AWKWARD FIRST DATES ARE SO LAST YEAR. HERE’S A New Plan.

legs out truck windo

Sick of getting your hopes up on dating apps only to have everything come to a screeching halt on the first date? We’ve got a new plan for first dates, so get ready for it.

By Leslie K. Hughes

Thanks to the modern dating world, first dates have become a dreaded and, more often than not, failed event. After spending however long you see fit trading texts and pics back and forth on an app (in the 2020s that’s what we call “talking”), you finally take the plunge and decide to meet in real life. 


And when I say plunge, I really mean plunge. You are thrusting yourself into the great unknown; rolling the dice and hoping Lady Luck is on your side. 

Sure, someone may sound great via text; they may know how to say the right thing. They may have their photo angles down perfectly or, unbeknownst to you, may have relied heavily on edits and Facetune to make themselves look desirable, dare we say possibly even dateable if you’re lucky. 

If you make it past the catfishing stage of the first date, well congratulations — you’re one of few. And don’t think it’s just girls that catfish, guys. This fish definitely swings both ways. 

Having fun yet? Don’t get too comfortable, because the next level of the dating game that you have to beat is the world of small talk. 

Sexting with someone before you’ve met is a great way to let your seductive, sexy alter ego fly free, but when you come face-to-face for the first time with the person whom you’ve imagined doing the unimaginable with, chances are good you’ll feel like you couldn’t possibly sip your cocktail down any quicker. 

Which leads us to the next challenge: who is going to crack first and pay the bill? While I am of the belief that whoever initiated the date should be the one to lay down their plastic, I realize not everyone shares my perspective. So instead I’ll be here to wish you luck in the ring; may the best man or woman win. 


Time to Call in the Experts

woman in underwear holding phone
photo | @filthymouthcreative

Let’s call a spade a spade: going through all of this just to see if the person you swiped right on in a moment of ______ (insert: hungover, bored, drunk, blind, lonely) hope is someone you want naked in your bed feels absolutely absurd. 

I chatted with dating coach extraordinaire Benjamin Daly to get his expert advice on the subject. “It’s important to understand that dating is a numbers game. It’s like panning for gold — you’ve got to do some sifting to find your little nugget.” 

Well, there seems to be more fool’s gold than real gold in the dating pool, but as Benjamin shares: “This means you’ve got to be patient and be prepared for disappointment along the way — it’s all part of the process.”

Cue the “ugh” and eye roll combo. But don’t worry — there is hope. Here are some tips from Benjamin on how you can get past the dreaded swiping phase:

  • Know what you want. “Make a list of the qualities in the type of person you want to attract.”

  • Photo selection is key. “90% of the action will be due to your photo selection. Pick photos which show you looking your best, doing the things you love to do. The best combination is a close-up photo, a full-body photo, a social photo, an action photo, and a random photo of you doing something that will generate conversation.”

  • Make yourself sound fun. “The purpose of your bio is to communicate information about yourself that will get him [or her] interested in you and to facilitate a fun and engaging conversation. Describe yourself in a fun and unexpected way, leaving opportunities for questions to be asked.”

  • Unique is hot. “Highlight the things that make you unique. Most people present themselves in the same way online, so being different will set you apart from the crowd.”

  • Small talk is cheap. “Avoid small talk. Your opener should be a question related to something interesting about their profile. Then keep the conversation fun and light, with a focus around ‘you and them’ until enough comfort has been established and a first date is agreed.”

First Dates Get a Face Lift

woman getting lip injections for first dates
photo | @thetylershields

Speaking of first dates . . . You’ve gone through the treacherous process of finding someone you actually want to go out with, so that’s call for a “congratulations.” 

Now, instead of opting for an awkward drink or dinner date, I am rooting for team Group-Setting First Date. Whether this means bringing your date to a party, out to hang with your friends, or a group date with other couples, this is a refreshing alternative to the forced and uncomfortable one-on-one first date. 

However, it turns out that a group setting for first dates is not a fan favorite for everyone. In fact, I chatted with other dating experts who vehemently warned against it. In my opinion, it is far beyond time to throw old dating practices out the window and spice things up a bit. 

And, if you’re being honest, you’d give anything to avoid a hellish first date scenario like I described up above. Thus, enter: the group-setting first date.


How to Master the New First Date

man and woman holding hands through plant on first dates
photo | @we_are_hah

The first step in planning a successful group-setting first date is to “have a call or video call to get a feel for that person. Introducing someone you haven’t met to your friends could be uncomfortable if it’s not going to be a good fit,” warns Benjamin. 

If you’re vibing with that person from the call, then it’s time to extend the invite for the group hang. Just be sure to let your friends know. “It’s important that everyone in the group knows that it’s a very relaxed first date,” says Benjamin, “as you want to avoid the awkward ‘how long have you guys been together?’ question.” *Cringe.*

Now it’s time to rock and roll right into your date. While one of the fab things about this group date is the fact that there isn’t as much pressure to keep things moving all on your own, Benjamin feels you definitely need to, “set aside time to talk on a one-on-one basis. You don’t want to leave the occasion feeling as though you haven’t connected.” 

Also, you don’t want to leave your date too available for others to swoop in and steal him or her away. 

woman and man kissing with champagne spray
photo | @thetylershields

Group-setting first dates are like a big yogic sigh compared to one-on-one first dates. They alleviate the pressure of ensuring every. single. word. that comes out of your mouth is perfectly rehearsed and oh-so methodical. Talk about fake and boring. 

This fresh new style of date gives some room for slack, and also gives the opportunity to let the real you shine. Rather than hiding behind the fake persona you created on your dating app, the company of friends will make you feel comfortable in your own skin. And feeling comfortable on a date will go a long way, hopefully leading you two all the way to your comfortable bed.

So ditch the dated, dreadful drinks and/or dinner first date and opt for group vibes. Stop waiting for your dating life to change and get your ass in gear so you can get that ass. 



Benjamin Daly is a women’s dating coach who has worked for over 15 years to provide knowledge, strategy, and training for women to effectively date and form successful relationships. Daly recently wrote and published a book called “Appily Ever After: A Woman’s Guide to Online Dating” that you can purchase on Amazon. See more of his work at www.benjamindaly.co.