Dear Melissa
I have a friend who, whenever we get together for dinners or outings (with or without the kids), always contributes less than her share. If we go out to dinner and the bill comes to $50, she'll only offer $20 to help with the bill, even though we have all indulged equally.  When we go to the amusement park, I always end up buying the tickets.  She either never pays me back or hands me less than what she really owes.
 
I am not a nickel-and-dime kind of woman and hate inconveniencing the wait-staff by asking for separate checks.  I feel uncomfortable pointing out that she hasn't contributed her share, but this happens literally every time we get together and I'm starting to feel as if she is taking advantage of me. How can I solve this problem?

Dear Fork It Over,
I hate to be the bearer of bad news, but….you are definitely being taken advantage of by this friend.  Women, especially moms, are blessed with the gift of remembering.  Remembering what time to pick up the kids, remembering exactly how much money they saved at the supermarket, remembering exactly what chores their husbands did not complete and remembering how much money they owe or are owed (often times, down to the penny).  She obviously hopes that you are one of those few women that have a faulty memory!  It is time you put your foot down (politely, of course). 
 
Here is the game plan…
 
First, when the bill arrives or the tickets are purchased, clearly and confidently say, “The total price is $40, would you like to give me $20 now, or should I remind you another time?”  If she asks you to remind her, simply say, “Sure, I will write it down when I get home and will remind you if you forget.”  And, most importantly, remind her if she doesn’t mention it or repay you within a couple of weeks.  After all, you’ll have many of years of never getting repaid when your teens borrow money, so you might as well save up while you can.
 
If she does offer less than she truly owes, tell her, “Oh, I’m sorry, I must have misspoken, the total was $50, so it is $25 each”.  Yes, there may be an awkward silence, but it is your friend that should feel uncomfortable, not you. 
 
Even though you feel uncomfortable asking for separate checks, it might just be the way to go…for now.  If the thought of doing this makes you cringe, you can discretely approach the maitre’d when you arrive and explain that you would like two separate checks.  If you think that you can say it in front of your friend, by all means, say, “Why don’t we get separate checks, as I may be indulging myself tonight and would hate to split the check when I have obviously ordered more than you.”
 
Lastly, here is my favorite way to handle this problem…only bring enough cash for your meal, your tickets, your fun!  DO NOT offer to use your credit card.  If she doesn’t have the cash, I am sure she has a credit card readily handy in her purse.  Once she sees that you aren’t paying, she can either give her share of the cash or hand over her credit card.  In the latter case, you can ask if she would like to put the whole bill on her card and you can give her your share in cash.