“There is no need to show your insecurities by asking her to fly to Cancun or schedule a driver to French Laundry”

While checking the pulse of the internet for hot topics we discovered there are over 10,000 Google searches per month on the keyword “Dating Advice” – Really?!  Very much like driving a shitty car will eventually cause you to learn about automobiles, being single in your forties allows for a plethora of dating advice at your fingertips, and we have a few here at TRM.  However we did do some research to offer our usual blend of entertainment mixed with some all too important advice.

1. Ask Properly, Keep Perspective. This is where it all begins.  If the girl is not giving off The Vibe, or being fickle or maybe she is slightly out of your league, then don’t push it!  Set an achievable goal.  If you can get her away from her friends, and most importantly your friends, for a couple hours that’s a win! There is no need to show your insecurities by asking her to fly to Cancun, or schedule a driver to take you to Maestros, French Laundry, Auden Bistro or whatever Faux Celeb spot you have in your locale.  Keep perspective.  If it’s a blind date, then coffee or glass of wine on a Sunday afternoon is great.  Hang out for an hour, if it goes well you can turn it into a light dinner, if the vibe isn’t there, EVERYONE has somewhere to be at 6pm on a Sunday – home, so there are never any hard feelings about ending your engagement.

2. Be A Boy Scout – Be Prepared.  This is more about a test than it is about your ability to select a restaurant.  Just like women will judge you on your shoes, they will also judge you on your preparedness. Women do not want a guy that can not plan a date.  Why?  Because they think the rest of the relationship will be a pain in the ass, and they are right.  Even the most independent women want a man to be able to plan an evening – it’s not rocket science, its not even Twitter.

3.  Be Familiar, But Not Frequent.  Picking a restaurant or venue that you’re familiar with will always have its advantages.  You understand the seating, the parking, how long it takes to get there and the good times to go.  You can call ahead and ask for a certain table and you can describe to your date best way to get there and where to park.  This can backfire if you are Norm from Cheers and people are constantly interrupting.  It can also backfire if you have a (lame) bartender or server who doesn’t understand The Code when waiting on a single man, and mentions that you were in there last week with another woman.  Pick a place you are familiar with, but not a regular.

4.  Give The Lady First Dibs.  Do not be an ass and race out after the hostess once she grabs menus so you can select the best seat.  There is always a ‘best seat’, understand that and let the lady choose.  They will surprise you and often don’t care.  If its a 2-top perpendicular to the wall, then one person is going to have their back to the entire restaurant.  This would drive me insane and I would ask for another table, but some people don’t mind.  Give the lady first dibs.

5.  Cash Is King.  You MUST carry cash on a first date with different bills.  Things will come up where you need to tip, or pay for parking, etc.  You cant be running over to an ATM or waiting for a cab driver to find you change, or worse allow her to give you money.  Cash is not king , it’s REQUIRED on a first date.  Better to be late picking her up than to arrive without cash.  This is one of those judgement things, women want to see the date go smoothly … and so do you.

OK Grasshopper, we got you to the restaurant, we got you seated, now you should probably read about Annoying Words On Menus, until we show you how to behave during your date.  Until then, don’t do anything foolish, tell her she looks great and we’ll be right back.

Thanks For Reading!

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