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  • Debra A. Gill

Don’t Propose on The First Date

Updated: Oct 14, 2021

Exploring the commonalities between fundraising and dating.



Most of us have been on more than a few dates in our lifetime. Some people are very good at the various stages of romance and others could use a bit of practice. Typically, dating involves meeting someone, exploring common ground, spending lots of quality time together, and, if the fit is right, a marriage proposal. Fundraising is very much the same and far less intimidating when you really dig into it.


Identification – You see someone on a hike, make eye contact, nod, and smile. Later you run into each other in the parking lot and strike up a conversation. Plans are made to meet for a hike at a different location the next day.

  • Your organization receives an annual fund contribution from a new donor.

Qualification – You spend the next afternoon hiking, talking, laughing, and mutually determining whether you have enough in common to move forward to a second date. Without getting too far into the weeds, you are curious enough to ask good questions and listen to the answers, noting items of interest.

  • You do a little research on the new donor and realize that they are quite philanthropic in your community and once attended an event organized by your not-for-profit. You pick up the phone and call the donor to thank them for their gift. During the conversation, you inquire as to what inspired the contribution. Based on the conversation, you invite them to meet for coffee and talk more about your organization.

Cultivation – Having jointly determined that you are interested in pursuing this possible connection, you begin dating. Now there is greater depth to the conversations. You explore common values, goals, ambitions, essentially determining if you are headed in the same direction. When you discover favorite foods, movies, sports, or music, you find ways to enjoy those together. You mutually invest time, energy, and creativity into building a lasting connection with the other person.

  • You discover that the donor has many interests that tie into your mission but has never toured or been invited to meet the leaders. A series of intentional conversations, tours, and interactions (aka moves) ensue over the coming months. Along the way, you explore how they make their giving decisions, how they like to be recognized, what inspires them to keep giving to their charities of choice, and what areas of need appeal to them personally.

Solicitation – When the time comes to take the partnership to a new level, it’s highly likely the decision has been given deep thought, maybe even been discussed in advance. A lot of preparation goes into the proposal, incorporating what has been learned during the courtship because the person proposing wants to make sure that the answer is yes!

  • After careful planning, you are ready to pop the question. You have the right solicitation team, the right approach, the right ask amount, and the right strategy. They say yes!

Stewardship - Anyone who has ever been married knows that once the “I do’s” are exchanged, the hard work is over, right? Not so much. The real work begins after the wedding. For the romance to endure, it must be thoughtfully nurtured with creative ideas that appeal to each partner and build toward a long-term stable relationship.

  • The gift is booked and after the appropriate appreciation is expressed, the cycle begins again by cultivating the connection and bringing the donor along, so they are inspired to grow their generosity and increase their impact.

While this correlation between fundraising and dating may be oversimplified, I find that it is effective in working with volunteers, and sometimes staff, to help alleviate the anxiety that comes with asking for money. Start at the beginning, build a trusting, authentic relationship, be intentional with the proposals, and the funds will follow. And by the way, in this analogy, the volunteers and board members are the ideal matchmakers. They can bring community members together with your missions in ways that could lead to powerful alliances for years to come.

Alliance Philanthropy’s philosophy is to inspire staff, volunteers, and board members for all types of not-for-profit organizations to raise funds enthusiastically and passionately - at maximum levels - in support of their missions.

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