Dating in Los Angeles: My Personal Guide to Crushing It

Hunter Lewis

If you don't know me, I’m Hunter from Wingman Plus. I'm sitting on over 1,000 + Tinder matches, and I’ve helped thousands of men around the world get more and better dates.

LA is a city I know inside and out. It can feel like a tough market, but that’s only if you don’t have a proven system.

If you're struggling for quantity or quality of matches on Tinder, Bumble, and Hinge, buckle up, bro. I'm about to give you my exact playbook.

LA is an extremely diverse city. With around 3.82 million residents, 35% of whom are foreign-born, and a median age of 37, the dating scene here is set against a rich cultural tapestry of people from all walks of life. 

Another unique feature of LA is that it is a hub for dating app usage. Nearly 3 in 10 U.S adults have used dating apps; however, these apps seem to completely control the dating world here in LA. Gone are the days when you’d find all your dates while out and about the city; you now need to combine smart app usage with real-world meetups if you want to maximize your dating experience. 

This isn't just theory. This is the ground-level strategy I use with my profile makeover clients. I’m going to show you how to build a profile that gets matches, how to text to secure the date, and exactly where to go to have a killer first date anywhere in this city.

My Non-Negotiable Rules for Dating in LA 

If you want to get the most out of your dates, you need to have non-negotiable rules. In a town like LA, where dating sometimes feels like it's getting more and more complicated, having these rules is especially important to make sure you A) turn those matches into actual dates, and B) increase the chances of the date being successful. 

Here are my non-negotiable rules that I uphold no matter who I am taking out: 

Rule #1: Respect the Geography

This might seem like a weird rule to someone who is not from LA, but we locals know that the Westside/Eastside divide is real. Asking a girl from Santa Monica to meet in Silver Lake for a first date is asking too much, and may discourage her from saying yes or showing up. 

If you want to increase the chance of the match turning into a date, respect the geography, no matter what. I always teach my clients that the best approach is to propose a venue at a reasonable halfway point, and that a 45-minute drive is a hard no for a first meet. All this requires is a little bit of research and planning. 

Rule #2: Use Time of Day to Set the Vibe

Ultimately, it is the vibe of a date that is going to determine whether it is successful or not. Many guys forget that the time of day can be a powerful tool to help dictate what the vibe of the date is, and forget to use it to their advantage. Or, they get it wrong and set the wrong vibe for the date. 

For example, organizing a weeknight drink is a low-stakes option, so it’s a great way to “vibe check” your date and see if you want to move forward. I use these dates to initially screen matches to see if we are compatible and if a second date is an option. 

Alternatively, a weekend date shows much higher interest, and while it's a great option once you’ve had those initial few dates and want to progress with someone, it can be a bit intense for an initial meet.

Knowing the difference between these types of dates and adjusting accordingly is a crucial way to ensure you maximize the dating experience and increase your chances of success. 

Rule #3: Master My "Day-Of" Confirmation

LA is the capital of flakiness, and almost everyone here has either been stood up or canceled on at the last minute. As a rule, I always send a confirmation text the day of the date to lock the plan in and save me from getting stood up. 

A simple “Hey, still on for 7?” text is a great move, but if you want to take it to the next level, I will often ask, “Hey, is it cool if we do 7:30 instead of 7? Just need to get my suits before the dry cleaner closes.” I find that women almost always run late and bail on dates because they don't have enough time to get ready.

This is a way of confirming the date with a better frame than asking for confirmation, and it reduces the chances of cancellation. 

Build a Magnetic Profile Using My Proven System 

Getting the matches you want starts with your dating profile. In the grand scheme of things, girls spend just a few seconds looking at your profile before deciding to match with you, so it's important that you make an impact from the very first photo. 

After a lot of trial and error, I’ve got profile building down to a fine art, and have figured out exactly what women want to see in a profile. 

My 5-Photo Mandate for Your Roster

Most guys use the 5-6 least crappy photos from their camera roll for their dating profile. That won’t cut it. Think about some of the best girls' profiles you’ve seen; did they have a couple of blurry selfies and a few group shots with their friends during their college days? 

Chances are the answer is no. Women are masters of photography, and if you aren’t putting the same effort in, you won’t be getting the matches you want. 

I'm going to show you how to build a photo roster that makes you look confident, fun, and like a guy who has his life together with my 5-photo mandate. And rule #1: get someone else to take your photos. Selfies scream, "I don't have friends."

Photo 1: The Clear Headshot

This is your money shot and the first impression you will make. Make sure it has great lighting, your hair and beard are lined up, and you have a confident smile. Avoid wearing hats and sunglasses together, as this stops a potential match from instantly seeing what you look like.

Photo 2: The “In-Action” and Hobby Shot

Women like guys who have a life, and this picture shows a little bit of your personality and interests. Whether you’re hiking, at a concert, or playing a sport, this is a great opportunity to create a conversation starter. 

Photo 3: The Full-Body/Style Shot

This picture shows you putting effort into yourself and having a strong sense of style. I tell my clients to wear a cool, layered outfit. It shows style and intentionality, and can also serve as your "confidence/edge" shot if you have a confident pose and a sharp look.

Photo 4: The Candid Social Shot

Letting your potential matches see what you look like when you’re out and about is great social proof of your personality. This should be a smiling, relaxed photo that looks like a friend took it while you were out having fun. 

Photo 5: The Animal Lover Shot 

Now it's time to show off your softer, nurturing side, which many women find incredibly attractive. Use a candid shot of you playing with or cuddling a dog. This is an instant green flag and a good conversation starter. 

Photo 6: The “Dressed Up” Shot

While not mandatory, this is the final piece for a truly complete profile. A photo of you at an event in a well-fitting suit or blazer shows you can clean up for a formal event, signalling maturity and success in a way that the other photos don’t. 

My Tech Tip: I use a Sony A7 camera for all my photos; however, this isn’t necessary. Just use Portrait Mode on a new iPhone, as it does an amazing job replicating the flattering look of my 85mm lens by blurring the background and making you pop.

The "Hot Boy Bio" Rule

If you’re writing a novel in your bio, you’re trying way too hard. The best men’s profiles all have one thing in common: they keep it short and sweet. 

My formula? All you need is one funny, playful, or interesting one-line. Your bio’s only job is to create curiosity, not to tell your whole life story.

One of my most successful bios is simply: “I probably have more tattoos than you.” It works because it creates a question she wants to answer. Add your neighborhood, and you're done.

How To Turn Matches into Dates in LA 

A common complaint I hear all the time in LA is that guys will have an inbox full of matches or be talking to a girl for months on the apps, but can’t seem to turn it into an actual date. 

Trust me, I’ve been there. However, I’ve figured out a few key steps to keep in mind to help you turn a match into a highly successful date. 

#1 Adopt My Buyer Frame

The most basic step is to adopt my buyer frame and stop trying to sell yourself. The person asking the questions is in control, so ask your match playful questions that make her qualify herself to you. 

#2 Keep Texts Concise

Flirting via text doesn’t require you to write a novel. Your text bubble should never be bigger than hers, so keep your messages short and sweet, and match her energy. Would James Bond send a paragraph? No. Neither should you.

#3 Avoid the Pen Pal Trap

A common trap many guys fall into is using texts to have deep and meaningful conversations with their matches. Texting is for logistics and building interest, not for exchanging life stories. I steer every conversation towards meeting in person, and find that this yields a much higher match-to-date success rate. 

#4 Stay Playful & Flirty

Staying playful and flirty is key. I use light teasing from the very first message to build chemistry. Dry, platonic texts get you put in the friend zone; fun and flirtatious banter gets you a date. 

#5 Create Value with Scarcity

No matter how tempting, I never reply instantly, as it signals you have nothing else going on. Your time is valuable, so act like it.

#6 Be Persistent, Not Needy

No woman likes a needy texter, but being persistent if things run dry can still be important. 

If she ghosts, I might send one lighthearted follow-up like "Good talk," and that's it. Chasing low-interest women is a waste of your time and not worth pursuing for a date. 

#7 Don't Rush the "Ask" 

Rushing into asking for a date can be a major turn-off. I use my SIMP framework (Small talk, Intentions, Match energy, Phone number) to build comfort before I suggest a date. It makes her more likely to say yes and actually show up.

My First-Date Map: Go-To Spots by Neighborhood & Budget 

Here’s my personal list of spots that are perfect for a first meet, walkable, conversation-friendly, and never more than 90 minutes.

Eastside (Los Feliz, Silver Lake, Echo Park)

 DTLA & Arts District

  • $ (Artsy): Gallery hopping along Gallery Row and ice cream from a local favorite like Salt & Straw
  • $$ (Playful): Rooftop happy hour at Perch followed by vintage games at an arcade bar.
  • $$$ (Elegant): Tasting menu at Hayoto and a nightcap at a high-rise bar like 71 Above with skyline views.

Westside (Santa Monica, Venice, Culver City)

  • $ (Beachy): Sunset beach walk + tacos from a beloved local window like Tito’s Tacos. 
  • $$ (Chic): Stroll the farmers' market in Venice and find a wine garden on Abbot Kinney.
  • $$$ (Hands-On): A chef-led pasta-making class + finding a nearby speakeasy (the Del Monte Speakeasy is highly recommended.) 

Hollywood & The Hills

  • $ (Active): Hike to a Griffith Park viewpoint and take a smoothie stop afterward.
  • $$ (Nostalgic): A movie at a vintage cinema (New Beverly) plus a pie at a classic diner.
  • $$$ (Entertaining): A live show at the Hollywood Bowl, followed by a late dinner on a patio.

The Valley (Studio City, Sherman Oaks, Burbank)

  • $ (Retro): Bowling at Pinz Bowling, followed by milkshakes at a diner.
  • $$ (Casual Fun): Sushi crawl on Ventura Blvd and a round of mini-golf at Sherman Oaks Castle Park.
  • $$$ (Polished): Attend a (free) live studio taping and a classic steakhouse dinner at BLVD Steak.

Tailoring the Date: Pick-Your-Scene Ideas

To make the best impression on your date, putting in a little thought will go a long way. There’s no point in taking a girl who hates spending time outdoors on a sunrise hike, as neither of you will enjoy the experience. 

Here are my go-to date ideas based on the scene you and your date like the most. 

 For the Outdoorsy Pair

If you and your date love spending time in the great outdoors, consider going on a sunrise hike, tide-pooling in Malibu, or even coffee-shop hopping along a bike path. 

For the Arts & Indie Lovers

Arts and indie lovers have a world of options in LA, and there is something for everyone’s taste. Why not attend a gallery opening or zine fest, or go old school and attend a repertory theater screening? 

For the Food-First Crowd

LA is filled with foodies, and luckily, it is a food lover’s paradise. Food truck festivals and pop-up dinners are a great low-stakes date idea that will keep your stomach full and the conversation flowing. If you’re feeling really adventurous (and hungry), you could even try to do a ramen crawl throughout the city. 

For Sober & Sober-Curious Daters

More and more daters are starting to identify as sober or sober curious, and taking this into account when planning a date can be a thoughtful touch. Non-alcoholic-centered activities such as botanical tea bars, pottery classes, and museum days are the perfect choice here. 

For the LGBTQ+ Community

 Planning your date around neighborhood hubs like WeHo and Silver Lake gives you a multitude of date activities to choose from. Whether it's a drag brunch, taking advantage of the outrageous nightlife, or attending a queer art show, there is something for everyone. 

How To Stay Sharp and Successful 

So, you’ve made it to the date. Now what? The key here is to stay on your A-game the whole time and make sure conversation flows as much as possible. 

Here are my top tips for a successful date and to increase your chances of date number two. 

Go-To Conversation Starters for LA

To get the conversation flowing, forget the boring interview questions you’ve used in the past. The trick is to be intentional and specific. These are some of the LA-centric openers I give my clients that actually start a fun conversation: 

  • "Real talk: favorite neighborhood taco window? I'm always on the hunt."
  • "Have you seen the [current popular] exhibit at LACMA yet?"
  • "Okay, LA question: are you more of a coastline person or a mountain/hike person?"

#1 Rule for Banter: Keep it light and don’t go too deep, especially on date one. Avoid talking about exes and absolutely no complaining about the industry or your job. You're there to have fun, not to vent.

My Follow-Up Formula: Locking in Date #2

This is where most guys drop the ball. If the vibe is good, you need to lead if you want to secure a second date. I teach my clients to be direct and follow one of two methods depending on how the date went. 

  • The "Yes" Move: As the date is ending, say: “I had a great time. I’d like to see you again. Want to try that [rooftop bar/spot you talked about] next week?” This is confident, and it shows clear intent.
  • The "No" Move: If you're not feeling it, don't ghost. A simple, direct text later on is respectful. Something like: “Hey, it was nice meeting you, but I don’t think we’re a match. Wish you the best.” It’s clean and lets you both move on while still being respectful. 

The Art of the In-Person Date

Considering how much time we spend on our phones, many of us have forgotten how to make the most of an in-person interaction. Mastering the art of the in-person date will be a core component of your success, 

In terms of conversation, the number one rule many guys forget is to be present and keep your phone away. Once you get talking, ask questions about her, but tie it to the environment, for example, "This place is cool, what's your usual vibe?"

Additionally, make sure you stick to proper date etiquette. Keep conversation light and encourage positive vibes only. Steer clear of talking about exes or complaining about work. 

How I Avoid Dating Burnout

If you’ve spent several years in the dating scene, you know that dating burnout is real. However, this is entirely avoidable if you are strategic about it. 

My best strategy is to embrace the micro-date. I keep all my first dates to 60-90 minutes, which is enough to feel a vibe. If it's good, it leaves her wanting more. If it's bad, you're out quick.

I also implement a hard “two date” rule, and never schedule more than two first dates in a week. It keeps the process fun instead of feeling like a job interview and protects my time.

Final Word & Your Action Plan 

If you’re ready to turn your matches into dates, then stop with the guesswork. Dating is a skill, and this is your training manual. I've given you the exact system I use to get results. By building a killer profile, texting with intent, and being strategic, you can crush it in this city.

Now, let's talk about your action plan. I want you to do this today. Pick one photo tip and one texting law from this guide and apply them. Stop wasting time with a profile that doesn't work and start putting in the effort. 

If you want to skip all the work, you can always apply for one of my profile makeovers for men. Otherwise, drop your biggest dating frustration in LA in the comments below. Let's solve it.

WRITTEN BY
Hunter Lewis
After spending 7 years mastering online dating from his own struggles, Hunter founded Wingman Plus. Today, through his popular YouTube channel (14M+ views) and by transforming over 100 men with strategic dating strategies and profile makeovers, his mission is to help every client get straight to the results.

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