Shipwreck’s Guide to Understanding Men

A reader from Sydney recently emailed me asking for some first date tips, so Shipwreck has put himself to work to come up with some creative, original ideas that answer your questions of:

• questions to ask on a first date
• what to wear on a first date
• first date ideas
• first date sex

Let’s set the scene a bit first…

You’ve met a guy that you’re interested in, he’s worked his magic and you somehow agreed to a first date. Normally you’re a skeptic and think that most guys are %#&?heads, so you think “I wonder what makes this guy so special”, knowing full well that he’s probably just trying to get in your pants. That’s what the devil side of your head is telling you…

Meanwhile on the angel side, you’re thinking “Oh my god I can’t believe he chose me…what am I going to wear?…what questions should I ask him?…what should we do?” etc. etc. You get the picture.

Now before you stress yourself to bits, remember, the guy is probably just as nervous as you are.

So to put your nerves aside and enjoy the perfect first date, here’s some words of wisdom from Shipwreck -

Questions to Ask on a First Date

First date conversation sets the scene for what your date can expect of you. Don’t lie to them, make yourself out to be better than you really are, or undersell yourself. Your few hours together is an opportunity for you to say - “This is me…you’re either interested or you’re not”. If the guy is hotter than Brad Pitt and you just want to score, then lying may get you somewhere, but will more than likely hurt you down the track.Here are some great first date questions to ask your date:

1. “Do you read Shipwreck’s blog?” - yes, seriously! - if he doesn’t, you’ll know he’s probably a bit behind the eight ball when it comes to relationships, so don’t set your hopes too high
2. “Tell me about your ex’s - what do you honestly think went wrong?” - the way he answers this questions will tell you immediately what kind of person he is and how he treats relationships
3. “Have you ever considered turning gay?” - watch him squirm and make out that females are the best thing since life spread!
4. “What would you do if I fell pregnant?” - watch him squirm some more, but at least you’ll know his reaction and can decide whether to continue the conversation!
5. “How important is your car and your mates?” - this question could see him talking for the next 24hrs straight, telling you all about his car and funny stories about his mates. Use this one if you think the poor guy is nervous and needs to open up a bit.

What to Wear on a First Date

Choosing what to wear on a first date should be based around what you are comfortable in. If you look comfortable, he will feel more comfortable around you.

• Wear a dress - if you’re after a decent guy, dress to impress
• I’d say no to jeans…it depends on what you’re doing for the date, but where possible avoid them.
• Look as feminine as possible (check out my previous post on 3 things men can’t resist).
• Guys do notice hair…keep it simple but enticing
• Don’t go overboard on make-up…personally i’m not a fan of make-up…guys want to see who they’re actually going out with, and excessive make-up can look trashy (and can make you look much older than you really are)
• Make sure your handbag isn’t too big - you’re not going camping…keep it smallish…guys notice this (Shipwreck does anyway)

First Date Ideas
Shipwreck has a good friend whose idea of the perfect date is going to the pub, placing a bet on the horses and getting plastered together - yeah, ummmm ok. This is why this girl is my friend and not my girlfriend

There’s absolutely nothing wrong with hitting the pub for a few pints and the seeing if your beer goggles provide a bit of social lubrication…providing this is what you enjoy on a regular basis.

Shipwreck has tried many first date ideas -

• telling a chick you’re taking her skydiving even though she has a boyfriend (didn’t even get off the ground)
• a romantic river cruise on a small old charter boat with only my date and a captain (she lasted 2 weeks)
• drive-in movie theatre with me and my date dressed like Danny and Sandy from Grease (she decided to invite all her friends - that relationship didn’t even start)
• going to the cinema and sharing a big tub of popcorn (that one didn’t last either…how can you expect to get to know someone where you’re at the cinemas?)
• going for a long walk along the river and surprising the Sharon with flowers and a baby dolphin that appeared right infront of us (that lasted 3 years)
• teaching a Sharon how to play Britney Spears on the piano over the course of about 3 lessons (that lasted 18 months, but was rougher than bumper cars on steriods)
• dinner at my place (ok so far! - and I certainly aint no Jamie Oliver)

In my experience, the relationships that lasted the longest are the ones where the first date was the most relaxed and very ‘me’. Yes Shipwreck can be crazy sometimes and suggest ideas like skydiving, but unless you’re an adventure junky (which I’m not exactly) these extravagent first date ideas don’t normally work. Be yourself and choose something that is reflective of you!

First Date Sex
If it’s sex on the first date that you’re after, you’re probably not going to have a lasting relationship with that person. Besides…if you want to keep a guy like a dog on a leash, give him something to look forward to…and drag it out as long as you can!

First date sex is like giving up without a fight/chase. The guy will think you’re too easy and lose interest, he’ll probably think that you do it all the time which would be a turn-off, and there’s a good chance he’ll be bragging about it to all his mates - which you then have to face if you become his girlfriend.

As a male, one of the funniest things is watching mates go out on numerous dates with girls and get nowhere. So for the sake of giving us guys a good laugh…no sex on the first date please ladies.