Earth to Young Hottie: Don’t sleep with your boss!
Welcome back!
When you sleep with your married boss you run the risk of….
- Alienating yourself from your coworkers (Trust me, they know what’s going on.)
- Losing clients (They also know what’s going on.)
- Getting caught by their spouse (Guess what, you’ll lose this battle.)
- Getting fired (Exactly how you will lose the battle.)
- Getting knocked up (Your child probably won’t end up with the corporate keys or the fortune.)
- Getting dumped (If you still have your job, you will have to see him every day thereafter with a smile on your face!)
- Losing friends (…unless your friends want to hang out with you and Mr. Over 50 when his wife is out of town.)
- Being called out by his young child. “Mom, Young Hottie was over here yesterday when you were at the spa.”
- Spending more on therapy (You’ll probably need therapy to figure out why you have put yourself in such an ass-backward situation.)
- Losing the respect of those closest to you (Think: The Scarlet Letter – if you haven’t noticed, adultery is still looked down upon.)
- Catching quite a few STDs (You think you’re the only one he’s sleeping with?)
You may temporarily…
- Get ahead in your career (You’re not the only one getting…head.)
- Make more money (In some circles this has a term.)
- Have insider access to information
- Have more influence when it comes to decision-making
So I ask you, is it worth it?
Don’t take this as a threat – it’s just the honest truth as I see it. Unfortunately, I have witnessed quite a few of you who have dabbled in this arena. It is a steep downward slope and you will be the one torn apart and alone at the end of the day. I suggest putting your energy towards working for that raise and additional responsibility. Now that’s an idea!
Isn’t an Introduction enough?
I fancy myself a “team player” and I like to fix up my friends with each other but when it comes to dating, a lot of people need way too much help.
Yesterday I told a guy friend of mine to check out one of my single girlfriends on MySpace because I thought they’d be a good fit. After looking at her pictures, he writes me back and says, “Please arrange a meeting with her in a casual non-blind date environment.” WTF? I never said I was planning the date for him! Did I mention that this guy is in his 40s? Hasn’t anyone ever told him how to sack it up, be a man, and ask a girl out on a real date?

Now I’m worried. If I let him plan the date on his own, he’ll probably do something really lame. On the other hand, I really don’t want to have to hold his hand all the way through the date set up. What’s next? Is he going to need me to come on the first date with him? Crap! Either way this is NOT looking good.
From now on, I’m going to have to institute an “Introduction ONLY” rule. If a guy friend can’t do something with that, he’s probably shit out of luck anyway. You’ve got to be able to close, that should be the lesson learned here!
Who’s paying for dinner?
There are many differing opinions on this subject, especially in regards to different situations, who asked who out, how many times you’ve gone out, etc. etc. but I’ve come to decide that none of it really matters. Here’s the simple answer….
It’s a test.
There are so many different intricacies that go into the moments that happen after the cheque arrives at the table. How long it takes each of you to reach for your wallet, who grabs the bill, how long you argue about who’s going to pay, whether you even offer at all. Each of these things are indicative of how compatible you are.
I want a guy who has his credit card out when the bill comes and tells me to put my damn money away when I reach for my wallet.
My friend Lisa prefers not to reach for her wallet at all and instead send a polite text message thanking him for dinner the next day.
Another friend Julie doesn’t mind chipping in or picking up the whole bill if he’s ok with it. As long as he gets it next time.
There’s no one right answer for any particular situation. The post meal behavior says a lot about how well you’re likely to get along. Just go with it, do what you really want to do and what would be perfect in your ideal universe and you’ll learn a lot about the person you’re dining with.
I went on a second date a few days ago. I have a policy of offering twice to put my card down (with absolutely no intention of paying for dinner) and he accepted on the second offer and made some sort of weird not-quite-split-down-the-middle math on the bill where he ended up paying more. Which only served to further irritate me. I then got a kiss on the cheek in the car when he dropped me off. On the second date. This is already not working out for me.
I guess I should probably mention that you can send your questions to charlotte@insidestorydating.com.

