My son, 14, is close friends with two schoolmates who are brothers (one also 14, the other 13). Their mother has a somewhat forceful personality, but we’re on generally easy terms - e.g., our boys will sometimes have a sleepover or just hang out together at her place or mine.

Recently, this mother offered to take my son on a 10-day Florida vacation with her, before school starts again.

My son begged me to say “Yes.” I did. Many unexpected issues then arose.

I learned that they’d all be sleeping at the home of one of her relatives, but the boys had to stay out all day. All their activities were already pre-arranged.

They were thrilled. But I was not. Though I’m single (divorced) and would love 10 days to myself, the sudden revelation that I’m expected to pay for my son’s share of everything, wasn’t mentioned until after the plane tickets had been bought ahead by this woman.

She’s informed me that I’m also to pay for my son’s three daily meals, a share of the already-secured boat rental, one-third of the cost of pre-arranged sports activities, plus a portion of car rental costs and money for gas!

I was stunned, especially when told that my share had to be paid upfront.

Of course, I’d comfortably assumed that I’d pay my son’s air fare, and give him money to buy his own casual meals when out with his pals. I’d also intended to buy their mother a gift to express my appreciation for this rare travel opportunity for my son.

But here’s my confused thinking:

1) The trip’s already been planned; 2) Crossing this stressed, intense mother could be problematic for me, and for my son’s friendships with her boys; 3) I’ve learned of tension between the woman and her Florida family: The relatives don’t want the kids hanging around the house.

Should I send my son off with this mother?

Awkward Situation

Given the costs, you could instead take him on a vacation yourself! But, that’s not the same as what he’s been pumped up to expect.

The other mother has proven problematic. You must decide whether she can be trusted to keep her sons and yours, safe.

Many parents would’ve bowed out of this plan immediately, even if they could afford it. Talk to your son (and his father too if you’re sharing custody).

Tell your son that the activity plans sound fun, but there doesn’t seem to be time for just relaxing as you three normally do at your own homes.

Watch his reaction closely. You know your son best, and whether he can handle this full itinerary. The final decision is yours.

My cousin, 28, is a small-town social climber, obsessed with getting invited to parties where “important” people gather. It’s silly because she thinks the annual summer ball at the local sailing club is the event of the year (she’s not a member).

I like my cousin but feel I should tell her that her social-climbing efforts are obvious. Some people are laughing at her. I’m considering telling her that she’s making a fool of herself.

Small-town Ambition

Don’t dismiss your cousin’s pride. She does no harm by yearning for what she interprets as status and respect. Cliques are common in small communities, and not as important as she imagines.

She’s really seeking her own sense of achievement. Encourage her to pursue this, and she’ll grow confident.

FEEDBACK Regarding the tuition donors whose niece isn’t working (July 18):

Reader – “They should change the financial arrangement by offering to match (if possible) whatever amount their niece saves by working. If she blows any earnings on frivolities, she still won’t have learned important lessons about being an adult.

“However, they need to trust her parents to not put money in her account temporarily, so that they get out of paying her tuition.

“Or, change the offer to a reward trip abroad when she graduates.”

Reader No. 2 – “It’s funny how, as soon as relatives generously give someone a gift of money, they think they’re buying permission to comment on the recipient’s personal choices.

“They’d initially offered the money without conditions. So, it’s not fair to add them afterwards.

“Was the money given to help the niece or to gratify their egos? They won’t look very generous if they start adding conditions on paying up.”