A Dating Challenge From Couples Therapists (+ Where To Take Your Date)

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There's no way around it: dating is tough. It's easy to get caught up in the stress and frustration of searching for a good match. But what if we told you that finding love could be more fun and less stressful? We've got some practical tips to make dating enjoyable, all while exploring San Francisco or Los Angeles. You can transform your dating experience by gamifying it and using it as a way to have enjoyable experiences.

Why Dating Mindset Matters

Dating can be a rollercoaster of emotions, often leaving us feeling discouraged. But what if we approached it as a game? By changing our perspective, we can relieve stress and rekindle our excitement. Each date you go on has something to offer, even if it doesn't lead to a lasting connection.

The One Date a Week Challenge

Whoa. One date a week? That's crazy.

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Yeah, we know. It sounds like a lot. But we want you to consider going on one date a week. It can be a real game-changer. See, dating is a numbers game. The more people you meet, the more likely you are to click with someone. If you're focused on simply meeting a greater number of people, your odds go up.

But that's not all you need. You also have to take the pressure off. We suggest treating dating a chance to meet new people and a way to experience your city. San Francisco and Los Angeles have endless possibilities for unique and memorable dates. From coffee shops to hiking trails to experimental theater, there are tons of places to explore.

Gamifying the Dating Experience: The List

Hold off before getting on the apps. Your first task is to create a list of 30+ places you've always wanted to visit. Coffee shops, open mic nights, comedy festivals, farmers markets, cooking classes, thrift shops, breweries, you name it. Make a list of 30+ things you'd want to do with anyone. Then slot in your weekly dates as opportunities to go to one of the places on your list. The goal is to have fun, regardless of the outcome. Treat your date as someone along for the adventure, not the sole reason for the outing. Even if the worst happens and you get stood up, there's something interesting to do. By turning dating into a weekly outing, you'll reduce the pressure and infuse a sense of playfulness into the process.

So before you do anything, make your list! We recommend starting with at least 30 activities you'd be up for trying. This is keep you from having to come up with an idea from scratch once you've secured a date. We often blank when we're put on the spot and suggest another restaurant or wine bar. We want you to be more creative.

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Exploring Your City Together

San Francisco and Los Angeles have tons of date-worthy spots. In San Francisco, consider a leisurely stroll through the Golden Gate Park, followed by a visit to the de Young Museum. In Los Angeles, take a drive along Mulholland and end your evening at Griffith Observatory for a view of the city. Both SF and LA have thriving comedy and arts scenes. The restaurant selection can't be beat. Remember, the goal is to enjoy your city and share these experiences with someone new.

Structured Dates for Meaningful Connections

It's easy to fall into the trap of the traditional dinner-and-drinks routine. Over a table, conversations revolve around self-introductions and personal anecdotes. Consider restructuring your dates around activities that take the focus off you and foster a sense of fun and connection. This approach offers an opportunity to experience your date rather than hearing about them. You'll get better information about who they actually are. It's a more revealing and exciting experience.

Ideas For Weekly Dates In San Francisco or Los Angeles

Creative Workshops

Consider signing up for creative workshops together, such as painting, pottery, or cooking classes. These classes spark creativity, and provide an atmosphere for getting to know each other. You'll discover shared interests and see each other's personalities shine through your collaboration.

San Francisco Workshop Date Idea: Take a glassblowing or flower arranging class

Los Angeles Workshop Date Idea: Take a mixology or woodworking class

Explore Outside Together

Take your dates outdoors and explore nature. Whether it's hiking through trails, paddling around a lake, or strolling through botanical gardens, these shared adventures allow you to bond over the wonders of the natural world. Nature provides a backdrop for meaningful conversations and a chance to see your date's adventurous side. Be sure to go to a populated area on a first date for safety.

a man and a woman in a rowboat representing a fun date idea for people looking for therapy for millennials in san francisco or los angeles

San Francisco Outdoor Date Ideas: Hike in the Presidio, boat around Stowe Lake, visit the Japanese Tea Gardens or Botanical Gardens. You can also pack a picnic and head to Ocean Beach.

Los Angeles Outdoor Date Ideas: Hike Runyon Canyon, paddle around in the swan boats in Echo Park, or picnic at Dockweiler Beach.

Visit Local Attractions

From museum-hopping to exploring historic districts, these excursions offer a blend of adventure and cultural enrichment. You'll both have the opportunity to share your thoughts on what you've experienced, deepening your connection. And if your date is a dud, there's something interesting to look at.

San Francisco Local Attractions Date Ideas: The Filbert Steps, The Walt Disney Family Museum, take a walking tour of Haight-Ashbury, or go to the Ice Cream Museum.

Los Angeles Local Attractions Date Ideas: Getty Villa, Venice Canals, Griffith Observatory

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Go To An Independent Bookstore

San Francisco and Los Angeles have some of the coolest bookstores in the country. With your date you can browse the shelves, get to know their favorite books, and flip through design or cookbooks and learn their tastes.

San Francisco Bookstore Date Ideas: City Lights Bookstore, Green Apple Books, Book Passage

Los Angeles Bookstore Date Ideas: The Last Bookstore, Skylight Books, The Ripped Bodice

Attend A Performing Arts Event

Both San Francisco and Los Angeles have thriving performing arts scenes. Even if you're not a theater or dance person, there's something for everyone. Both SF and LA often have summer arts festivals in local parks that are free to the community.

San Francisco Arts Date Ideas: Attend a play at A.C.T, a free performance at Grace Cathedral, or a standup show at the San Francisco Comedy College.

Los Angeles Arts Date Ideas: See an improv show at UCB West, attend a play at the Geffen or Wallis theaters, or see some live jazz at Catalina Bar & Grill.

Challenge Each Other

Consider incorporating a bit of friendly competition into your dates. Activities like mini-golf, go-kart racing, or even a trivia night at a local pub can be fun and help break the ice. The playful spirit of competition can reveal aspects of your date's personality that you might not encounter over dinner.

San Francisco Competitive Date Idea: Play minigolf at Urban Putt

Los Angeles Competitive Date Idea: Trivia night at Barney's Beanery

Volunteer Together

Being part of something bigger than yourself feels great most of the time. Choose a cause that resonates with both of you, whether it's animal shelters, food banks, or community cleanup projects. Working side by side on a shared mission creates a unique bond and allows you to witness your date's compassion and values in action.

By structuring your dates around engaging activities, you'll gain deeper insights into who they are. You'll also have more fun. Instead of relying on conversations, you'll create experiences that reveal their true essence. It's easier to have someone show you who they are rather than tell you. By making the dating journey more revealing, you'll have better information to make decisions about if you want to see them again.

When Dating Gets Discouraging

Dating can be daunting, and it's natural to feel discouraged at times. There are several reasons why this happens:

Rejection: Rejection is a part of the dating process. Facing rejection can hurt. It's important to remember that it's not a reflection of your worth or desirability. Instead of dwelling on rejection, try to see it as an opportunity to move closer to finding the right match.

High Expectations: Many of us have high expectations for our potential partners. Our expectations are often fueled by societal pressures and unrealistic media portrayals. When reality doesn't align with these expectations, it can lead to disappointment.

Burnout: Dating apps and websites can be overwhelming. Swiping through countless profiles can become exhausting. Burnout is common and can make the process feel like a chore.

Past Experiences: Previous experiences that didn't go well can leave emotional scars. These scars can make it difficult to trust and open up to new people. If you're feeling way too nervous to date, consider talking to a therapist.

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How To Address Dating Discouragement

Practice Self-Compassion: Be kind to yourself. Understand that feeling discouraged is a natural part of dating. Acknowledge your feelings without judgment and remind yourself you're not alone.

Set Realistic Expectations: Focus on finding someone you enjoy being around. Embrace the imperfections and quirks that make people unique. If you enjoy someone most of the time, that's a winner.

Take Breaks When Needed: If dating becomes overwhelming, it's okay to take breaks. Step back, recharge, and return to the dating scene when you're in a better mindset.

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Lean on Support Systems: Talk to friends or a therapist about your feelings. They can provide valuable insights, encouragement, and sometimes even a fresh perspective.

Reflect on Past Lessons: Use dating experiences as opportunities for growth. Reflect on what you've learned about yourself and your preferences, and apply those lessons to future dates.

Stay Open-Minded: Sometimes the most unexpected connections can turn into fulfilling relationships. Stay open to meeting people who may not fit your initial criteria.

Focus on Self-Improvement: Invest time in self-improvement and personal growth. Engage in activities that bring you joy and boost your self-confidence.

Mix It Up: If dating apps aren't working for you, consider trying different ways to meet people. Join social groups, attend events, or take up hobbies that align with your interests.

Dating With Less Stress and Anxiety in San Francisco and Los Angeles

The journey to finding the right partner is unique for each person. By approaching dating with patience, adventure, and a positive mindset, you can make it a less stressful experience.

Dating doesn't have to be a source of stress and disappointment. By adopting a mindset that views it as a game, you'll shift your perspective and make it a fun and enriching journey. Embrace the One Date a Week Challenge, gamify your dating experience, and explore the beauty of your city along the way. Ultimately, it's about enjoying the process and creating memorable moments, no matter where the journey takes you.

Therapy for Couples and Holistic Therapy in California


Ready to navigate the complexities of dating with less stress and anxiety? Schedule a therapy consultation today and embark on a journey of self-discovery and personal growth. Our therapists provide compassionate support and guidance to help you navigate the world of dating with confidence and resilience. Take the first step towards a more fulfilling dating experience by booking your consultation now.

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