Frequent Diners

My husband and I usually have breakfast several times a week at a local coffee shop.

Over the years, we have become friendly with several of the waitresses.

At this time, there are two women that we would like to give special financial gifts to. One is a single mom whose daughter is a straight-A student and needs money for a school trip to Washington, D.C.; the other one is putting herself through nursing school while working as a waitress and just passed her nursing exam.

Both of these ladies are hardworking, lovely people.

We would like to give them each a financial gift of about $500, but my husband is afraid that if we do, the word will get around to the other employees at the coffee shop and we will make ourselves targets for anyone who needs money. We can’t do this for everyone. How can we handle giving these two gifts without making ourselves look like “soft touches” for anyone else who needs money? We need your help on this one. Frequent Diners

I love Amy’s reply, and share it with you in entirety -” I love your instincts, but I wonder if your worry is misplaced. The biggest hazard here might be that the recipients of your generosity would feel awkward accepting, which would affect the dynamic at your favorite spot.

If you have developed a personal connection with these women, you can approach them and ask for their home address so you can send them a card.

For the first recipient, you can enclose a note saying that you would like to sponsor her daughter’s school trip to Washington. For the second, say that you would like to congratulate her on her hard work and that you hope your gift helps to defray some of her school costs.

In your notes, say, “We hope you will keep this gift private. We only ask that someday, if you have the opportunity, you might pay it forward to someone else.”

There are also ways to give anonymously (do an internet search).

Anonymous giving is a high-caliber form of generosity, and would also help you to continue to drink your coffee at your favorite spot, knowing that you are a most virtuous tipper.

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2 Responses to Frequent Diners

  1. adguru101 says:

    Unfortunately, being generous can sometimes make the recipient feel awkward, embarrassed or resentful. They might consider a smaller amount ($50-100 each?) as a thank-you at the holidays rather than earmarking it for a specific event. The women can then use the money as they choose.

    Liked by 1 person

    • msw blog says:

      Great suggestion about gifting at the holidays. I reread this query, and I would not ask them for their home address. That is boundary crossing. I would suggest they dole the sum out over time perhaps a ” $20 “tipper visit, as they mention they frequent several times. If the single mom has mentioned the name of her child school, they can outreach to the school directly and make an anonymous donation to the child’s trip. Regarding the waitress who passed her exam. I think they could leave a large sum, and a note on their receipt congratulating her and how they are going to miss her at the restaurant.

      Liked by 1 person

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