How Long Should You Wait to Dress Down In Front of a Man You’re Dating or “Talking” to? 👀

Let’s discuss the new age of dating and relationships. Whether it be a swipe & match on a dating app or you met your person at the local grocery store, there are always stigmas and rules when it comes to dating and during the process of a man courting you. I want to discuss one that was recently brought to my attention. The timeline of when you should start dressing comfortably/down or “raggedy” in front of someone you’re dating, whether it be during the process of courting or after and vice versa. Now, I know that this has been a topic of discussion in the media before, but I wanted to talk about different perspectives and share my opinion about what I think regarding this “timeline”. 

According to Sleep News, over 1/2 of men relax their physical appearance after 6 months, compared to just 1/4 of women. Most women like to keep up a pristine appearance for at least the first year of a new relationship. Instead of this marking a turning point in couples’ romance levels, it would actually signify timescales when both partners begin to relax and be themselves. Perhaps revealing the ‘real’ you – in sweatpants, a frumpy sweatshirt, and faded shorts – marks the juncture when the initial highs of falling in love die down, but the fires of true love are first lit.

“Put lipstick on even when you go jogging!” admonished “The Rules,” the best-selling, unabashedly old-fashioned dating guide first published in 1995. In a 2012 edition of the book, authors Ellen Fein and Sherrie Schneider encouraged women to dress up for dates and even when not on dates. They wrote, “If you walk around in any old clothes on the theory that what counts is only what’s inside, not your outside, think again! Men like women who wear fashionable, sexy clothes in bright colors.” Millions of women have followed the Rules over the years, and some still post triumphant tales of their engagements, and in one case, a photo of her ring, to the review sections of the books’ Amazon pages. Although “The Rules” has often been criticized for its retrograde strategies, the concept of looking somewhat polished for dates and thereafter is widely accepted. I mean, duh why wouldn’t it be? It’s literally what we are conditioned to do! but, the latest buzzword in online dating is “authenticity,” and with that comes a casual new dress code. Let’s get into it!

In the age of online dating, this often manifests as glamorous profile photos, and dresses, and blowouts for dates. But some women are trying the opposite tack. There seems to be a new rule circulating: Dress down—WAY DOWN—to make a more forthright first impression. Try a no-makeup profile photo for dating apps or show up for a date in sweats.

Courtesy of THE WALL STREET JOURNAL, I want to tell y’all the story of Amy Nobile.

When Amy Nobile’s marriage fell apart in 2018 after twenty years, she suddenly became a 49-year-old single mom to two teenagers navigating the dating scene in New York City. Ms. Nobile, who has co-authored four self-help books, began online dating, going on as many as four to six dates on some days with men she met through apps. Although she was mostly enjoying herself, the physical trappings of these dates felt oppressive. Why spend hundreds of dollars and precious time to dress up and get your hair and makeup done, just to slug wine during dates (some of which she termed “hellish”) with random fellas from Bumble? Plus, were they even seeing the real Amy? And so she “cracked the code” as she puts it, by coming to dates in athleisure, applying minimal makeup and minimal effort. Ms. Nobile found her new partner using this no-frills approach three years ago. She explained, “When I met Brett, it was at Joe & the Juice on the Upper East Side and I was in Lululemons and, you know, I felt comfortable.”

Ms. Nobile launched a dating coaching business, ‘Love, Amy,’ in 2019 to help other people find love. And one of her most unorthodox strategies was born out of her own experience. For the first meeting with a match, she advises clients to come straight from a workout (or the couch), barefaced, and without artifice. She calls it a “mini screener date”: 30 to 45 minutes for coffee or an early drink. The idea is to economize your time, money, and effort, but also to manage expectations. “It’s low stakes and you’re in charge,” said Ms. Nobile. She said that the “casual vibe” meant that “you can feel grounded and you can feel authentic to you.”

Great story, right? Ms. Nobile obtained a partner solely by being the only thing she knew how to be…herself. Now, I want to talk about another woman that is similar to Ms. Nobile, Julie Samuel. A 32-year-old woman, working as a recruiter and living the single life in New York City. She used to dress up in heels and nice jeans for fancy-drinks dates. But then last year she consulted with Ms. Nobile, who told her, “You’re not meeting people who want to get to know you—they’re getting to know this perfect version of you.” Ms. Samuel took the advice to dress down and immediately saw its wisdom. She said it helped her “weed people out faster” by breaking down any walls and getting to know them in their normal state. She didn’t dress up for her current partner until four months after they began dating when they attended a wedding together. She remembers, “I turned to him and said, ‘This is totally the opposite of every other relationship I’ve been in. The first time you’re seeing me dressed up is when you already love me.” Ms. Samuel mused that the “Love, Amy” approach was focused on “values.”

“If you want someone to love you just as you are in your purest raw form then that’s what you present.” If your purest raw form wears sweatpants instead of miniskirts, by all means let her out.

Amy Nobile

What do y’all think? How soon is “too soon” when you begin to dress “down” around a man? And do you agree with the backwards approach of dressing down during the courting process and then dressing up once the man is secure? Let me know! 🤍