Actress Alyssa Milano Asks For Money For Her Son's Team—Are Fundraisers Awkward or Okay?

Like many of you, I saw the headlines when actress Alyssa Milano appealed to the masses for donations to her 12-year-old’s sport. In case you missed it, last week, the former Charmed star posted this on X: “My son’s baseball team is raising money for their Cooperstown trip. Any amount would be so greatly appreciated. You can read more about the team and make a donation here.” From there, Milano shared a link to a GoFundMe page, with the goal of raising $10,000.

Many of us balked because her net worth has been reported as being somewhere between $4 and $10 million. Does she have Reese Witherspoon money? No, but the Who’s The Boss alum lives better than most of us can imagine—and has access to things and people mere mortals do not. 

After Milano attempted to crowdfund her son’s baseball trip, I promptly moved on with my life, forgetting about the incident—although admittedly, it put a brief, bad taste in my mouth. I did see a blip about how she was under so much fire, that the actress soon took to X again to defend herself.

In a subsequent post, Milano said, “I’m getting media inquiries about whether I have financially contributed to my son’s baseball team. I’ve paid for uniforms for the entire team and coaches, thrown birthday parties, and sponsor[ed] any kid who can’t afford monthly dues. The kids also do fundraising themselves—car washes, movie nights, and many other fun things!” She finished the post by thanking the many folks who contributed to the GoFundMe. And, at the time of writing, the effort had raised over $11,000.

Flash forward a few days, and Milano’s solicitation scandal became front and center for me when my kindergartener brought home a fundraising flier from his school. I immediately felt a sense of ick overwhelm me. Now first and foremost, of course, I recognize that supporting our school is extremely important, and I will have no problem writing my own check for this drive.

But appealing to friends, family members, and neighbors who have their own expenses, and causes that matter to them—many with kids with fundraisers of their own—is just about as awkward as it gets.

Let’s start with the fact that Americans are suffering in the current financial climate. Add to that how there’s a cause that needs your support everywhere you go, from a cheerleading squad with a table set up outside of the market, to a prompt to round up your total each time you purchase a product from a store. It’s easy to get overwhelmed—without me and my kid knocking on your door to demand a donation to a school fundraiser every few months (In the fall there was another similar initiative that made me cringe.)

These types of fundraisers are especially dodgy for other reasons, including that the prizes kids can earn when they reach certain goals are literally a joke. For instance, if my son were to raise $250, he would get socks...socks!

Beyond the underwhelming rewards, we aren’t offering anything to a potential benefactor. For instance, I talked to a co-worker who considers herself to be a “fundraising parent,” and learned that to raise money for pricey competitions, her daughter’s dance team sells pies at Thanksgiving, poinsettias around the holidays, and Super Bowl boxes during football season—just to name a few fundraisers. I would much rather have a good or service to peddle to my parents, aunts, uncles, friends, and neighbors than simply ask them to fill out a donation sheet. Sure, they get to feel good about supporting a good cause, but…

Given how disinclined I am to badger anyone for money this soon after we all practically went broke this Christmas, I’m back to wondering how Milano got up the nerve.

Even my co-worker acknowledged it’s an awkward position to ask anyone for money or to buy something to benefit her kid. As she views it, fundraising for kids’ sports is a necessary evil given the high costs often associated with higher levels of competition. She said they wouldn't be able to afford her daughter's dance without the fundraising. Maybe the same can be said for school fundraisers. But I’m still having a tough time, and even more so because I can’t so much as offer cookies to folks willing to support us. 

The good news is that for every fuddy-duddy like myself who can’t seem to get on board with crowdfunding kids’ lives, there are twice as many generous, kind-hearted individuals willing to give a little—or a lot—toward schools, sports, and charities. And, there are “fundraising parents” who put their pride aside and work toward the greater good of making their children’s dreams a reality.

I suppose that’s what Milano was doing, but come on—couldn’t she just have asked a few Hollywood bigwigs and left us out of it? Oh, and by the way, Alyssa, if you’re reading this, any interest in donating to my child’s school?