How To Introduce Howie to The Family

Carole writes Howie:

 

Well you could set a calendar by my body.  The next date to watch out for is Mar. 20, which works out perfect as I should be in Ft. Worth for the last of it and over it by the time we leave for NY.

 

You mentioned that you were booking rooms and flights.  Let me know what I owe you and I will bring a check.  You agreed early on that I could pay my own way on trips.  You also set the rule that if you ask me out somewhere locally you pay and the reverse is necessarily fair, so I put your 40.00 in the front cover of your book downstairs where Crystal sleeps.  I can see that this could become a huge test of wills and creativity in trying to find some way to pass the money back and forth, if I didn't remind you of your own rule ;-)

 

I am uncertain how to proceed with getting you and my family all around a table.  I always pay everyone's way when our family gets together.  My mother will sometimes try to fight me for the check, but usually concedes unless it is my birthday or something.  My father doesn't eat with us unless it is my birthday or his.  My extended family has no problem in letting me pay and none of my mates has ever had a problem with it, except Jay, but he made 400k a year and was in the habit of feeding huge troops of people that he called friends.

 

I don't want to make you uncomfortable, but I don't want you paying the bill either, because just my brother's clan can be 5-8 people, so I am open for suggestions about how to handle this.  If you want to split it with me at the time, I can reimburse you in cash privately later.  I get a couple hundred in cash per month that I don't have to account to anyone for.  (Jamie reimburses me for her insurance in cash each month, not anything weird...). I am late for the gym.  - Carole

 

Howie writes Carole:  You have left me quivering this morning.  Uncle....I concede on the $40 and will find it.

 

It has always been my habit to play the traditional male role and pay for dates.  And while the women I have dated have generally had careers, in most cases I was better off financially so this made sense.   Most occasionally wanted to reciprocate, particularly if there was a reason like treating me for my birthday or as a special thanks for something, or just to participate occasionally.  I'm not a fanatic about it, I just don't want you, out of past habit, thinking you have to bear the brunt of our entertainment expense.

 

Separately, I think it is wonderful that you have been so financially successful, far more than I have.  As far as I know, I don't have any big ego issues about that, but I think I would have a problem feeling that you were bearing the brunt of expense.  If you were someone who enjoyed expensive things that I felt I could not afford, like exotic trips, there might be a problem because I think I would feel "kept" and be very uncomfortable.  But you don't, so it does not appear to be an issue.

 

Let's chat about family.  Some thoughts:  Gathering them all around a table is probably not a good way to meet them.  One can only chat personally with one person or couple at a time.  I'd be more inclined to meet your sister and brother on one occasion, your mom on another.  If you dad does not tend to participate, it could be just lunch with your mom some time.  And one way to avoid the check issue with your brother is we could do dinner here, which I would be delighted to do.  If it is really important to you to pay for part of the food for that you can, but it really is not necessary.  A better idea would be to let me do that, and then another time when we might eat out with them you can pay if you like.

 

There is no rush or urgency either.  I'm interested to meet your Mom and brother because they appear to be important parts of your life.  But I don't feel left out or have any problem with not having met them or not meeting them, and I certainly don't want it to be something that causes you any