What to wear on a first date. Or not

Christine RetschlagFashion 20 Comments

Editor’s note: It’s been a while since I’ve been on the dating scene. Today I’ve got Christine from The Global Goddess sharing her witty wisdom about what to wear when playing the dating game.

ALLOW me to divulge my dirty dating secret. I only own one “date dress”. That’s right. Uno.

Don’t judge me, there’s a method to my material madness and one which has served me well during my sassy single years.

As a brief backgrounder, I wasn’t always single, in fact, I was in a 22-year relationship (and married for four of those) but that all ended sadly and suddenly six years ago. And out of the blue, at the age of 38, I was back on the “market”. I resisted internet dating for the first four of those years, convinced Mr Amazing was right around the next grocery aisle corner (yes, you can laugh now), but in the beginning, I had a blast. While there are many horrible things about divorce, the one great benefit is what I like to call the divorce diet and overnight I lost a kilogram of weight for every year we’d been together.

That’s right, 22 kilograms. Life being the crazy funster that it is ensured that I had never looked hotter, when I felt at my absolute worst.

But that weight loss served me well and I could pretty much wear a paper bag and look half decent. Eventually, the happier I got, the more the weight crept back on and so did the years and before I knew it, I was clicking on that internet dating button like a woman possessed, convinced again that Mr Amazing was just one tap away (yes, please do laugh).

And four years after my desperate dating journey started, I began to apply the things I had learned about what to wear on a first date.

Lesson One: The clothes that women like to wear (eg: maxi dresses and boyfriend jeans) are out.

Lesson Two: Don’t bother spending one red cent on sexy underwear, 100 percent of men are only interested on what that sexy underwear contains.

Which leads me to Lesson Three: Cleavage is King. Of the entire empire. Sometimes, when I’ve been tired of the whole damn dating game, I’ve thought about just popping my boobs in a cab on their own and sending them out of my behalf, while I stay home, drink fruity cocktails, and watch a Disney flick.

Based on my “market research” I eventually came up with my one date dress. It’s silky, it’s strappy and it suggests cleavage. But not too much. It highlights my waist while falling elegantly to just below the knee, and kind of floats in a hippie way, which I like to think makes me appear flirty and fun (or I could just look like a hapless hippie).

Oh, and it’s a pretty purple. It’s a winner, it really is, the only problem being the men who have seen me in this dating dress, frankly, are not. And hence the need for just one dating dress.

Over time I’ve realised that what I want in a man, and what actually exists on the current Australian dating market, are vastly different and so, in a twist of fate, I’ve never had to buy another dating dress. Because I’ve never progressed things beyond the first date.

Yes, I’m kind of like that Kathyrn Heigl movie 27 Dresses in reverse. There’s been 27 dates, at least, but just one dress.

At this point, I should add that men don’t seem to worry about what they wear on a date. I’ve seen it all, I really have, including the bloke who turned up not with the sandy surfie hair his internet dating photo promised, but with short grey hair, looking 20 years older, which made sense, because he admitted the photo was 20 years old. And there I was, worrying about wearing last season’s nail polish.

Things did get a bit tricky earlier this year where I actually progressed things to four whole dates, and I had to rush out and buy a few back-up outfits – The Supremes to my Diana Ross – but when I realised he kept turning up in thongs (not the only thing wrong with him, but the easiest to explain), The Supremes and me packed up our pantsuits and went home.

And I haven’t been on a date since.

There’s actually a couple of reasons for this, but apart from the fact I’ve had a heady year travelling for work, I don’t particularly like to date in winter (my purple frock is strictly a warm weather affair).

Winter is for comfy jarmies and hot water bottles and red wine in bed. And in the height of summer, in sub-tropical Brisbane, my hair frizzes so much I look like a sucked mango. Which pretty much leaves me with autumn and spring. And so here we are, in the “season of love” and I’m about to dust of the old dating dress again.

In the meantime, I’d love to hear all your suggestions for the ideal date dress, and if you have any tips on finding Mr Amazing, I’d love to hear that too.

SY’s date dress shopping suggestions

 First date dress suggestions1. Gracie Dress $255 @ Birdsnest | 2. Kate Drape Tie Dress $249 @ Sacha Drake |3. Dannii Minogue Metallic Cocktail Dress $79 @ Target |
4. Moulded Peplum Dress $129 @ Country Road | 5. Chrissie Swan Wrap Dress $39 @ Big W

Christine Retschlag is an author, blogger and freelance writer. The Global Goddess is targeted at strong, smart, sexy and spiritual women (and the great men who love us!). To read more about her dating disasters, travel tales, and spiritual journeys, go to www.theglobalgoddess.com

Comments 20

  1. Just before everyone gives up on Internet dating, I would like to reveal that I met Mr CAGG on an internet dating site. There is gold in them there profiles! My go to dress was a black wrap dress that made me feel like a million bucks – ironically I was not wearing that the day I met him. Internet dating was certainly a journey and not for the faint of heart.

  2. I don’t get rule #1 – wear what you feel comfortable in.

    I gave up on dating. There are so many weirdos out there and it’s just a horrible time sink. I don’t understand what some of these guys think they have to offer, not because of superficial reasons but that they put zero effort into the whole thing. If they can’t put on a decent outfit and act like they are interested on the first date, they aren’t getting any better.

  3. Mr. Amazing usually comes along when you decide you are going to focus on being single/ arrange to move into a convent etc.
    The dating thing can be wearing and it is tough out there.

  4. It’s long time since I went on a first date, but I’m sure I can come up with another reason to purchase that stunning Sacha Drake dress.
    As for tips, I’d say be yourself. It you’re not a dress girl then wear jeans and a top that still provides the cleavage impact you’ve suggested. I wear dresses to work very often, but I socialize in jeans and heels and that’s what I wear on date nights with my husband, too. That way you’re presenting the real you and as is mentioned by others you’ll be more comfortable that way, too.

  5. Purple has to be a winner, in my book. Wonderful funny post, Goddess – and I wish you well in the hunt for that elusive perfect-for-you man.

  6. What a gorgeous girl you are I do hope you find Mr Amazing or someone that is lovely I can’t help you sorry I have been married for 29 years! I do know other people that are on the dating scene and it’s hard some of the things men ask I cannot put on here ,but you probably already know.
    I think you should dress for you comfy and chic and I love dress 2 and 5 and good luck Christine X

  7. A woman needs a man like a fish needs a bicycle! 🙂 Love the visual of the boobs in the cab. Great blog. Slightly sad, very funny and with great wardrobe tips. Much love x

  8. Oh, I am so with you Christine. I have been playing the dating game for about five years now, with an intermission here and there. Only one date in all that time progressed beyond the first (six months until I found out he was just not interested in dating one woman at a time). My date dresses are all V-neck and knee length. Other than that, I would say that the only other thing to wear is your confidence. But none of it means anything when you realise it’s not going any further. I don’t have any tips to find Mr Amazing however my policy is that you just focus on being fabulous and things will change.

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