Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

And So I Went to the Date Naked

Saturday was a busy day for me.  I woke up and did some yoga (I’m currently practicing at home.  I’m still recovering/regaining my strength from my injury this winter.) and then did a couple of hours of work.  Then I took a few minutes to call a new guy I’d been chatting with from OKC.  He’d pretty much challenged me to call him first (‘not conform to traditional gender roles’ – his words).

So I called him and we had a perfectly pleasant conversation and after about 10 minutes I told him I needed to get back to work.  Then later in the day I went out for a walk.  It was a gorgeous day and I wanted to get some sun on my face (mind you, I wear sunscreen 365 days a year, so I never really tan).

As was the case on most Saturdays/days when I’m working from home and not planning to have any direct human contact until the evening hours, I hadn’t yet showered or washed my hair.  Just put on some clean(ish) clothes, washed my face and brushed my teeth.  In other words, when I left my apartment for my walk, I was completely naked.  Not a drop of make-up on my face.  Hair in a ponytail.  Old ratty sundress and flipflops.  Oh yeah, I was hot.

My phone rang about 30 minutes into my walk.  It was the guy from my phonecall. He wanted to know if I was available for an impromptu date.  A late lunch.  Right then.  I could have easily said no.  But the only reason I could think of for not going was because I looked like shit (how many 39 year old women do you know who would go on a date without any make-up?).

And so, because I think vanity is a sucky excuse for anything, I said yes.  I warned him in advance that I was out walking… He laughed it off (he’s one of those nature guys, always hiking and camping and stuff like that).

He didn’t vomit at the sight of me (I don’t look that awful without make-up).  And I was surprisingly cool about it the whole thing.  I thought I’d be nervous about it.  Self-conscious.  The whole way there I was afraid it would be weird.  But it wasn’t.  Maybe because I didn’t really like him much (I could tell within a couple of seconds that I wasn’t going to be into him – way too , even for me).

Anyway, I just thought it was kinda cool.  If you had asked me last week if I’d be willing to go on a looking the way I did on Saturday I would have said NO. But I did.  And I honestly don’t think it affected the outcome.  Although, I guess it’s possible he could have had a totally different personality if I was prettier?


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11 to “And So I Went to the Date Naked”


  1. Ian_P says:

    Hey, nothing wrong with women without makeup. It certainly beats women wearing excessive makeup which more often than not is just weird.

  2. jamyb says:

    So, what, after a certain age we’re required to wear make up? Or is it all the time? I’m 40, never wear it. If I remember, I might put on some lipstick for a date, but I usually forget. (I will sometimes put some make up on for a wedding, but that’s it.)

  3. 20forty says:

    I rarely leave the house without makeup even if I’m walking. Ridiculous I know, but as you said it feels naked. That being said, you’re a hella lot braver than I am. I would have said no.

  4. drumdance says:

    I personally prefer women without makeup, though that’s probably more a reflection of their general hotness. A girl who looks good without makeup usually looks even better with it as long as she doesn’t overdo it. Too much makeup is a huge turnoff.

  5. Vinkersole says:

    I usually only wear makeup to go on a date with my gf. Everyday shopping or just going out, I don’t bother with makeup. A little bit is fine. None is better than too much any day!

  6. Simone Grant says:

    First and for the record (and please I hope someone who knows me well writes in to back this up) I wear very natural looking make-up. I put on a little more for special occasions, but my everyday look is super natural. I don’t get women who look “made-up” in the middle of the day. I don’t really think it looks pretty. But then, beauty is in the eye of the beholder and I know there are men who do think it looks hot.
    -Ian_P
    I wasn’t judging other women. Just saying that this was hard for me. I don’t know what the male equivalent would be, but I started wearing make-up in my early teens. It’s a part of my self-image.
    -jamyb
    What about my post makes you think that I’m suggesting other women must wear make-up? This is about me and my choice. However, I don’t know any women my age who don’t wear it, ever. I have one younger friend (who is stunning) and she never wears any except for special occasions.

    It’s a choice. I wear it every day unless I think I’m not going to be “seen” by anyone or going to the park or the beach to sit in the sun.
    -20forty
    I don’t think it’s ridiculous to never go out without it. I think it’s pretty common. And I think I used to be more like that. I’ve become more comfortable in my skin/my life in the last few years and now think nothing of running out of the apt in almost nothing, no make-up, hair tied-up. If people are shocked they can bite me. Actually, considering where I live, I’m sure no one notices. And that probably has a lot to do with. As to being brave, I don’t know how brave it was, but I am kinda proud of myself.
    -drumdance
    I hear guys say that a lot (some of my exes,, for example), but their eyes light up when I take an extra five minutes to go a little glam for a special occasion.
    -Vinkersole
    Honestly, I just think I look a prettier with a little make-up on. And I feel better/more confident when I have it on.

  7. Veka says:

    It’s all about how you feel. If makeup helps you to feel more comfortable, then wear it! If it makes you feel uncomfortable, then go naked! Who cares? You just gotta make yourself feel good.

  8. lostplum says:

    This is just another example of why you are such a confident beautiful woman! Only you could pull this off!

  9. iamalejandra says:

    I agree with Plum, only you could pull it off, on the other hand if I leave the house without showering and washing my hair I would look like an overweight Amy Winehouse, hahaha.

  10. starangel82 says:

    I say bravo. I think it’s great you decided to go to the date even though you hadn’t gotten all dolled up. Maybe if more women were willing to do this, then society wouldn’t have such a high standard for beauty.

  11. Singletude: A Positive Blog for Singles says:

    This is such an awesome story! Good for you! I feel inspired. :)

    “Although, I guess it’s possible he could have had a totally different personality if I was prettier?”

    Maybe, but if so, you forced his true personality out of the closet on your first date, so you saved yourself the trouble of uncovering it later on.