07/30/2013 12:02 pm ET Updated Sep 29, 2013

Ask Michael Cohen: How to Share

My friend and I took a time share on Fire Island. We are besties and not only do we like the same things but we like the same guy who also has a share at the house. My friend can't stop talking about how amazing he is and about the bulge in his speedos. I haven't told my friend how much I like him. I think the guy knows something is up. What would you do? Step aside or go for it? -- Shane W., New York City

Can you please stop using the word 'besties?' You sound like a 16-year-old girl who actually has no 'besties.' Anyway, you have two choices here: confess to your friend you have a crush on him too or pass. I tend to question how serious a Fire Island crush can really be. This really sounds like a battle of the bulge, ahem, so may the best man win or maybe it will be a tie and you know where I'm going with that.

I think my fiancé's sister is a bitch and I can't stand seeing her every weekend in the Hamptons where we rent a home. She is constantly telling me how great she thinks her brother is and what a lucky girl I am. Can you believe the nerve? She is also always trying to one-up me on everything. I find listening to her dating stories and how no guy is good enough for her intolerable. My fiancé doesn't say anything because he doesn't want to get involved and I really don't want to push it too hard. How would you handle the rest of the summer? -- Name Withheld, New York City

I'd drown the bitch in the pool, that's how I'd handle the rest of the summer. Seriously, though, you have a much bigger problem on your hands. She's going to be family so think of this summer as your dress rehearsal. When I don't fancy someone, I ignore the hell out of them. If you engage in her crazies, you're only going to egg her on and you'll be bright red, not from the sun, but your frustrations. Eventually, she'll get tired of telling you how great her brother is and her tedious dating stories. As for your fiancé, he's going to need to man up and let his sister know she's a bit much. However, before you're married there is no need to rock the boat. You certainly will have to follow through with him after the wedding so that he lets his sister know she can't speak to his wife like that.

My husband and I rented a summer place in Provincetown and we have not had the time to use it as much as we would have liked. I thought it would be a good opportunity to share it with my friends. We really don't hurt for money but my husband thinks if they want to use the house, they should pay for the weekends. I don't agree. Thoughts? -- Lilly F., Boston

I think your husband is cheap. All that aside, you really can't turn on him and tell your friends that you aren't siding with your man on this one. I am sure your friends will question the situation and I can't blame them -- it's strange. Try going up with a couple of your friends, sans hubby, for a weekend or two -- that way he won't want payment as they are your guests and won't be irked that the house is occupied by your friends only. For the unlucky few that don't get to go, maybe they can call the 'besties' on Fire Island.

I'm single, but one of the friends I took a summer share with is a stepmom to four girls. When she doesn't come down for a weekend, she lets the 19-year-old and her girlfriends stay at the house. They are New York City spoiled brats that think the world, and this house, revolves around them. They are loud, leave a mess wherever they go and incessantly play Justin Bieber. I can't take it. They are ruining my weekends. Help! -- Melanie S., New York City

I'm not sure what's worse -- the mess they make or listening to Justin Bieber. Straight up, you need to call this stepmother of four and ask her "What the what?" Simply tell her you rented the house with her and as much as you love the girls, and I'd stress that, it's not turning out to be the calm and relaxing summer share you had hoped for. She may counter this with she'll tell the brats to behave better. It also wouldn't hurt if someone else in the house felt the same way you did and all of you stood together on this.

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