July 27, 2011
HOOTERS CASINO BLUES
My best friend of more than twenty years and I decided to have a boys’ long weekend in Vegas just for laughs before we get any further into our middle age. The problem is, my best friend insisted on making the arrangements and has gone and booked a single room (at Hooter’s Casino, no less) with a package that has connecting flights stopping at every state capitol between Vegas and home because he wanted to save money. This is a guy who makes six figures. Twenty years ago I wouldn’t have balked, as I would expect no less than to share a room with my best buddy filled with pizza boxes, beer bottles, and overflowing ashtrays. However, we are now men in our early forties who make very good money, and I have no desire to share a room so I can watch him belch in his underwear, nor do I want to spend twelve hours getting home when it normally takes a quarter of that time. I would also like to stay at a decent casino as opposed to some backdrop from “My Name is Earl.” My question is, how should I go about telling my best friend to stop being such a cheapskate and spend some of that moolah he worked so hard for without hurting his feelings? He takes a lot of pride in being frugal. My wife thinks I should just come out and tell him. Is she right? Or should I just suck it up and go through with it?
—Not a Middle-Age Miser in ???
Dear Not a Middle-Age Miser,
If you care anything about keeping this friend, you have to tell him the truth and object to the weekend plans. If you try to just suck up and endure that kind of Trip From Hell, chances are your friendship will end before your tour of state-capitol airport cocktail lounges comes to an end. Tell him exactly what you think: “Stop being a cheapskate and spend some of the moolah for which you work so hard.” Show him all the nice casinos on the Internet with beautiful rooms and luxurious amenities. Talk about the sweet benefits of being alone in his own room—no wife, no kids, no dog—to do just as he pleases, master of his universe. If he can at least buckle in on the living conditions, maybe next year you can get him to try spending a bit more on travel plans. If you can convince him to just try it once, he will never look back and will probably be laughing that he ever dreamed up such a hideous trip.
LOWBALLING HOW MANY YOU’VE BALLED
I have been dating a man for about three months now. He asked me what my “number” was, as in the number of men I have slept with. I told him I was not going to tell him, and this caused a problem. Do you think I should tell him?
—Should I Tell in Telluride
Dear Should I Tell in Telluride,
No. Under no circumstances should you tell him your real number—a random lowball number yes, but an accurate number? NO! For God’s sake, NO! You will be safe if you hover around six, but don’t dare flit above ten! No man wants to think they are dating or possibly thinking about marrying and having children with the city slut. It does not even matter if the number is believable. If you repeat it enough, they will believe you because they will want to believe you. If you think, “It is unhealthy to start a relationship based on a lie, whaa whaa whaa,” grow up and ask yourself: Is it better to have a relationship based on a lie or no relationship at all? And just in case you were wondering, it is a good policy to not discuss or point out old crushes, hookups, or boyfriends, even if they are sitting right next to you at dinner. The less he knows about your sexual past, the better. Trust me: Neither of you want him to have visuals of your sex history. So purge most of that history—one by one, erase the notches on your lipstick case. This is definitely a situation where you don’t want to look like a battle-scarred war veteran covered in medals.
MY BROTHER THE COCKBLOCKER
I am a 39-year-old man who has never been married, and I am finally dating a girl that I really think could be the one. My problem is my brother, whose opinion I really respect. He already has a successful marriage and two great children that I love spending a lot of time with. But he is telling me she is leading me on and that she will never take me seriously and I should walk away now before I get hurt. I love and trust my brother, but I really think he is wrong. We have been dating for about a year and I really have no idea where he is getting the idea she is not really into me, even when he tries to explain it with examples of comments he has heard her make. He is like a dog with a bone and just will not stop nagging me to get out now.
—Protesting Brother in Toronto
Dear Protesting Brother in Toronto,
There could be a few reasons your brother is behaving like this: 1. Your brother knows something about this girl that you don’t—something damaging that he doesn’t want to tell you directly, such as he slept with her on multiple occasions while you were dating, or she has a criminal record for trafficking children. 2. He is a little bit jealous and afraid of losing you as part of his own family circle. The minute you have a wife and children of your own, he is not going to be able to depend on you as much as he does now. Nobody with children ever really wants to have to share or outright lose the friendly and helpful uncle. 3. He is simply a disagreeable SOB. 4. He loves you and is being over-protective and you are going to have to muddle through. However, when somebody that close to you has alarm bells going off, it is always a good policy to do a little investigating and not stick your head in the sand like a panicky ostrich.
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