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female
age
41-50,
anonymous
writes: I’m confused and would appreciate your help. I have been seeing this guy for 2 months and our dates started with walking, coffee, one time out for drinks couple of lunches and most of the time at his place, either he is cooking or most of the time me. Here is some background: I’m 40 he is 52. We both are divorced with no kids. We both have great jobs, I make six figure but he makes 3 times more than me, no debt. I’m an independent woman and have never relied on any man even my ex husband. I admit that I’m kind of spoiled. I had two relationships before this. Both great guys and treated me with love and respect. Lots of efforts to win my heart and treated me like a queen. I ended both as they started pushing for marriage and I wasn’t ready. . Anyways this guy is kind of different and confusing. After a month and half he decided to take me out for dinner! I ordered something small and the entire bill with tip was about $150 , I saw the number on the bill from the far, which is not even very expensive. He has mentioned that few times that if I liked our expensive dinner! And how I liked it that he took me somewhere nice! This is the first time I’m experiencing this! I was so surprised with the manners! Who takes you out and reminds you few time how nice and expensive the place was. He asked me to get something for him which was around $170 but I gave it to him without asking him to pay me. I have been cooking many times and pay for small lunches as well. I don’t mind it at all and that’s how the relationship should be. My ex boyfriends were taking me to many nice places and I never expected it but this guy took me out once and has mentioned it few times! Should I tell him something? The funny thing is he goes out by himself to some most expensive restaurants in the city and send me pictures of his food and never mentions anything about the price. I’m confused! why he is doing this. He keep telling me he is not a wealthy man and he wants me to want him for who he is! I don’t expect anything from him but his comments makes me uncomfortable. I don’t think he is cheap. He mentions about the stuff that he has given to charities . Is he testing me? Honestly I don’t care and don’t need anyone’s money. I earn enough and don’t need more! He was asking me to take him out on lunch which I don’t mind but the it’s just strange. What do you think? Is he doing it intentionally?
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female
reader, Honeypie  + ♥, writes (28 January 2018):
You are smart lady, OP
2 months of dating is definitely too soon WAYYYY too soon to think about moving in together. For him to ask about THAT but then worry about ONE dinner expense, it's odd. I can see why you find it confusing. Especially if he suggested that YOU live with him so YOU can save money and then he makes SUCH a big deal of the price of ONE meal.
Something is off. So pay attention.
A
female
reader, anonymous, writes (27 January 2018): Thanks for the advices. I will talk to him and make it clear. He already knows that I’m not a materialistic person. I walked away from my marriage without getting a penny from my ex, I could collect at least 3 million dollars. I didn’t do it because it was his money and I wanted to be fair.
This guy gives me mixed signals! I haven’t purchased any house yet as I wasn’t sure if I wanted to stay where I am. I’m renting a nice apartment and he was hinting that if I move in with him, when I feel comfortable to do it, I can save my rent money. I said it’s to early to talk about this.
I have been in some restaurants that he goes by himself. Dinner and multiple drinks that he ordered is not cheaper than $250 and I know it’s not paid by the company. He sometimes invites his friends too! So it was kind of confusing for me. He knows I’m particular about almost everything and I can afford it myself. It’s so silly to even mention but every time I cook there it doesn’t cost less than $100 as I purchase the finest materials and it’s my choice. I find it so disrespectful to even mention it in return and I have cooked there many times. He is very particular too yet mentions about the one time dinner out! I found it just odd.
I just cannot stand cheap and stingy people as it doesn’t just apply to money. I absolutely don’t expect him to spend anything on me but can’t stand him taking me on a date and treats me this way! It was his suggestion and I even didn’t pick the place as I didn’t care.
I will talk to him and will observe how the relationship goes and if I feel this is the case I’ll end it.
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A
reader, anonymous, writes (27 January 2018): I think you're both a little "cash-conscious." Both being successful people, it's a little difficult not to be aware of your success and wealth. I think he may be sending a shot across the bow to let you know this ain't always going to be about what's in his wallet. He might be a bit of a miser.
Personally, I would be very much offended. However; you could always let him know you're perfectly capable of sharing the cost of a date; and don't need to be reminded of his generosity. Say it with jest and finesse. Counter him every-time he brings it up. Use behavior-modification. I don't mean you have to be a harpy and constantly chastise him. When offended, say so. He needs to hear it a couple of times, and hopefully he'll get it.
He's probably used to women dating him for his money. He's letting you know he's no sucker and he's not cheap either. I'd say he's making his point in a very tactless and presumptuous way. To some degree he does have to figure-out if you're there for the money; or do you truly see something in him. Your actions should be sufficient.
Perhaps he can't differentiate between the finesse/charm we use in romance; and the savvy/directness we use when making a business-deal, or dealing with an adversary. He needs to be reminded who you are, and to lower his defenses. You don't need his money. I think your concern is justified, but don't be too alarmed. If you're not clear, seek clarification.
Open-communication is very important in relationships. Like mother always taught us; "use your words." You came to us and told us how you feel. Tactfully, you should convey your feelings to your man-friend. Assure him that it's definitely not about the money; and you certainly hope this is more than a "merger" or business-deal. You're looking for respect and hoping to establish a meaningful-relationship. Wherever this goes.
In the past, he may have been played or used by other women. So you have to reprogram his thinking. You are not those women. You do like nice restaurants, you also enjoy the finer things in life; and you can so easily provide them for yourself. You are hoping to share and find something meaningful between you; and you don't really want money to be the crux or core of your relationship. You've worked hard and you're looking forward to finding someone to share all the success you've achieved. Money can't buy love, and you're not for sale.
Choose your own words. Borrow mine if you like. He's testing you and also "schooling" you indirectly. Flip the script! Question him and find-out where he's coming from with offering you a financial-report and reminder-notice following a date. You're not impressed about his money. You expect more of him character-wise. You're not that kind of woman.
Throwing how much you spend on someone up in their face is disrespectful and quite condescending. If simple communication about how you feel about it doesn't work, or isn't sufficient to make it stop; then dump him and move on.
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A
female
reader, Windbreeze62 +, writes (27 January 2018):
 I am not understanding the mental abuse that he's taking you through. He's mentally slapping your hand everytime you go to an expensive restaurant. Go to a Waffle House or an IHOP and let him pay the bill then see what he says. I think he's using the money as a way to shield his insecurities of the reason why you are in a relationship with him after all you are twelve years younger than he.
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A
female
reader, Honeypie + ♥, writes (27 January 2018):
1. I don't think you should BUY him $170 stuff 2 months in. Just no.
2. $150 meal for 2 people is kinda steep in my book but then again I don't eat out at fancy restaurants.
3. TALK to him, ask him straight out.
4. Giving to charities doesn't mean he is generous, after all donations to charities are often good for tax write-offs.
My guess is he liked the IDEA of taking you to a fancy restaurant, but I don't think he expected a $150 bill. So in the future I would perhaps suggest going to less expensive/fancy places to dine.
What I don't get is that HE suggested the place and HE is the one surprised it was expensive. So maybe he hasn't been there before (OR when he has gone there in the past someone ELSE paid, like his company etc.)
You need to talk about this. I think HE needs to know that you do NOT expect (unless you do, then tell him that) expensive meals, fancy wine or whatnot. Because that is what I think he is hinting at. That he doesn't FEEL he can afford to pay for expensive meals. (even if he can) Spending a LOT of money going out to eat is apparently not a thing he is a fan off.
And yes, I actually think he is testing you, that is why he asked you to take HIM out for lunch.
To me this seems so odd for a guy in his age (he is from the time where it was DEFINITELY the norm that the guy paid for the dates.) So I actually do think he is a bit cheap. But you won't know unless you bring this up and talk about it. Just remember one thing, it doesn't mean that you now OWE him because of this one fancy meal.
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A
female
reader, Youcannotbeserious  + ♥, writes (27 January 2018):
 Why have you not had this conversation with him? Anyone on the outside can only guess what his motives are or how he views money. It could be he is afraid of attracting a gold digger. It could be he is very mean with his money. It could be he has been short of money in the past and now values what he earns. It could be he is one of those people who is obsessed with money. He could just be socially awkward and not realise what is "appropriate". There are endless possibilities.
Money is obviously not as important to you as it is to him, at least on a day to day basis. You seem to have a far healthier approach to it than he does (based purely on what you have posted).
You are only a couple of months into the relationship. If this is already a source of concern/irritation to you, it is probably only going to get worse. My advice would be to actually have a conversation about it with him. Just ask him why he keeps bringing up one meal he took you out for. Maybe he is not used to taking ladies to nice restaurants and thinks it is a bigger deal than it obviously was for you? (Personally I would faint if a bill for two light meals came to that amount of money - the sort of money I would spend on two weeks of food shopping - so you see, we all have different standards.) Just because YOU thought it was no big deal doesn't necessarily mean HE didn't (regardless of where he eats at other times).
You two really need to talk and you need to find out more about where all this is coming from and whether you can/want to put up with something which is obviously irritating you.
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A
male
reader, anonymous, writes (27 January 2018): I wouldn't like this. He maybe "testing you" as you said, but if that is true would you want to be with that kind of a dude? That sounds manipulitive and passive aggressive
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