole daughter and when she hits the right age I want to give it to her, with highlighted bits and annotated margins and a whole heap of love to respect her heart and her love as she wants it to be respected x

3 Trackbacks / Pingbacks

  1. The Second Date, The Enigma & The Eclipse | 30 Dates - The Experiments
  2. Experimental Dater Twenty-Three – The Enigma | 30 Dates - The Experiments
  3. Worth reading: 30 Lessons I’ve Learned from My 30 Dates « Five SSSSS

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