Do you own a first date skirt?

by singlemomseeking on March 26, 2008

skirt.jpgThis week, at Single Minded Women, I say that “every single mom needs a first date skirt.”

But I can’t take credit for this advice. It was my single mom friend, Arden, who gave me this tip very early on, when I was terrified to go on one of my first dates as a single mom, and didn’t know how I’d ever afford new, glamorous dating outfits.

Every girl must have a first date skirt,” she said.

The brilliancy is: you don’t have to spend money on a new outfit for every first date… and this guy has never met you before, right? He doesn’t know that you wore this skirt last Friday and the Friday before.

My first date skirt is knee-length, sequined, and turquoise — a birthday gift from one of my best girlfriends in New York City. But it’s now so frayed that I should retire it!

To me, a first date outfit is absolutely comfortable, flattering, and something you feel good in. On my first date with the Biologist, however, I wore a white dress and this huge headband over my forehead because I’d slipped off M’s bed the wrong way that morning and had a Frankenstein scratch down the middle of my noggin.

I told him all about it, and his empathy touched me just right. He said something to the effect of getting so used to seeing me with the headband, it would seem strange to actually see my forehead the next time. I laughed.

Tell me: Do you have a first-date outfit?

Jeans? A sexy dress? A sweater and chinos?

If you haven’t gone on a “first date” as a single mom, what do you think you might wear?

And single dads: Do you have a first-date outfit? Do tell!

Image courtesy of JMarco

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{ 18 comments… read them below or add one }

KC October 7, 2009 at 8:57 pm

Leslie, a friend of mine had a similar issue. She mentioned was brought up to hate skirts by her mom. She eventually found an article on-line about why women do not get second dates (query “boss lady date” to find the article). In addition, she spoke of a quiz a friend gave her which changed her perspective, here is a poor attempt to recreate it:

1) During the day what are you wearing? most likely jeans, black or tan pants. Look around. All the other ladies and the men are all wearing them as well. Blending in and being androgynous works in the work place, but not on dates! He does not want a co-worker or a thin feminine guy for a date, he most likely wants a women who looks comfortable being one.

This of course pissed her off. Why should women have to dress feminine for men. They should like you for you.

So then the second question came up.
2) Visualize the man you find most attractive in the world. Now imagine him in a pink lacy dress. Still find him as attractive? Would you find him more attractive if society said it was ok for him to wear a pink lacy dress, make-up and heels? What if he wore a polo over it? no? Then why think he should find you as or more attractive when you wear clothes similar to what he does every day?
3) Feel entitled to wearing pants? Its a date, and many, MANY people think dates are all about them. Dressing more feminine may show him your comfortable and confident in your skin (or not, some guys do not notice), but dressing for yourself instead of him often smacks more of selfishness and self-righteousness than interest in him.

So she tried out wearing a skirt on the next few dates (and following a bit of the boss lady articles advice) and got second dates right away (she is now engaged).

Most good guys will like you for you, but also generally want someone who likes being feminine (just like you could like a guy who wears pink dresses for his personality, but it might be a turn off in early dating).

That said, boots are awesome!


singlemomseeking October 8, 2009 at 8:55 am

Wow, @KC thanks! Love this visualization.


Francesca April 1, 2009 at 11:49 am

My grandmother used to laugh and say – “you don’t need to change your clothes, just your friends.”

Francesca´s last blog post…The hunks come out when you’re in Hollywood


singlemomseeking March 29, 2008 at 9:15 am

Dan: Thanks for pointing this out… it’s not really what a woman wears.

Leslie: I hear you about the boots! I don’t feel comfortable in heels. But boot, mmmm.

America: First-date dancing shoes… are for dancing, right? Wow, I’m impressed by anyone who can do the Tango.

Judy: I love the idea of wearing something you made!… And the no-shaving-before-the-date. Good one! Cracked me up.


Judy March 27, 2008 at 9:14 pm

long skinny scarf (knit by me for possible conversation, and fun wrapping and teasingly unwrapping)
hoop earrings,
an arm full of bracelet’s (a great distraction)
and in between it all is usually
a short skirt
tank top with some type of over top (sheer, blazer, too long unbuttoned blouse) but they all are the same length of the skirt

yet more often I am going for black leather jeans. in lieu of the skirt. While they are comfortably sexy and can be worn year round they allow a girl not to wax or shave before that first date. It’s a trick learned. If your legs are not silky smooth you will not have sex him him on the first date….it actually works for me!

and never a hat till later on….


C H March 27, 2008 at 1:25 pm

Dear Rachel,

I do have a Black Watch tartan kilt. I doubt that I’d wear it on a first date, though. It might be too intimidating for my date to have a 6′ 4″ guy wearing a nicer “skirt” — woo-hoo.!

So I’ll probably just put on my black and white Punisher t-shirt and a pair of 501’s socal style…my kids like it. 8-)P


singlemomseeking March 27, 2008 at 6:35 am

Love it Cara! Beautiful! I want one!


Cara Hurley March 27, 2008 at 12:04 am

Hi ladies,

I just found a gorgeous skirt that reminded me of the pink one above.

Check it out:

Do you like it?




Kat Wilder March 26, 2008 at 10:15 pm

When I was doing a lot of online “meets,” I had a no-brainer outfit that I knew would always: be clean, be pressed, fit great, work day/night — in other words, it didn’t require a lot of energy on my part.

I needed my energy to, you know, be natural …

It was never the wrong thing to wear, and as I recall, one time it was the really perfect thing to wear. Because now when I see it in my closet, I have some amazing memories. 😉


Dan March 26, 2008 at 6:26 pm

Truth be told…I’m not really looking too deeply at what the woman is wearing on a first date…well…unless its something that’s suppose to get my attention. Generally I’m drawn to the woman face/eyes/lips…I’m sure there’s some subconscious evolutionary reason for this…attraction queues maybe? At any rate, as the date goes on I will start to notice the finer details…”wow, her ears are big” or “she really has boney hands…they look like bird claws” or “hmm…I should have ordered the salmon”. It’s my opinion, woman dress for themselves and other women. As I said earlier, the only time I take noticed of a womans outfit is if it’s highlighting/enhancing some particular asset. ;b


America March 26, 2008 at 3:04 pm

I am a long time lurker. I haven’t ready your book yet, as I just got a copy this weekend via the fabulous Solo Mother but am looking forward to diving into it now!

I am a social tango dancer/ instructor so alot of my “work” clothes are great first date clothes (though some are a little too extreme). I am a skirt girl so I will wear a skirt, no matter the occasion. I have soooo many skirts that can be dressed up or down so unless it is an active date like hiking (which I probably wouldn’t do as a first) I have something that fits the mood. I have more trouble with shoes since I am loathe to wear my nearly $200/pair dance shoes out and about. Besides, showing up on a first date in cheetah print stilettos might convey the wrong message 😉


Leslie March 26, 2008 at 11:52 am

I’ve only *had* first dates so you’d think I’d have an outfit by now. Mostly I’m a jeans and v-neck sweater kind of a gal. As long as I’m rocking my tall black boots underneath, I feel good 😉


A Mama Here March 26, 2008 at 11:01 am

No first date outfit-BUT, I did go out a buy myself a nice black bra from Victoria’s Secret to wear on dates. This was purely for me—just knowing that I was ready to date again and proud of it! The black bra made me feel extremely sexy and womanly!


Dr. Leah March 26, 2008 at 10:02 am

Hi Liz,

Looking forward to seeing you buy; please do post a picture after you’ve made the purchase.


Cara Hurley March 26, 2008 at 9:47 am

Oops, forgot to answer your question. My first date outfit is this pair of Jeans from Miss Sixty that I have had for about 5 years now. They are a perfect fit.

I don’t want to wear them to my next first date though. I want to be all girly and wear a skirt or a dress. I would probably go for a skirt, as a dress is well…I don’t know…too girly.


Cara Hurley March 26, 2008 at 9:45 am

Oh. My. Gosh.

That pictured skirt is so absolutely beautiful that I think I might just wear it to my next first date.

Without a shirt on. Or bra for that matter (in an ideal world).

It just shines on its own!

PS: I am a closet nudist so don’t be alarmed.




Andrea March 26, 2008 at 8:38 am

Most of my first-dates are from online dating, and it’s a chat over coffee, at which point a skirt feels slightly overdone. I usually go for flattering jeans and a nice shirt.

I haven’t actually had any dates nice enough to wear skirts for yet. My skirts are languishing in my closet. (sight)


liz March 26, 2008 at 7:57 am

My divorce isn’t quite final, so I’ve been putting off returning to the dating scene.

But after reading your book (LOVE it!) and now this, I think I am going to start shopping for a first date skirt. I love wearing skirts anyway — dress ’em up, dress ’em down, comfy, what’s not to love?!?. I’ll post a picture when I find one. And I’ll be all ready when first date time rolls around.

Look forward to hearing from others!


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