We ❤ our partners.


Matchmaker Caitlin D’Aprano

Stay updated with matchmaking events by joining Caitlin’s List for potential matches, events, and other news.

If you would like to hire Caitlin as your matchmaker, you can fill in her Client Application Form and she will get in touch to set up a time to chat. 

Join Caitlin’s Matchbook to have the opportunity to be matched with her clients.

Caitlin works with only a small amount of clients so that they can be her sole focus. Caitlin enjoys the relationship she develops with clients, helping them figure out what they’re looking for and makes herself available to them at all times. Hiring Caitlin as your matchmaker saves time, energy, cuts out online dating and is for people who are ready to meet their person, but don’t have the time or inclination to screen people, need support, accountability and/or dating advice.

Client Testimonials
Caitlin, I can’t believe how fun it has been to meet people through you. Your screening women for me has saved me so much time and energy. Your insight and feedback are extremely valuable. ~ Tyler

Caitlin is professional and thoughtful on her match search. The guys met all my priorities and also challenged my conditioning and prejudices. She helps me to know more about myself. I like her very much. ~ Katia

Caitlin looks forward to hearing from you!

Second Dates

Sidewalk Tastes takes you on a second date!

Did you connect with someone at a Piña Colada group dinner date? Take them on a second date 1:1! We have partnered with Sidewalk Tastes to make your date planning easy. Sidewalk Tastes are app-guided food tours through your favorite San Francisco neighborhoods. You’ll be guided point-to-point while tasting the city’s finest flavors without having to pull out your wallet. Simply show the app to receive your Taste. The app navigates you point-to-point and pairs cultural context with insights on your Tastes. You can go at your own pace and take any detours you like – you have all weekend to enjoy your Taste. You can sign up and explore the Piña Colada Sidewalk Taste tours here.

Restaurant Partners

We are proud to partner with Commonwealth. Executive Chef Jason Fox’s progressive Californian cuisine harmoniously combines flavor palettes from around the world, and a broad range of techniques to create food that is refined, distinctive and satisfying. You will enjoy a sparkling welcome drink and continue with an incredible multi-course meal that is doing good things for the community. Part of the proceeds will be donated to a different local cause each month.  Learn more about the Commonwealth’s exciting and adventurous dining in this portrait.

The Perennial, founded by the husband-and-wife team Karen & Anthony, was our first restaurant partner. Unfortunately, the Mid Market restaurant closed on February 9, 2019, after three years. The owners continue to work on their mission to address climate change with delicious food with their non-profit organization The Perennial Farming Initiative.


Todd Westphal

Todd Westphal is a commercial lifestyle, portrait and on-set photographer based in LA, SF, and NYC. Originally from the East Coast, Todd shoots for magazines, nonprofits, ad agencies, and production companies. He loves shooting portraiture and is keen on capturing people at their most true to self, whether David Beckham or a three-year-old toddler. He is excited about the prospect of helping you put your best face forward.


Six Degrees

Six Degrees is a monthly membership for every woman looking to build strong connections and life-enhancing experiences in her city. Whether you’re seeking a job, looking for a roommate, or launching a business – Six Degrees’ events, resources, and connections let you build the network, opportunities, and friendships you’re looking for to deepen and grow your life.

Six Degrees helps its tribe of dreamers and doers stretch their skills, challenge their minds and stir their creativity with out of the box programming. Events range from expert panels, 101 events, and hands-on workshops. Every gathering includes speed networking.

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