Oscars Top Five Dating Tips

Got your eyes on a lady or lad but low on luck? Try some of Oscar's patented dating tips - 70 per cent of the time, they work... every time

1. Your mail >>>> their letterbox

Classic. This works best if you share a letterbox/apartment complex with your intended (although it can still work if they live elsewhere – just blame the postal service). Simply take your mail and put it into their letterbox. If they return your mail to you personally, you have a great angle to work from. If they return it to the post office, it just means they’re playing hard to get.

2. Remembering their itinerary

There’s a fine line between stalker and romantically concerned but Oscar doesn’t waste time with semantics. Remember every bit of information your future lover gives you. Where do they get their coffee? What time do they get up in the morning? Why didn’t they answer your text at 8:39pm the previous night when you knew they were at home and weren’t watching their favourite TV show which finished at 8:30pm? All these questions can be answered by taking notes, writing reminders, and checking their phone when they leave it unlocked. It’s that simple!

Oscar: "I thought you were shooting a commercial in Madrid then a week in Turkey then back on the 21st, British Airways flight 117?” Nailed it.

3. Be a sweetie (or fake it ‘til you make it)

Whether it means throwing an impromptu surprise party for your annoying roommate, begrudgingly matchmaking for your friend, or pretending to be nice to children, impress your future date with magnanimous worldly kindness. It’s only for a little while. Only for a little while.

4. The Five Phases

After writing The Art of War, the ancient Chinese general and philosopher Sun Tzu wrote the similarly acclaimed but lesser-known Five Phases. Trust the Five Phases.

Phase One: Active Ignoring: You’ve seen them, but do not engage. Do not show interest in them. Ignore for at least 5 minutes.

Phase Two: Fake Friend Across the Room: This works best in a crowded room. Pretend you’ve seen an acquaintance and stride confidently across the room. It’ll make you seem confident, sociable and approachable. Get out of eyesight quickly after this.

Phase Three: Fake Phone Call: Sun Tzu originally envisioned this as ‘Fake Messenger Pigeon.’ As they inevitably approach you pretend to be on the phone, loudly being important, assertive and attractive. Oscar’s example: “I don’t care how much it costs! They’re orphans! Get them out of there!” Bang on the mark.

Phase Four: Invite to Drink: The integral phase. Whether you receive a drink or buy them a drink, this step must be observed.

Phase Five: Seal the Deal: This step involves some improvisation. Pull a dance move, recite a poem, play a jazz flute solo. This is the show of skill and/or charisma that will guarantee romance.

5. Be famous

It’s always helpful to be famous and/or successful. Oscar Madison is a well-known sports commentator and journalist and he gets dates like, all the time. 

And there you have it! Welcome to Date City, population: you.