Daily Divas: Makeup in a Post-Dating World

Daily Divas: Makeup in a Post-Dating World


Photo: Aisha Singleton

Becky’s makeup: Denise Del Russo

Jess’ makeup: Lauren Cosenza

Last week, I introduced you to relationship experts Jessica Massa and Rebecca Wiegand, who penned the book The Gaggle and run the website The-Gaggle.com. These two told us DATING IS DEAD and gave it a proper funeral at their book launch. 

Now I fully get the concept because, well, being alive myself in this current day and age I’ve lived it. 

But what’s a post-dating girl to do in terms of her beauty look and overall style for all the non-dates she finds herself on?

As I mentioned, it’s not like we are getting daily blowouts or manicures and rocking our best soft smoky eye for any old chance encounter — or for a planned encounter in a set-up that doesn’t call for it. 

So I invited the girls over and along with Denise Del Russo created some simple beauty looks for the different genres of non-dates, all snapped for you by fab photographer Aisha Singleton.

Before we reveal those scenarios and looks, though, let’s first revisit the philosophy…

Lauren: You proclaim dating is dead and have gone as far as held a funeral for it. I love a bold declaration. But what do you mean and what are the implications for singles today?

Jess & Becky: When we say that dating is dead, we mean that traditional dating, as we’ve always been taught to expect it, is no longer the primary path to romance, relationships and love. If you are looking for love these days, you mostly likely will NOT find it by exchanging phone numbers with a new guy, going on candlelit dinner dates, and having a “DTR” talk after three dates! That’s just not what the modern dating landscape looks like anymore.

Instead, we found through our research that people are now falling in love via more ambiguous paths. They are soccer teammates who spent months flirting and becoming Facebook friends before ever hanging out one-on-one, or professional contacts who sat down for a networking coffee and found out that they had a lot more in common than just work, or old friends who spent years texting and emailing and suddenly felt a new spark one night and decided to explore it. 

This means that in this post-dating world, singles need to be open to discovering romantic connections anytime, anywhere. Even if you don’t have a date on the calendar, you likely have an endless schedule of “non-dates” happening – parties, work events, classes, casual hangouts, e-conversations simultaneously going with many people…and these non-dates are all opportunities for love. So singles need to stop simply asking themselves who they are dating, and start looking around at everyone they know and are meeting, in any setting, and exploring the possibilities for connection there.

Lauren: For the ladies who haven’t read your book or visited your site (yet!), what is a Gaggle?

Jess & Becky: Your gaggle is the group of guys in your life who you might not be dating, but who are playing some sort of role, fulfilling some sort of need, and helping you figure out who you are, what you want, and what type of guy and relationship you ultimately desire. These are the guys who are helping you to explore the many emotional, physical, intellectual, professional and spiritual sides of yourself – even if you’re not “dating” them in any traditional way.

Based on our interviews with women, there are ten roles that these guys might play in your life – everything from The Boyfriend Prospect (who you really like) to The Accessory (who is your platonic male best friend) to The Hot Sex Prospect (who you feel crazy physical sparks for) to The Career Booster (who supports your professional aspirations) and more. Once your throw yourself into these somewhat ambiguous relationships and commit to exploring these connections, your relationships with all the men in your life will improve, you will get to know yourself and your desires infinitely better, and you’ll increase your chances of finding love – and not any love, but the love that is right and perfect for you!

Lauren: So if you can’t count on a regular Friday or Saturday night dinner date, where can single men and women find — or be happily surprised by — spontaneous, albeit often ambiguous, romance?

Jess & Becky: Anywhere! We have heard pretty much every story under the sun, when it comes to where and how people are now connecting and falling in love. But as a general rule, the more you can get out there into the world and interacting with people, the better. Because romance can come in the form of the guy who makes your coffee every morning, or the co-worker who always gives you great notes on your presentations, or the friend-of-a-friend who is suddenly liking all your Instagram photos, or the guy you met at a bar and randomly made out with. 

If you look at every guy you already know and every new guy you are meeting, and consider him a potential member of your gaggle and proactively explore that relationship, then your romantic possibilities will increase exponentially and you’ll be having so much more fun in the process.

Lauren: Spontaneous doesn’t always mean effortless. If you never know you’re on a date — or a non-date, so to speak — should men and women try to look their best at all times? Or would that fall under trying too hard?

Jess & Becky: Men and women should make an effort to be happy with how they look at all times, so that they can be confident enough to explore new spontaneous connections wherever and whenever they appear. But that doesn’t have to involve trying too hard! Living in the post-dating world, having a gaggle and realizing that you are regularly on non-dates is not about revamping your life to be desperately seeking love. It is simply about adjusting your mindset to be living your life, comfortably and as you choose, while recognizing romantic potential every time it pops up. 

So, just because you’re open to connection all the time, that doesn’t mean you have to cake your face in makeup to hit the gym or spend two hours getting ready for work each morning. It just means that you should put yourself together in whatever way makes you feel confident and secure in the setting that you’re planning to be in. Nothing kills a potential spark like feeling unattractive or insecure, so just put in the effort to make sure that you’re walking around open to the world and feeling comfortable and happy in your own skin, and that will do the trick.

Lauren: We created four beauty looks for four types of non-dates and we pulled outfits based on clothing you had.

Photo: Aisha Singleton

Becky’s makeup: Denise Del Russo

For the active non-date (possible settings: the gym, an outdoor track, the next Tough Mudder), we love a barely-there fresh face created in just minutes with BB cream (with built-in sunscreen!), waterproof mascara, a touch of cream blush and tinted lipbalm. Paired with a pony and cute tee.

Photo: Aisha Singleton

Jess’ makeup: Lauren Cosenza

For the outdoorsy non-date (possible settings: a music festival, a pool party, a picnic), a golden glow in the form of bronzer or highlighter, shimmer lipgloss, metallic gold eye cream, soft brown liner plus waterproof mascara is perfect. Paired with a fun headband, undone braid and crochet top.

Photo: Aisha Singleton

Becky’s makeup: Denise Del Russo

For the professional non-date (possible settings: a lunch, a conference, a networking event), we recommend a polished look with flawless skin via light foundation, a touch of translucent setting powder, soft washes of neutral eyeshadows, precision mascara and a longwear lipstain. Paired with loose strands tucked behind one ear and a feminine blazer.

Photo: Aisha Singleton

Jess’ makeup: Lauren Cosenza

And for the party non-date (possible settings: a birthday party, a wedding, a happy hour), we’re down with some personality through color and texture choices like metallic eyeshadow, a flushed cheek and punchy lipstick (choices that will pop in low lighting). Paired with tousled waves and a fab top or dress.

What were your thoughts on the various looks we created for this post?

Jess & Becky: We thought that the looks were perfect for the non-dates! It was so fun to come up with the right makeup, hair and style vibes for each non-date experience, and to feel how shaking up your look can actually make you feel prepared and excited for the possibility of different types of connections in different types of settings.

As we said, showing up at the gym looking like you’re ready to hit the club can make you look like you’re trying way too hard (and is of course bad for your skin as well). That’s why Becky’s workout look was so great – if she started chatting with a guy at the gym, she was wearing just enough makeup to feel confident and attractive while still allowing herself to feel comfortable and in-place in the gym setting. She could be low-maintenance and gym-appropriate, without feeling naked and like she needed to lower her head and hide in the locker room.

We loved Jess’s casual-but-trendy look for a concert group-non-date. You could easily imagine her at Coachella or Bonnaroo, hanging out with her friends and having fun with the guys in her crew (and the guys she’d probably end up meeting at the food stands). It was the perfect flirty, playful daytime look. 

Becky’s networking-non-date look was perfect for a meetup with a cute professional contact. She looked professional but also feminine – great for the coffeeshop, but also great for an after-coffee drink, if the conversation turned out to be even more fun than she was expecting. You never want to look too overtly sexy when there’s a professional component to a non-date – but you always want to feel attractive and able to kick things up a notch, if the night spontaneously continues!

Finally, Jess’s nighttime look worked great for that friend-non-date that you’re hoping to turn into something more, or that birthday party group-non-date where you’re hoping you’ll meet some great guys. Because it took place at night, it was fun to play around with a more colorful look that still felt authentic, but also amped the sexiness up a notch. Any look that would be great for a traditional “date night” will also be perfect for this kind of who-knows-what-will-happen nighttime non-date!


What are your thoughts on non-dating? Do you have a go-to makeup look that works for any and all occasions? Got a relationship question for Jess & Becky or a beauty question for Denise & I? Join the convo and share with us in the comments section below! XOLC