Ask the Dating Queen: What to wear?

Part of an ongoing, periodic series in which the illustrious Dating Queen (that being me) draws on her vast dating experience to answer the questions of readers in the most queenly of fashions.

In other words, I'll blather on about what I think, and you're free to take it or leave it.

No, I'm not a therapist, but I've done a lot of dating (seriously, in one 2 1/2 year stretch I dated 57 men, which by default makes me something of an expert), and I've got me some opinions, which I'm oh, so happy to share.

Wanna play? Just click here and send me your question. I can't promise an answer to every question I receive, but I'll respond to your email regardless.

Now, onto today's question!

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Dear Dating Guru!

Well I have a date - yikes!
What does one wear for a first time meet and greet - possibly drinks/possibly eats in the city...evening?

Signed,
Pexperlexd With Nothing To Wear

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Dear Perplexd,

Ah, yes, the old What-To-Wear-On-The-First-Date dilemma. I know it well.

Rhetorical question: do you think men put more than one whit's thought into this? Do you think they even put one whit's thought into it?

Well, okay, the metrosexuals do, God love 'em. But the rest of them? (And this is the breed – ie, the Fashion-Oblivious – that I seem to have dated the most. Sigh..)

Well, annoying as it can be sometimes to have so many choices, it is in fact one of the pleasures of being female. I mean, can you really blame cross-dressers? Women's apparel is just so much more fun!

That said, it still creates some trauma when one is dressing for a date, especially a first date.

Dress to suit the venue

Here's the deal: it's not as hard as you might think to figure out what to wear. The real question is, what's the venue? If you know where you're going, you pretty much just dress to match, and you're good to go.

My rule of thumb* is to dress the same way I would to meet up with a girlfriend, but slightly more spiffified.

Examples:

• Going on a hike? Obviously you're going to ditch the fake eyelashes and opt for the REI look.

• Coffee at Starbucks? Think about what you'd wear to meet a girlfriend there, and maybe add a dash of lip gloss, if you don't normally wear makeup (or mascara, if you're eyelash-pigment-impaired like me).

• After work drinks at that chic new bar downtown? Dress up a bit, but don't go overboard. I'll sometimes wear a dressy top and heels, balanced with a pair of (nicely form-fitting) jeans. Or a dressy skirt with a jean jacket.

In your case, drinks + possibly dinner, find out where you're meeting, and if you don't already know the place, scope it out ahead of time. See if there are pics online. A homey sushi bar will require a different wardrobe than the trendy four star restaurant.

(I once met a guy for lunch at an order-at-the-counter lunch place, and he showed up in a suit. With flowers. Nooooo! Believe me, you do not want to make the equivalent mistake.)

Dress strategically

Whatever the venue, it never hurts to highlight your best feature.

• Cleavage? (NOT my area of expertise) Perhaps pick the slightly lower-cut top (slightly, because you don't want to look like a hooker).

• A nice rear view? Choose the form-fitting pants rather than the baggies. Good gams?

• Shapely shoulders? Go for a camisole or tank top, if the weather's warm enough.

Don't go overboard, and don't worry too much about it. Seriously. You want someone who's going to be totally into YOU, even when you're sick in bed after a sleepless night, right? Own your own particular brand of beauty and wonderfulness, and go into the date with the attitude that you're there to scope him out.

Remember, the important question to answer on date #1 is "Am I interested in going on a 2nd date with him?" Period.

If he's not interested, regardless of the reason, then he is SO wrong for you, and good riddance!

Good luck, and let me know how it goes!

Kisses,

The Dating Queen
aka The Dating Guru

*My high school history teacher told us that "rule of thumb" comes from the Middle Ages, when a man was allowed to beat his wife with a stick, as long as it was no thicker than his thumb? Though Wikipedia claims other etymologies, despite how traumatic dating can feel, aren't you glad you live in 21st Century America?

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