How to date a woman hotter than you

Ensure you don't get knocked out when punching above your weight

It is a practice variously described, but perhaps most commonly known as ‘punching above your weight’.

And, whilst you may think using a hand-to-hand combat analogy to describe dating to be a little overwrought, it actually sums up your situation better than you know.

Overreaching in the arena of dating is fraught with hardship and hindrances. Your mismatched partner may get people talking, pulses racing and buoy you with a never before-felt smugness, but the reality isn’t as romantic – less ‘a dozen roses’ and more ‘a dozen rounds’.

True, you may feel pretty special when the bell first rings on your relationship and, if you’re lucky, you’ll even see your fair share of satin robes falling to the ground as well. But, once you’ve endured several rounds of romance, the gloves’ll come off, you’ll start sweating over the smallest of things and – as is only to be expected when getting into the ring with a hard-hitting, stone-cold stunner – you’ll be inevitably and spectacularly knocked out.

But don’t throw in the towel just yet. Despite having the odds stacked royally against you, you can still roll with the punches. And, although there’s no definite rulebook for punching above your weight, we’re still firmly in your corner to help you the best we can.

Making your move in a club or bar may seem like an appealing idea – thanks largely to the social supercharger that is alcohol. But, rather than hitting the town in search of a prospective partner, try approaching women in a calmer, more considered environment.

Making your first impression at an art gallery, evening class or book club will help showcase your personality and, whereas propping up the bar with nothing but your lacklustre looks is unlikely to attract much attention, releasing your natural charisma and character is a much safer bet.

The key to maintaining a long-term relationship, especially with somebody who is clearly out of your league looks-wise, is to become friends with them first. Be very careful, however, not to fall into the ‘friendzone’ – a black hole of platonic despair and despondency into which beautiful women banish countless men.

Instead, split your time between friendship and flirting. Keep her on her toes, remind her that attraction is a two-way street, and don’t immediately lay your soul bare by throwing yourself at her feet.

Believe it or not, we all like a challenge – even solid tens. So, by befriending her and reminding her that there’s more to life than looks, you might actually open her eyes to a wider pool of possibility.

When you’ve become sufficiently comfortable with one another – but before the nature of your relationship is too definable – swoop in with ‘the charm’.

A complicated concept, ‘the charm’ eludes many men. But, statistically, if you’ve had to get by on something other than rakish good looks or a gym-built body all your life, you’re likely to have at least a cursory understanding of good old-fashioned romance. So, go ahead and sweep her off her feet.

Buy her dinner, bring her flowers and really listen to her when she talks. Have conversations that don’t involve how much you can bench press, and take an interest in her pursuits and hobbies – however mundane you may find them.

And flatter her. But remember, the art of flattery is not easily mastered. There are so many potential pitfalls waiting to trip you up that the practice could almost demand a section all for itself. In fact…

Compliments and cajolery are tricky to get right at the best of times. With a balance to be struck between indifference and creepiness, you must take frequency, sincerity and quality into account. And, when dating someone hotter than you are, the difficulties are taken to a whole new level.

If you compliment her too much – and without reciprocation – her ego will steadily grow until she looks at you one day and asks herself ‘I never feel as taken aback by his looks as he clearly does by mine. Could I do better?’

But, conversely, if you avoid sycophancy all together, there will come a time when another man – who may be better or worse looking than you are – comments on her hair or dress sense and wins her heart through the simplest of ways: attention.

The sheer number of problems and rules set out here probably make the idea of dating someone hotter than you terrifying. And yes, whilst at this point you probably think it’d be safer courting a pint or two of nitroglycerin, you shouldn’t actually worry.

For even though we began this discussion by likening relationships to literally being beaten up, the reality is that if someone is making you work for it because they think they’re hotter, forget them.

Never assume that you’re less attractive than someone, and never rule out approaching someone – whoever or wherever it may be – out of fear that you’re not good enough. Some of the best personalities can be found in those with less-than-brilliant looks and, conversely, some of the most attractive amongst us are about as charismatic as wet flannel.

So the only real piece of advice you need in order to date someone hotter than you is that there is no-one hotter than you. Confidence is key, gents, nothing is more attractive than someone who knows, and is comfortable with, who they are, and no-one is you-er than you.

So throw your hat in the ring, make sure you beat all those other contenders to the punch, and always remember, you’re a knockout in your own right.

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