Love At First Pitch: Dating Advice For the Fervent Fundraiser

by Joan Garry

Are you all ready for your year end fundraising? Want some advice? Check out my podcast episode with Gail Perry around successful year end fundraising.

A member of my team, Amy, recently thanked me for my dating advice.

Me? Dating advice?

I mean, I wasn’t the dating sort of person. Likely, some of that was a function of being totally clueless about my sexual orientation for a long time. Honestly, I went on precious few dates.

That said, one of those previous few dates has lasted over 40 years. Maybe I should be in the dating advice hall of fame!

Probably not. But in all seriousness, I had never given Amy dating advice. So what was she talking about?

She explained. Amy was working one day, captioning a masterclass for our Nonprofit Leadership Lab called “The Perfect Fundraising Lunch” and she realized that it was chock full of advice she could use for an upcoming first date.

I immediately wanted to know two things…

  1. What was the dating advice?
  2. Did she get a second date???

Let’s find out, shall we?


1. Be intentional about the location. I encourage fervent fundraisers to make a very intentional choice about where to have lunch. It doesn’t have to be the nicest place, but it has to meet certain criteria:

  • Quiet, but not too quiet
    This will be a conversation and you both need to hear every word. Too quiet? No one else there? That means you picked a restaurant no one goes to and the silence will feel really awkward.
  • You can make a reservation
    Waiting for a table is time lost and makes everyone super nervous. You end up talking about how long the wait will be or investigating tables from afar – “Oh, I think that table just got their check.” Not exactly an exhilarating conversation.  

    By the way, this is the problem with meeting for coffee, too. How do you deal with who orders, how long do you have to wait to order, for pickup? Just too many variables.
  • Diverse menu
    You just want to avoid pre-conversation that is wildly uninteresting. If I have a limited number of questions to ask before the lunch date I really don’t want to squander one on learning whether my lunch date has peanut allergies.

2. Pre-select your order. This is one of my most important pieces of advice (which is why pre-selecting the location is key). The most decisive people I know get ridiculous looking at a menu. And in these situations  – date or fundraising – you are meeting someone for the first time and you want to be self-assured, right?  

Instead, you stare at the menu, frozen and you ask that absurd question that is asked endlessly at lunches: “So what are you having?”

So much wrong here.

First, do you really want to come across as so indecisive that you are asking a total stranger what they are having? Next, why does it matter what they are having? And third, you begin to play what I call “menu ping pong,” and that is just the worst – a total waste of time and unflattering to both of you.  

“So what are YOU having?”

“I haven’t decided. How about YOU?”

“I’m trying to decide between the Caesar salad and the calves liver.”

“Oh! Calves liver! That’s interesting (no, it isn’t really). Do you think the shrimp is good here?”

“I don’t know, I’ve never tried the shrimp here but it’s delicious at X restaurant across town. Actually, I’ve not had the calves liver here either. Do you think I should just get the salad?”

“X is a really nice place- I’ve never had shrimp there. I’ll have to try it. But I don’t see shrimp on the menu.”

“Oh, I’m sorry.”

I annoyed myself just writing that. You have limited time (maybe 50 minutes of legit time) to begin to build a relationship, to see if there is a good fit and you’re going to waste 5-10 mins on ordering? NOOOOOOOOOOO!!!!

So, go to the menu the night before and pick. I think you can’t go wrong with a chicken Caesar. Then you can stop worrying and be decisive at lunch.

Three other quick points:

  1. Don’t tell the person you pre-selected. That could land as weird. Some things people just don’t need to know.
  2. Don’t order anything that requires slurping.
  3. Avoid spinach or worse yet, seaweed salad. Even if stuff is not caught in your teeth, you will think it is and you won’t be your full self at lunch. And it will be nearly impossible for your lunch date not to stare at it. 

3. Ask an open-ended question. The one I like is, “Tell me about who you are.” It gives the lunch date an opportunity to take the question in all sorts of different ways – I might learn what they care about, who they care about, their interests, their personality. 

You have a chance to learn about the person and hear about what matters to them – and determine if it aligns with what matters to you.

4. Plan ahead about how you would answer that same question. What do you want your lunch date to know about you (or in the case of a fundraising lunch, you and the work of your organization)?  

In either case, give some thought ahead of time to the stories you want to tell. Is there a story you can organically weave into the conversation that helps the “date” understand you to determine if they want this to be the last date or the first date.  

And same with a fundraising lunch – make sure you have 2 or 3 stories at the ready that really bring the work of your organization to life. Select the story that you think will really connect with the person you are getting to know.

5. Would you like to keep the conversation going? Now it’s possible that as a fundraiser you are going to lead to a specific ask for a contribution. I can speak from experience that this is part of the art of fundraising. You actually can ask for a gift at that first lunch if it feels right and I have on many occasions.  

But in most situations, your goal is to get another meeting. And so a question like, “Would you like to keep the conversation going” is a great way to secure permission for another time to meet. 

Unless, of course, you determine there is no fit between this person and the work of your organization. Remember fervent fundraiser… it’s just like a first date.

First, you have to figure out if you want to keep the conversation going. If you do, a question like, “Would you like to keep the conversation going,” might feel softer and easier. And you will be able to tell from tone and nonverbals if “yes” really means yes.


I’m sure you’re wondering if, armed with my expert-level dating advice, Amy got a second date. I sure was!

First, here’s an important bonus piece of advice that Amy felt was important for me to share. Be positive and enthusiastic – it’s contagious!! You want your lunch date to enjoy your time together regardless of what happens next.

Ok… about Amy’s date…

Well, she actually secured a $25,000 gift for a local charity!

No. That was a joke.

She followed steps 1 through 5 and brought her very sunny disposition. She ordered a Caesar with grilled chicken. As far as she knew, no food landed in her lap or between her teeth. She was really happy she gave thought to stories she might want to tell and her date loved the open-ended question, “tell me about who you are.”

I guess they both liked what they heard.  They both decided they wanted to know more and there was indeed a second date!

Is there a moral to this story? Oh you bet.

Fervent fundraising is about being intentional and about building relationships – it doesn’t get simpler than that.

P.S. As for my own first date with my wife, it didn’t go anything like this. And that’s all you’re getting from me.