Ask Amy: Generous couple wants to leave huge tip

Dear Amy: 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

Dear Diners: 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.

Dear Amy: I’m wondering if you are familiar with marriage retreats that supposedly offer a concentrated three-day format to immerse and attack all issues affecting a poor marriage.

These can be very expensive, ranging from $4,000 to $12,000 — not including transportation, lodging, and meals.

Are they worth it?

Do you have any experience or recommendations?

— Curious

Dear Curious: I don’t have any personal experience with marriage retreats (or “relationship intensives,” as they are sometimes called).

I don’t see a big downside to leaving one’s home in order to concentrate fully on a relationship, although I do believe that a lot of wisdom can also be gleaned by intentionally spending time with couples who have successful long-term relationships, and by learning the various ways they negotiate their way toward solutions.

I believe the main utility of a marriage retreat might actually be that the decision to attend a marriage retreat together helps to demonstrate to each spouse that their partner has a commitment to trying to improve the relationship. Then, when you are in proximity to other similarly committed couples being guided through various communication exercises, the atmosphere can become one of healing and change.

If this works longer term, obviously it would be extremely valuable. Learning to communicate in a new way can completely change a relationship.

If you can afford to try one of these retreats, research it completely before you commit to going. Going into debt to attend an expensive workshop would only amplify your problems.

Attending marriage counseling over the longer term can also be useful, and if you haven’t tried that yet, it might be a good place to start.

Dear Amy: “Loving Husband’s” wife wanted to start a new business. He mentions that among his wife’s many strong attributes, “being a natural entrepreneur is not one of them.”

I believe the couple would benefit from the free assistance of their local SCORE chapter.

SCORE (score.org) is a resource partner of the U.S. Small Business Administration (SBA) with the nation’s largest network of volunteer, expert business mentors.

— SCORE Mentor

Dear Mentor: During this period of economic and personal “churn,” the help and advice offered by SCORE is invaluable.

Seekers can be paired with volunteer mentors by entering their ZIP code on the website.

Kudos for what you and other volunteer mentors do for budding entrepreneurs.

(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)

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