Some sugar daddies are poor at covering up their tracks if they’re messing around on their wives or significant others, what’s worse though, is the time of year you choose to two-time (intended pun).

Over the last few years, wives and significant others have been clueing into Mistress Day, February 13^th, the day when most men can get away for a moment to celebrate their Valentine on the side, their wives none the wiser.

This is a REAL example of how that can go down (in flames):

Married Sugar daddy wants to celebrate with his sugar baby Valentine

Rather than actually seeing her on Valentine’s Day (a day for his wife), he chooses to see her on Mistress Day, the day before Valentine’s Day, to wine her dine her, and take her shopping!

An almost good plan, he decides to get them both the same gift, thinking he can kill two birds with one stone. One for his old love, and one for his new love… That’ll keep things on the straight and narrow, right?… Ah, no, not quite. You see, with anything purchased, there is a paper trail out in the world somewhere, proof of infidelity, or dishonesty at the very least.

Who does sugar daddy’s laundry but his wife? Receipts or purchase orders are always stuffed in a pocket with quick haste.

Sugar Daddy’s wife does laundry (at least she does something around the house, as minor as it seems) and finds the receipt for the two identical gifts, she remembers she only got one… hmmm… that scenario can bankrupt a rather unsuspecting married sugar daddy quicker than the market credit crunch.

Wives can easily discover one of the following in the month of February (so hubbies, don’t fall victim to this):

• Gift receipt for the exact same two items and she received one
• Sales person at La Perla sent a hand-written card through the mail, thanking you for purchasing a gift she never received
• Hotel or resort confirmation which didn’t include her
• You are NOT actually at work for a new time consuming project, she already checked
• She receives the wrong lingerie gift (she’s a size 10 and your mistress is a size 2—awkward…)

Married Sugar Daddies—your wives are out to catch you in the act of infidelity, an expensive and silly reason for you to overlook minor details to cover your tracks.

Think about these things, and whether or not you can be easily caught. You want to have your sugar and eat it too? Then be careful, learn from Kelsey Grammer’s possible $50 million dollar mistake!

I wanted to follow-up about my Monday post regarding sugar baby dating using a hotel room. Although my last explanation was directed more toward the millionaire sugar daddy who isn’t doing the extra marital dating thing, this piece of sugar baby dating advice is directed toward any and all wealthy men using SugarSugar.com to date sugar babies online. It’s about the kind of hotel you should take your sugar baby to.

I guess when I suggested taking a sugar baby to a hotel some people thought I meant a trashy truck stop style motel. This isn’t a prostitute… and you’re a millionaire sugar daddy. So cough up the cash for the Ritz like a good little rich benefactor. Otherwise, if you try to cheap out, you’re going to send the wrong message to your potential sugar baby. You’re going to send a message that you’re not really a millionaire sugar daddy you’re not intending to let her have any of the benefit in the mutually beneficial relationship you’re proposing.

Last Monday, I wrote a post referencing that I take my sugar babies to a hotel. Some people tried to call me on it, asking why, if I was a millionaire sugar daddy who wasn’t extra marital dating, would I take a sugar baby to a hotel instead of my presumptive mansion.

First of all, I don’t live in a mansion. Why do so many people believe all wealthy men live in mansions? I’m a single male in my fifties… what do I need with a Mansion out in the middle of the suburbs? I don’t want to clean all that space, and I don’t want to be an hour away from the events of the city. So I don’t live in a mansion… I live in a downtown condo. The space isn’t as large, but trust me… the rent ain’t any cheaper.

So the next question would logically be, “why don’t you take your sugar baby dates to your condo?” The answer to that is pretty simple: I don’t let random women know where I live. Why bother? I don’t even take girls I pick up in bars to my house, let alone girls I just met on SugarSugar.com. It’s cleaner to take sugar babies to a hotel… at least the first few times. And I don’t mean that in a “wild sex” sense (though that’s sometimes the case… first sugar baby dates tend to get a little wild because the girls are trying to impress you, but I have a housekeeper). I mean if the dates don’t go well — and sometimes they don’t — you don’t necessarily want a girl you don’t know able to show up at your house without warning. Makes sense, doesn’t it?

Planning the first meeting

When it comes to planning the first meeting a lot of emotions are in play. Anxiety is in high gear, excitement, fear and happiness. Both parties have invested plenty of time getting to know each other, this first meeting is the time where chemistry is tested. It determines whether an arrangement will ever come into play.

I would suggest that the Sugar Daddy asks the Sugar Baby to choose the place. He should provide her with an area where he is comfortable with and there is minimal chance of running into anyone he knows. The SB should provide couple of places from which the SD can choose. This way both parties are comfortable with the location and that bit of anxiety is taken care of.

I would suggest that the first meeting takes place in a public place. Sugar Babys take the time to choose a place where you are comfortable with. Know how to get there and be on time. Meeting for drinks or coffee mitigate the risk of being stuck with someone you do not like for hours having lunch/dinner. Meeting for drinks always allows the option of moving on to dinner if there is some sort of a connection. If you opt out to meet for coffee, choose something other than Starbucks. The place is too busy to have a private conversation. However, a small coffeehouse allows for an intimate setting where both parties can enjoy getting to know each other.

Tip of the day: Limit your first meeting to 45 minutes to an hour. Then go your separate ways! If you feel like you should have spent more time with the other person… well that means that you should see each other again!

Happy meeting sugars!

Be careful when revealing your true identity

For sugar babies it is key to find out if the person we are speaking with is indeed capable of being a sugar daddy. This often requires finding out who they are. Doing our due diligence before meeting is key. As such we request the person’s full name. For a sugar daddy discretion is paramount. If he is in a high position revealing his identity is a big step. This causes a conflict, as most SDs refuse to provide a picture in order to protect himself from being found out. This of course puts us in a predicament.

Taking some time to get comfortable with each other is the only solution. It is important that both parties provide comfort to each other and ensure discretion. Usually, communication should include finding out whether the parties are indeed compatible for an arrangement. If you are not then there should be no need for either to reveal their identity. Finding out what each party needs and is offering over the first couple of emails saves time. If there are red flags in the beginning then move on and continue searching. However, if the needs and limitations align and there is a level of comfort then revealing the identity is part of the course. Do it wisely … and provide it only if you have interest in meeting the other person.

Get a mischief phone!

This is very simple to get, a track phone is an excellent option. An SD can keep one just for sugar dating and can leave it in the office when he does not want to be reached. For the SB a second phone can provide her with an additional layer of safety in case sugar potential turns sour. Of course this requires him/her having 2 cell phones and that is an additional hassle.

If this option is not for you and you prefer to have one phone only then the google voice application is for you. This requires you to have a smart phone, which in this day and age should be no problem. Go too google.com/voice and get one. It might take you a while to get approved but once you do the wait will be worth it.

What the geniuses from Google have come up with is a free cell number which you tack on to your personal cell. You can manage your access from their site which looks similar to the gmail website. It allows you to forward all of your calls to your cell phone. In addition, you receive a text mailbox which you can forward to your phone or access from the application which you must install. The super nifty feature of the service is voice mail transcriptions. I personally HATE checking voice mails and with the google voice I don’t need to do so anymore. The voice mail is transcribed and sent to me in a text from.

Last, if you have ever had to block someone from contacting you I am sure you have found out just how difficult that is from your cell carrier. Not so with google voice… it is just a click away and voila you will no longer hear from this person. You can also opt out to have that number go to voice mail straight away. Of course this voicemail can be set up just for them. Yes that is right you can tell the person you are no longer interested by never speaking to them… awesome right?

So now I expect google voice to be flooded with new requests.

You are very welcome sugar world!