The Serial Dater’s Toolbox

The bit you didn’t see too much during the 30 Dates Challenge was the logistics behind serial dating!! And I was doing it very honestly and publicly! God knows how people manage to multi-time their lovers!

But just in case reading the blog has tempted you to do the same (as a couple of readers have suggested over Twitter @30dates), you may need some or all of the following to cram 30 Dates into 3 months …

1) Lady Parts! – Sorry boys, sometimes girls can get more easily branded slutty than guys can.  But when it comes to going on multiple first dates, and then rating them, for some reason, it’s a lot better received if you’re female!  That may be really unfair, and by all means go for it (I’m sure a boy would get way more than three snogs out of their 30 Dates!), but beware the backlash!

And so with that in mind …. the next thing you need (unless you’re into lady dating, in which case, change each of the following boy references to girl ones …)

2) MEN!  Yes, I realise that seems obvious, but it’s harder than it may seem!  First you need ….

3) LOTS of back-up options.  I genuinely have no clue how many men I spoke to during the Challenge, and even partly-arranged dates with before they backed out.  At least three men got so far as arranging actual dates before cancelling, and who could forget The No Show, who allegedly texted me two days beforehand, but only actually told me he wasn’t coming five minutes before we were due to meet!  Then you need …

4) Thick Skin – Not only for when total strangers back out at the last minute, but also  because if you want 30 Dates recommended by friends, it will require a lot of nagging and chasing friends!

5) Sources of Dates – If you can’t rely on friends for blind dates, and you don’t want to have met your dates beforehand, your next option is the internet.  There are literally hundreds of dating websites out there these days … so far I had the most luck on the app Tinder, if all you’re looking for is fun guys up for a simple date.


6) A decent list of who people are!  So you remember their names, and who has recommended them!

7) A lot of date ideas – See DoingSomething, TimeOut and DesignMyNight, and obviously trawl my blog for a whole variety of options 🙂

8) A good diary.  Make sure you know who you’re meeting, and when.  Especially if you’re planning on going on more than one date in a day -my closest dates were 15 minutes apart!

9) Google Maps – I got lost A LOT finding date locations

10) The Tube Planner app – If you’re in London

11) The Trainline app – If you’re outside London

12) A good phone battery – for all those apps!  I wouldn’t recommend an iPhone5 – mine died before I got home on most of the dates!

13) A phone with a good camera – I had an amazing summer and am so glad it’s recorded in hundreds of photos on my phone.  And you never know when you’re gonna spot a random celebrity at your date!


14) A Railcard – I didn’t have one of these, but wish I was still young enough to own one (for numerous reasons!)  But seriously, travel costs can mount up, so it’s always worth researching the cheapest deals, and whether booking in advance makes things cheaper.  At one point I was planning on meeting The Best Man in Liverpool, until I realised the train fare would cost me £90 for the day!

15) Free Parking – I think one of the reasons I was so sensible on my dates (and only snogged three of them!) was because on most of the dates, I had to collect my car at the end of the night.  Which meant my blaggy free parking in the centre of Reading came in very handy!

16) A Reliable Taxi Firm – For those dates when you have more than one drink!  Though at this point, I should highlight that Addison Lee massively messed me around after my date with The Superhero Alter-Ego, and I actually realised after the date that they charged my credit card for two taxis.  I’ve spent the last three weeks trying to complain – to no avail!  So would definitely recommend against using their phone app.  It seems really simple, but because it had my credit card details on file, the cab didn’t show, and yet I was charged for it – so I waited 2 hours to pay double the price!

17) A good friend, who knows where you are at all times (She says, sensibly, whilst persuading lots of people to go on multiple dates!)

18) A big smile.  Even if you don’t fancy someone, there’s no point being miserable.  And they say making yourself smile actually tricks your body into believing you’re enjoying yourself!

Date 16.4

19) Patience – some of the dates (and a LOT of the speed dates) were really pretty boring.  The Pupil took a LOT of effort, but by sticking it out, I managed to turn it around from just another dull night with a guy I didn’t fancy in the slightest, to something a bit different and worthwhile.  I’ve been speed-dating when other girls have stormed out of the bar, after seeing the ‘offerings’, and even watched on as one girl raised her date card above her head, and demonstratively ripped it into shreds!

20) Some stiff British Upper-Lip! – I really had to bite my tongue on the Tube with Mr Twenty40 (and did actually give him an earful about it once we’d got to the restaurant).

21) Flat shoes! – If you don’t know anything about the guy you’re meeting, I would definitely opt for flats (unless you’re shorter than everyone you’ve ever met!)  Also, if you don’t know what you’re going to be doing on the date, you may as well where something functional.  Some of the dates involved a great deal of walking.

22) More than one ‘polkadot dress’! – Otherwise everyone will think you only have one outfit!

23) An open mind. – The thing about blind dates, is the guy could turn out to be anyone.  I had dates with bankers, bar-tenders, professional yachtsman, army officers and sports agents.  And with guys with really different religious beliefs.  If you’re just going on first dates, you don’t have to marry the guy, so just make the most of each date, and don’t worry too much about the parts that aren’t perfect.

24) A good sense of humour – Because dates are a lot more fun if you’re laughing.  (One of the reasons my dates with The One with the GSOH, The Fresh Prince, and The Superhero Alter-Ego were all so much fun)

25) A LOT of different stories – otherwise you’ll begin to bore yourself repeating the same anecdotes.  As I learned at Shhh Dating … let your date take the lead, and that way you don’t know where the conversation will go!

26) A ‘system’ – I’ve touched on it before.  To keep track of who everyone was, who had referred him, and  when and where I was meeting him, I had various systems of file note and calendars, and even a special way to save the date’s phone number on my phone at different stages in the process (and depending on whether or not I’m hoping for a second date!)


27) Stamina – As you may have noticed from my later blogposts – I was genuinely shattered!  Most of my dates were at least 4 hours long, and when you factor in another 4 hours of travel, dating almost became a part-time job, on top of my normal life.  It was definitely a marathon, rather than a sprint, and I had to pace myself – if I had too many consecutive nights in London, either on dates or at singles events, I struggled to get up for work the next day.  In fact, much like a marathon, I barely remember most of the final third of the Dating Challenge – it seemed to whizz by!

28) An understanding boss!  I was moved to evening shift work when I returned from Madrid, which left 14 dates to go, and technically no weekday evenings.  My boss was fantastic – everyday I had a date scheduled, he let me work 9-5 instead of the 2-10 shift I was meant to be working.  (And I found out today he’s even been following the blog! So thank you!!)

29) Cash – Not just because serial dating can be really expensive!  You have to always be willing to pay!  You can’t go on dates expecting a free ride all the time.  Don’t get me wrong, it\s great to be treated – but as a friend suggested early in the Challenge, I didn’t start 30 Dates by 30 just to have a cheap summer.  I promised myself I would never let the guy pay for me if I didn’t enjoy the date, as I didn’t want to give him the wrong idea.  However not everyone thinks that way – I noticed this report in the Metro on the way to one of my dates!

30) Condoms – That’s not me admitting to any revelations …. I promise I was very honest the outcomes of all the dates, and I was a very good / boring girl!  But you should always be prepared … and safe!  (Good, responsible blog writer!)  And according to one of my colleagues … there’s always the ’30 Dicks in 30 Days’ Challenge … which I’m obviously NOT endorsing! 😉

Miss Twenty-Nine xxx

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