Why I Wear the Same Outfit on Every First Date

Like most thirsty Millennials, I’m on multiple dating apps. I’ve been using them for all of my adult life and I’ve met nearly all of my partners via the internet. The period of time between my initial interest in someone and going on an actual date with them is important to me. I wasn’t exactly looking for the straight hookup one would find at a site like Fuckbook, but I also couldn’t see myself ever having the whole “meet cute” experience of bumping into a stranger and somehow letting that develop into a romance. I need time to mentally and physically prepare for a date the way one does for a job interview.

All my dating profiles mention how I get nervous around strangers. The truth is, I have pretty severe social anxiety. Unfortunately, I also have an extremely high sex drive. The combination of these things means I tend to go on a lot of dates, but I sometimes struggle with keeping my cool. To help combat my date-anxieties, I have some standards for almost every date, including almost every aspect of my outfit. 

Most people have a favorite outfit–something they feel confident in. For someone with low self-esteem, I struggle with finding the right outfit for an occasion that makes me feel secure in how I look. Instead of having the pre-date montage of trying on outfits and pairing them with the right shoes or makeup or hair style, I stick to a script that works for me. It takes the anxiety out of the first scary part of any date: figuring out what to wear.

I find that having my outfit already planned out for each first date I go on helps calm my nerves. I can focus on getting ready without the added anxiety of self-doubt. Instead of questioning my outfit choices, I remind myself that my first date outfit is a staple for a reason–I look damn cute in it.

The Look

Dress: My “first date dress” is one of my favorites–if not my favorite dress. It’s a black sundress with Ariel from the Little Mermaid in a tattoo style all over the dress with floral and nautical details. This dress encompasses a lot of things that reflect my personal style and I feel comfortable in it. It doesn’t have sleeves, which is great for summer but I do add a thin grey cardigan when seasonally necessary.

Panties: I don’t go into every first date with the intention of having sex, but that has been a driving force in my adult dating life and some degree of sexual activity is often on the table if the date goes well. In this case, I have to plan ahead. I have very few sexy panties, in all honesty, but I do really love wearing a pair of black lace panties under my first-date dress. Even if sex isn’t on the table, it boosts my confidence to know I’m in panties that make my ass look great.

Shoes: I’m not good in heels for long periods of time, so as much as I’d love to wear this dress with a nice pair of black platform pumps, I go for a much more casual, comfortable option: a pair of black ballet flats.

Jewelry: I like to wear a symbol of my submission most of the time, but especially on dates. I usually wear a heart padlock on a linked chain for a little touch of classy kink to my outfit.

Makeup: My date makeup consists of tinted moisturizer, dark lined brows, a black or dark brown smokey eye, eye liner, mascara, and my favorite lip stain (currently loving Nyx’s Lip Lingerie in French Maid). My look is nothing too involved, and I tend to go easy on the smokey eye if it’s a casual lunch date but the thing that ties this whole look together, in my opinion, is the lips.

With this look as a staple, it takes a huge load of anxiety off me while I’m getting ready for a date. It’s also nice to be able to get from my shower to walking out the door for an impromptu date in under half an hour. Now, the hard part is figuring out what to wear on the second date…

This article was sponsored.
As always, all writing and opinions are my own.

xx SF