Dating Advice for the Definitely Not Dead #2

Wow!  The first week of the dating advice column blew up my inbox with questions on everything!  (And I do mean everything.)

A number of women have commented that they have gotten away from being the pursued because they have to be these aggressive women in the corporate workplace.  That may be true for you.  But as you already know, what's good for one is not always good for another!    So keep on letting those men pursue you!  You will get a man who really wants to be with you.  Men, you will know if she is a patient person and willing to wait for the best (that's you).

So without any further ado...

Q:  Who should pay?
A:  There are about as many opinions on this as there are noses (or other apertures), so here is my semi-professional opinion:  (And there are two parts to this answer, so read the whole thing) Not only should the MAN plan the first five dates, he should also pay for them.  Here's my reasoning:  Mr. Wonderful has pursued Miss Fabulous and, since she has made herself accessible but not easy, he is very pleased with himself that he has garnered a date with Miss F.  Since he is a man of action, he plans a date that is great but not the best date ever.  (Save that for later.)

He has planned it, so he knows what kind of financial commitment he is making. Miss F is undoubtedly making her own preparations, because she may decide that her current wardrobe choices are not gonna cut it and she needs something to accentuate the positive.  Or that she needs a blowout.  Or a manicure.  Or that Chanel red lipstick she's wanted for some time.  Girl World is complicated and not cheap.

PLUS, assuming Mr. W and Miss F go on a second date (and third and fourth and fifth), roughly three to five weeks will have passed and if she is any kind of woman you really want to be in a relationship with, she will be oh-too-glad to express her appreciation by say, cooking dinner, or picking up the check on date 6 or later.

Now, in my humble opinion, this is where the check-sharing can start.  If Mr. W and Miss F are "dating" per se, why in the world would she assume that he would pick up the tab forever?  He's not a prize in an all-you-can-eat contest.  Ladies, assuming that you have a job that pays you beyond your normal expenses, you need to pony up and take turns paying for dates.  If you are in any other payroll situation, get creative and go on free dates.  There are many things you can do in a city for free. Or scour Groupon for cheap dates.  Take a picnic--that's romantic. But make your relationship one based on mutual respect and admiration.

If you like him well enough to go on six dates together, you either like  him and want to continue to developing a relationship OR you are PLAYING HIM, and the words I have for that are words my momma taught me not to say.  But  you know what you are.  And if you happen to be outrageously beautiful, you STILL DON'T get out of paying after so many dates.  I have heard women say that "men should pay for the privilege of being seen with me."  So men can pay for your company?  Does your entitled attitude come along for free?

That whole mindset makes you a paid monkey.  And women are better than that.  Way better.

Q:  Who should initiate the first kiss?
A:  Gentle readers, since this is a column for 40 somethings and wiser, I think it would be foolhardy for me to tell you who should initiate the first kiss.  Plus, there are so many varieties of situations I can't even count them.  I mean, there's the "meh, how can I avoid being in a situation that would make kissing possible" all the way to "we have such incredible chemistry we must kiss NOW."

Think back on all the first dates you have ever been on.  Was any one the same?  I doubt it.  (If you've been on a lot of first dates and not a lot of second ones, that is a question for another column.)

Here's a guideline:  In that moment, go 90% there and let that other person come to you the other 10%.  It's either going to be there or it's not.  Yeah, it's from a movie, but it's great advice.

Alright, love me or hate me but send me your questions and comments to  You may just see your question on the Definitely Not Dead.


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