Don’t Propose on the First Date

Imagine being on a first date and getting a marriage proposal.  Does it happen? Sure. We’ve all seen Frozen. Does it all work out well? Signs point to no, it doesn’t always work out well. In all seriousness, most of us would be shocked, taken aback, and probably a little scared.  

Yet, that’s exactly how we sometimes treat donors. We’re so excited to connect with a new donor that we roll out every option at once: Call me anytime. Come for a tour. Meet our president. Let me tell you about all sixteen programs. 

Those are all good things. But it’s too much, too fast.   

What if instead, we took a gentler path? What if we treated a new donor relationship the same way we treat a new personal relationship? Kara and I are fans of the dating analogy when we talk about stewarding donors kindly and intentionally. 

The first call: getting their digits. 

Getting someone to give you their name and number used to be a big deal (“You like apples? How about these apples?” Apparently, we’re doing movie references today). On that first call, it’s a win when the donor says, Sure, you can call me again or Feel free to send me an email. That’s enough.   

Will some donors volunteer more? Sure. But if they don’t, that’s okay.  There’s room for the relationship to grow. 

Subsequent calls: the dating dance. 

On the first few dates, most of us don’t dive into childhood trauma and past relationship history. We keep it light. We find common ground: family, interests, work, experiences, things we enjoy. Unless you’re Kara – then things get real when you give your future husband a sleeping pill on the first date. (There’s a great story- but that’s for another time). 

Donor conversations can work the same way. You don’t need to uncover every little thing about them.  One or two nuggets is enough. Maybe you start by understanding what drew them to your organization. Maybe you ask about the causes they care about generally. Maybe they mention family or work, and you ask a thoughtful follow-up question. This is especially powerful when you’re using permission-based questions. 

Curiosity works better than interrogation. 

Moving the relationship forward. 

Over time, the information you gather may create an opportunity to go deeper. 

Just like dating, there comes a point when trust has been built and the relationship naturally moves forward. There is room to learn more, share more, and deepen connection. 

With a donor, this might look like affirming what you’ve heard and asking whether they would be interested in engaging more deeply. Maybe that’s a tour. Maybe it’s meeting the staff. Maybe, eventually, it’s reviewing a proposal. 

The key word here is eventually. 

What this looks like in real life 

There’s a reason we use this analogy and feel strongly about taking things slowly. We’ve been on too many calls with fundraisers eager to tell us about a conversation with a new donor. If you can imagine a breathless, enthusiastic voice, it sounds something like this:  

"Oh, they were lovely! I told them I’d be their contact and update them regularly. They can call me anytime with questions. I asked what they care about and told them about our sixteen new programs, invited them to next week’s event, and offered to set up time with our CEO." 

Friend, we are exhausted just hearing the recap. 

More importantly, if we put ourselves in the donor’s shoes, we know exactly how we would feel: like someone on a first date getting a marriage proposal (or a sleeping pill). Overwhelmed. Pressured. Maybe even ready to run. And what happens when we ask about that donor later? 

You probably guessed it. They stop answering calls. Emails go quiet. What felt warm suddenly feels distant. 

Instead, imagine hearing this: 

"They were great. I learned they prefer email. They said they care deeply about the mission, so I told them I’d send occasional stories and updates. My next step is to share a story about Program X and, over time, learn which parts of the mission resonate most." 

That’s relationship building. 

When we slow down, listen well, and ask thoughtful questions, donors begin to trust us. The information we share feels relevant because it’s grounded in what matters to them. Relationships grow best when we stop trying to fast-forward them.  

And in fundraising, just like dating, moving too fast rarely ends with a ring.