Dating Question for Single Moms

Updated on March 25, 2013
M.S. asks from Lincolnshire, IL
9 answers

I am recenty divorced and started dating again for the first time in 15 years! I have been dating the same man for about one month. Everytime we go out, he pays for everything, never even giving me the chance to offer to pay. He seems to have plenty of money and owns his own small buisness. I work part time and would not say I have a lot of extra money, but some extra ;) My question is, what is the dating rule? Should I let him continue to pay for everything or offer to pay once in awhile? I feel like this is a whole new world. Last time I was dating I was 25 dating other young men in their 20's. Dating in your 40's in a whole new ballgame!!
Thanks

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T.M.

answers from Modesto on

I'd let him pay, he was taught to it seems. Most men like to pay I believe... You can always offer to leave the tip maybe?

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J.W.

answers from St. Louis on

I always grabbed checks. Most guys will say I got it but sorry, I make money, maybe not as much as them but I am no meal digger.

I think it sends the wrong message when you just throw up your arms and say take care of me sweetie.

I was 38 when I divorced, 41 when I met my husband. I always paid my share.
_____________________
Just so you know, and this isn't across the board, but a lot of the guys that were adamant they pay got this idea they were paying for services. Not all but enough that there was no way I was giving them the idea I could be bought with food.

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C..

answers from Columbia on

I divorced in 2005 at the age of 34. Here is what I did....

1. I was always *prepared* to pay for the entire bill. I'm not going to be a part of something for which I can't be responsible. Even if I'm not going to pay, it makes me not dependent on him TO pay.

2. I always offer to leave the tip if he buys dinner.

3. If they picked up the first check (and I wanted to see them again) I would say - "Thanks, how 'bout I get next time?"

4. If we went to dinner and then somewhere separate for a drink, I would ALWAYS buy the drinks if he bought dinner. If he said, "I'll get it" I would say "You got dinner, this is on me".

I have several very defined beliefs about money equality in relationships, as well as single-mom dating, in general so I thought I'd give you a run down, even though you didn't ask.

A) This isn't 1950, so we aren't operating by 1950's rules. Therefore, I can pay my own way.

B) It is nice when the guy pays for the first date. After that, my feeling is that it should be 50/50... because that's what I will expect, in general, in our *relationship* (whatever it may be). You have to set expectations from the beginning.

C) That doesn't mean you split checks in half.... but if you are going to continually date someone you should alternate. or he gets movie tickets you buy popcorn. or you cook dinner he brings dessert and the movie.

D) Don't assume he isn't dating multiple people just because you aren't or because you think you feel a connection. if you haven't had a conversation that explicitly defines you as exclusive, he is free to (and probably is) dating other people. It doesn't matter if you're seeing him twice a week.

E) Determine how you feel about sex. And sleepovers. And how much and what type of contact he should have with your kid(s) and when. Determine these things BEFORE they happen, so that you can have rational conversations when they come up because you've thought through how you feel.

F) Don't introduce him to the kid(s) until you have seriously considered the impact it will have on the kid(s) if you're with him 5 years and then you break up. Because you can say "I think we'll be together forever" or "I think we'll be together long enough that he'll be a good influence" or "we're only casual and I'm going to be the parental figure, so my kid(s) won't get attached". But it doesn't often happen that way. And we've thought about the impact of the kid(s) MEETING our guy. But we haven't thought about the impact of if we are long-term but not forever and there is a breakup and the kid(s) never see the guy again. That's a whole different scenario.

G) Have fun. Don't worry. Deal with the baggage from your first marriage. The stuff YOU caused. even if it wasn't your FAULT, you still have fall-out. So, get your house in order before you invite a house-guest over.

:-)

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X.O.

answers from Chicago on

I think it depends on what kind of tone you'd like to set for the rest of your romantic life. Do you want to be thought of as an equal, or as someone to be taken care of? I'm with Jo on this one.

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S.H.

answers from Honolulu on

I would, offer to pay or at least pay for tips.
Just try and be independent about it.
Because, if after dating for ONLY 1 month... and he has a "problem" with this and your paying for things too... THEN YOU WILL KNOW... what kind of man and personality he is.
ie: Chauvanist controlling stereotype type, or open and respectful of women.
And if he is Chauvanistic and controlling about something as simple as this, I would not date him anymore.

You have only known him for 1 month.
Keep your options, open.

I would also, be very independent and openly express your own opinions too. See how... he reacts to your doing so. Then you will "see"... what kind of man he is and if he respects, women... especially those that have their own ideas. See how he reacts... when YOU take the lead in things, or even where you go to eat dinner.
And yes, I did this myself, when I was dating. Though I did not yet have kids.

This is not the 1940's after all.
See how his attitude is. Toward women and children. And if it is just an act or real.

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☆.A.

answers from Pittsburgh on

If a man is interested in dating you--he can pay! Never feel "odd" about that.
It's a sign of good character, don't you think?

IF you invite him somewhere, you can treat.

(I'm not a single mom, but I'm sure I grabbed WAY too many checks way back when! Lol)

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C.V.

answers from Columbia on

When my now-husband and I were dating, I only paid one time. I was offered an awesome full-time job, and I called him and said "we're going to go out and celebrate....my treat."

It was awkward for him because he feels that a gentleman should pay.

That's how it is for most mature men. They feel like a schmuck if they don't treat their lady. So, unless you're celebrating something big, and you've outlined that you'll be paying prior to the date, just let the gentleman pay.

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A.M.

answers from Dallas on

I try to operate on about a 3 to 1 ratio: he pays three times, I pay the fourth or make him dinner or buy tickets to something special. I have found that if you do 50/50, it makes men uncomfortable because they really dont know how to handle it and it brings confusion to the evening. When it is my turn to pay, I just tell them at the beginning of the night or beforehand that this one is on me. Good luck!

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T.S.

answers from Washington DC on

Dating or not, if you INVITE someone somewhere, you are offering to pay. Period. "Hey, wanna catch a bite after this?" isn't an invitation, so date or not, male or female, you should pick up your own tab. But if he calls and asks if you'll join him for dinner on Saturday, he chooses the restaurant and time, you're just GOING... he's paying.

My SO and I have lived together for two years (dated two before that) and are raising DS together. We split household bills and expenses etc, because we both work. BUT... if he invites me out on a date night you better believe I expect him to pay!

All that being said, I expected that in my teens and twenties as well. No one took me on fancy dates back then, but if you ask someone out, you take them on a date you can afford... without them pitching in.

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