Date Planning Services

At Two Happy LLC, we believe that one of the key paths to thriving is having strong, nurturing relationships.

Science has pointed again and again to building strong relationships as the foundation to a life well-lived. We believe in giving your chosen life partner your best, rather than your emotional leftovers. Societal demands push many couples to take one another for granted, and we want to bring an end to that. We leverage the latest positive psychology research on how to flourish to help plan and execute logistics for your dedicated date time together each month.

We’ve seen high powered career couples spend over $300 per week for housekeeping services, $350+ per week for career coaching, and over $250 per week for couples counseling. These are wonderful services, but don’t directly invest in building the strength of your relationship with one another.

We understand how busy lives leave couples with little bandwidth to plan beautiful, curated dates. We understand how difficult it is to even make the time to go on the date, and to immerse yourself and enjoy it completely. Let us smooth the path ahead for you by taking on all the logistics and planning.

All packages are for date planning services only and do not cover the expenses of the date (i.e., you pay for event tickets, food, drinks, and any other additional expenses). Dates will be planned based on the budget you set during the introductory interview unless otherwise agreed upon by all parties. Dates typically last 3-6 hours including any travel time.

All subscription packages can be billed monthly, semi-annually, or annually. We recommend a minimum of a six-month package so couples can truly appreciate the changes in their relationship as they make high quality time together a regular part of their routine.

To purchase any package, simply use the “Contact Us” form and leave your name, email, phone number, and which package you’d like. A date concierge will contact you for next steps and send you an invoice. 

Two Happy Packages

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Six-month Packages: $120

Six dates fully planned for you and your partner based on your chosen theme. 

Choose from the following themes:

  • Iconic Chicago
  • Chicago Culture & Museums
  • Foodie Chicago
  • Nightlife Chicago
  • Romantic Chicago
  • Outdoor Chicago

To purchase, simply use the “Contact Us” form and leave your name, email, phone number, and which theme you’d like. A date concierge will contact you for next steps and send you an invoice. 

person balancing rocks

Luxury Package: from $199 per month

Choose 1 date to enjoy from 2 fully custom ideas delivered monthly. Add additional dates for $50 per date.


    • 45-minute onboarding interview to discuss detailed preferences
    • One fully planned day trip per year upon request (8-14 hour date)
    • One fully planned overnight weekend trip per year upon request (up to 3 overnights)
    • Unlimited gift ideas and gift planning for birthdays, anniversaries, and holidays for you to give one another
    • Annual measurement of Relationship Satisfaction
    • Customer support to troubleshoot dates
    • Three 45-minute meetings each year with your dedicated date planner that includes date planning check-in as well as 20-minute mini positive psychology workshops covering a range of relationship-building skills for communication, thinking traps, capitalization, resilience training, and more!

    To purchase, simply use the “Contact Us” form and leave your name, email, phone number, and let us know you’d like the luxury package. A date concierge will contact you for next steps and send you an invoice. 

    woman in black long sleeve shirt sitting on blue and white checkered table cloth

    À la carte pricing

     Includes planning and logistics. You show up and have fun. 

    • $60 per date night (3-6 hours)

    • $100 per day trip (8-14 hours)

    • $150 per day for overnight trips.

    To purchase, simply use the “Contact Us” form and leave your name, email, phone number, and which service you’d like. A date concierge will contact you for next steps and send you an invoice. 


    Two Happy LLC offers positive psychology couples skills’ workshops. These are 90-120 minute long private classes with the couple, led by an expert in positive psychology. While each workshop is different, all have a learning component, multiple interactive hands-on practice, and continued learning booster home activities. To purchase, simply use the “Contact Us” form and leave your name, email, phone number, and which workshops you’d like. Your workshop facilitator will contact you for scheduling and send you an invoice. 

    One workshop:

    $500 per couple

    Two workshops:

    $450 per workshop per couple

    Three or more workshops:

    $400 per workshop per couple

    Currently Available Workshop Topics:

    Active Constructive Responding

    Couples will learn about recognizing bids for attention, and the best way to respond to build upward spirals in the relationship. Couples will practice recognizing and using all four basic response methods, with emphasis on gaining skills for active constructive responding (Lambert et al, 2013).

    Emotional and Invisible Support

    Couples will learn about effective methods of emotional and social support, including invisible support (Girme et al, 2018) when their partner is going through stressful times, a crisis, or just needs some extra love.

    Resilience Training

    Resilience is the process of bouncing back (or better) after significant adversity or risk (Masten, Cutuli, Herbers, & Reed, 2009). It can also be used to aid in responding to everyday stressors. In this workshop, couples identify primary stressors in their lives, and learn about the 8 protective factors. Couples then use this to build and strengthen their protective factors.

    Overcoming Thinking Traps

    Our minds think incredibly fast—to do so, it has developed shortcuts to help us. A lot of times, these shortcuts are helpful, such as when something is falling, we intuitively might jump away before processing what is happening. Sometimes, these shortcuts hurt us in the form of thinking traps (Reivich & Shatté, 2002). In this workshop, we cover 8 common thinking traps (blaming only yourself, tunnel vision, magnifying and minimizing, etc.) and how to overcome them.

    Household Division of Labor and Habit-Forming

    Couples split immense loads from various aspects of their life, ranging from economic labor, childcare, household duties, and even social duties. How households split their labor is directly correlated with satisfaction with the relationship and with overall well-being (Ciciolla & Luthar, 2019). This workshop helps create a framework to discuss ownership of various duties, and uses the latest in habit creation and maintenance (Oettingen & Gollwitzer, 2017) to create a system that works for the couple.

    Rituals for Two

    Rituals range from the mundane (morning routine) to the meaningful (family dinner). Regardless of the type of ritual, the increased use of rituals predicts perceived increases in relationship quality and intimacy (Pearson, Child, & Carmon, 2010). This workshop helps couples recognize and increase meaning in rituals they already engage in, as well as help create new rituals for the couple to incorporate into their lives in a practical and doable way.

    Character Strengths

    Couples will individually take the VIA Character Strengths quiz to discover their character strengths. Strengths are interdependent, positive, and can lead to good outcomes such as happiness, achievement, better physical health, and stronger relationships (Niemiec, 2018). In fact, while the majority of people are unaware of their strengths, studies show that people who use their strengths are eighteen times more likely to be flourishing. We delve into strengths, recognizing and affirming one another’s strengths, and how to use strengths in new ways.

    More (Contact us for specific requests)

    Positive psychology and relationship science cover a number of topics. Contact us if there’s a topic you’d like to explore, or skill you’d like to develop as a couple for a custom workshop.




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