• Admin
• September 03, 2023
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Our writer, Jerry O'Hare, humorously explores the age-old debate of whether attending dating events alone or with a wingman/woman is preferable.

Yes, it's true, I've frequented numerous dating events. As they say, you must go through many encounters before finding your prince or princess. I've dabbled in them all—speed dating, lock and key, quiz dating—you name it, I've been there, dressed to impress and armed with a clever turn of phrase.

Now, in my retirement, friends often seek my dating wisdom, and one question arises time and again: Should one brave the dating scene alone or bring along a trusty wingman? In my view, there's no simple answer; both options have their pros and cons, which I'll delve into below.

Let's start with the pros. Having backup is fantastic; it means you can arrive early, linger late, and avoid appearing like a lone wolf or, worse, a phone addict. In my experience, many of the opposite sex also arrive with friends, making conversation easier if you're accompanied.

A wingman also projects sociability, broadcasting, "Look at me, I have friends!" Plus, they can fill in conversational gaps and sing your praises, highlighting your many positive traits—ones you might be too modest to mention yourself.

Now, onto the cons. This one's rather obvious to me: having a buddy along can easily transform a purposeful evening into just another night out. It's easier to stay focused on why you bought that ticket in the first place when you attend solo.

Choosing your wingman carefully is paramount. You don't want someone too dissimilar to you in terms of looks, as they might end up overshadowing you or being a drag. Opt for an outgoing companion who won't cling to you all night, deterring potential suitors.

I've learned this through trial and error. I've woken up with a kebab as a pillow, with fuzzy memories of chatting endlessly with my friend while opportunities slipped by. I've been sidelined by the girl of my dreams as she chats up the 6'4" Adonis I convinced to tag along, and I've played nursemaid to a friend who preferred bending my ear to approaching any eligible bachelorettes.

So, what's my advice? If you can find a wingman who takes it seriously and matches you in looks and conversation, then by all means, wing it. If not, you're better off flying solo. But who am I to dictate? Just someone who went on over 30 dates before finding success. So, happy dating, and farewell!