Monday, September 15, 2014

dating style & the BLOW OFF

I've said it before and I'll say it again. I hate dating. I'd honestly rather have a job interview or a root canal (OK maybe not a root canal, but at least with that you know the amount of pain you're in for. And you're prepared). Perhaps it is this attitude that has led me to my singledom, but after having survived one of the most painful situations ever, I've decided that I do want to be happy. With a good guy. I'd also like to procreate. So it looks like I'm gonna have to date.

Whenever I see happy couples, I literally want to stop them and be like "how did you meet and what is your secret?" It seems like meeting good people is especially hard in LA. I was listening to On Air with Ryan Seacrest, as I do every morning on my way to work, and they were discussing what to wear on a first date. Now I must tell you, I love Ryan Seacrest. He is witty, self deprecating, personable and he has a Labrador named Georgia. I truly trust and value his opinion.

*Note: I don't actually know Ryan Seacrest. I just feel like I do.

So I am one of those girls who most often either dresses for comfort or for other girls. Not in an "I kissed a girl and I liked it kinda way (though I sometimes truly wish that was the case), but in the way that girls often appreciate high fashion more than guys. For example I like high low tie dye dresses, rompers, and those flowy off the shoulder tops that I could probably wear during an entire pregnancy. In the winter my uniform is typically leggings, a cute sweater and boots. In the summer it's a maxi dress and sandals. And I will wear sweats and flip flops whenever I can get away with it. For two years I had consistent sex with a guy I loved who seemed to appreciate my love of soft sweat pants. That comfort level was one of the only nice things about that situation. And the sex of course.

Don't get me wrong, I still have some hot dresses and heels from my Hollywood club days and I will occasionally break them out for the Playboy Mansion or Corey Feldman's parties. However, those are special occasions and in my thirties, I am much preferring Lifetime movies, wine and my pajamas to the LA scene (which is one of the reasons I need to meet someone).

Now that you know all about my entire wardrobe, I will get to my point. My dear pal (well, in my mind) Ryan Seacrest was discussing what girls should wear on a first date. Basically skinny jeans, a tight (but not slutty) top and heels. Also, no peplum or anything fancy like that. Oh, and minimal makeup of course.

I've been doing this all wrong apparently. Now on a first date, I really prefer just drinks or coffee. I need an escape plan and I can't commit to a whole meal with a random stranger who might dress up as a clown in his spare time (this actually happened to me). So I usually wear a cute day dress kinda thing and sandals. I don't walk well in heels and wearing heels to happy hour or a coffee place just seems wrong to me. But now I'm thinking I should just suck it up and wear some skinny ass jeans and stillettos. But then I think, don't I want a guy who will like me for me? Maxi dresses, flip flops and all? Or do we need to dress to impress in the beginning and then we can whip out the sweats once they're all in. I'm so confused. I need your help.

So here are the questions I'd like to pose:

What do you wear on a first date?

Do you prefer to arrive to the date first or second? This is something else I struggle with. On all of my first dates, I've always been the first to arrive. I convinced myself I like this because I get to settle in and scope things out. But then I am constantly checking the door and my phone and maybe HE should be the one waiting and checking and the door.

Do you pamper yourself first? On one hand, I feel so great about myself after a trip to Dry Bar and a mani/pedi. But on the other hand, the more you invest in a first date, the more emotionally invested you are in the date being a success. Though this actually might not be a problem because it takes a LOT for me to become emotionally invested these days. But do I really want to spend $100 to look good for a guy who might dress up like a clown?

How do you get excited for a first date? I am usually anxious and 60% of the time I will end up cancelling.

So as you can clearly see, I am a girl who loves maxi dresses, sweats and Ryan Seacrest and I'm a mess when it comes to going on dates. Any help or insights would be awesome. Thanks in advance.


  1. I'm with you - coffee or a cocktail is the only way to go for a first date. That being said, as long as YOU feel cute in what you're wearing, that's what matters. If you're uncomfortable, you'll be miserable no matter how the date is actually going. And you're right - if a guy doesn't like you because you're wearing an outfit that YOU like then f**k him. Not literally because obviously he's a jag...
    Also, there's not much more disappointing than putting a lot of effort into an outfit only to show up to a date wearing a shirt with a big stain on the front. Really? Couldn't stop at the CVS for a Tide pen?

  2. That's great advice thanks! And you actually had a guy show up to a date with a big stain on his shirt? can i get a yuck

  3. This might suck to hear, but I'm married and still SO neurotic about what I wear out. The only good thing is that you can actually ask your significant other if something looks good or bad before showing up on the date, but I'm pretty sure my husband just tells me everything looks good cause he doesn't want me to go down the fashion vortex of trying on a million different outfits.