THE ORIGINAL DAILY - OUR BLOG : Winging it… Attending dating events solo or with a friend? THE ORIGINAL DAILY - OUR BLOG : Winging it… Attending dating events solo or with a friend?

Winging it… Attending dating events solo or with a friend?

Thursday February 27, 2020

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Our writer, Jerry O'hare takes a wry look at the age old question of whether or not dating events are best attended alone or with a wingman/woman. 


It’s true, I’ve been to a lot of dating events, but as they say you must kiss a lot of frogs before you find your prince or princess. I’ve tried them all, speed dating, lock and key, quiz dating…you name it, I’ve been there dressed to the nines and armed with a nicely fashioned turn of phrase.

Now that I’ve retired, friends come to me for dating advice and there’s one question I hear time and again. Should I date solo or should I bring a wingman? To my mind there isn’t a simple answer, there are pros and cons on both sides on which I’ll look to elaborate below.

So, first the pros. Having backup is great, it means you can turn up early, stay late and not look like Nobby no mates or even worse a phone junkie.  In my experience many of the opposite sex also turn up with their friends and it’s easier to speak if you’re accompanied.

Having a wingman also has the effect of making you look sociable, it’s shouting out ‘look at me, look at me! I have friends,’ and your friend can fill in the blanks if conversation stops flowing. Your friend can also big you up, talking about your many positive features, which of course you’ll be too modest to bring up yourself.

Now the cons. Well to me this is obvious, having a mate there can turn a night that was planned with purpose into just another might on the beers. It is easier to remain focused on why you bought a ticket in the first place if you attend said speed dating, book dating, yodel dating etc. on your own.

You must choose your wingman with care, you don’t want him too different from your score in terms of looks as either he’ll end leaving you behind or being a drag. Also, you need someone who’s outgoing and not going hang around you all night like a bad smell, deterring any potential suitors.

I know this as I’ve made all the mistakes. I’ve woken up the next morning with a kebab for a pillow, with hazy memories of a long chat with my mate whilst some sort of party was going on. I’ve been side lined by that night’s girl of my dreams while she’s chatting to the 6’4 Adonis I mistakenly convinced to come along with me, and I’ve had to nursemaid the friend who’s rather bend my ear than actually approach a living breathing female.

So, what’s my advice? If you can get a wingman who’ll take it seriously and is in your league in looks and chat, then I think it’s better to wing than solo. If not you’re better off relying on yourself. However, who I am to tell you what to do…well just someone who went dating over 30 times before it worked, so toodles and happy dating.