We have quite an age gap. I’m 21, he’s 42. He has a nice paying job, lives in a condominium, has a car, etc.

This happens everytime but let me tell you about this one time. We went to starbucks for coffee and to chill. As always, we pay for our own food, unless we mutually agree to share, in which we pay half-half. I’m okay with this because I have my own money. I never expect him to pay even though he’s way older than me.

He insisted that we use his card because he wanted to collect stars. He ordered, and I waited for him in our seats. When he came back, I asked how much do I owe him. He said he threw the receipt already, and he’d just ask the barista before we go home. However, he forgot about asking the barista.

On the way home, he’s using his phone to search for the price of my drink and the food we shared (in which he even begged me to eat more than half because he badly liked it, lol sticky cinnamon bun). It triggered me and told him that it could be outdated. He got mad and told me that I couldn’t dictate him what to do, so I said lol okay.

When we got home to his condo, he told me that I owe him a price which is more than what I expected it to be. I said “no way””, but he said it’s based on what he saw. Apparently, he based his prices on grabfood which is higher priced than normal. I realized I can check the starbucks app, so I did. I told him about the price that I owe him and he said “Okay, but let me check again. let’s just adjust later if it’s wrong”. I sent him the money already.

This guy is just straight up hilarious. While writing this down, he’s still searching about the price of a grande matcha latte. Whenever I have leftovers, he would eat it even though it looks like a mess and it’s literally a tad bit left. I remember one time I’m taking a shower and he literally went to the shower room just to tell me the amount of the food we just ate.

There’s no way I’d romantically connect with him because of other things aside from this. I do enjoy the bed scene though. But what do you guys think about this kind of person in general? I kinda get the reason why he’s still single in his 40s lol.

Tl:dr: Guy I’m seeing is very keen about money

25 comments
  1. the answer is NO. I’m 45 and from my perspective that is just..ok let me put it this way.

    Consider this. How would you feel about dating a 14 year old boy? Now aside from the obvious no no involved.

    How easy do you think you could impress and manipulate a 14 year old?Condo+car? thats about as standard for a 40+year old as a car and a job is to a 21 year old, compared to a 14 year old.do you think your interests would align? do you think you would see him as an equal? Would your interests in life be similar?

    Now you add a 20+ year gap. You are nothing more than a pretty thing to have sex with.

    Also the older people get the more stubborn they become about who they are and how they handle/view things.

    If you where at least 35, then I’d say yeah that could work.

    Whatever time you spend with him, will just be time wasted.

  2. I think you’re being awfully naive: this behaviour isn’t quirky, it’s pathological. Combined with a sexual interest in people 20+ years younger than him I’d be running for the hills.

  3. No guy in his 40s goes into a relationship with someone half his age because he wants to have a mature, healthy, balanced partnership of equals with her.

    He does it for one (or more) of exactly three reasons:

    1. He himself is so immature for his age that women close to his age aren’t willing to put up with his childish nonsense. So he has to go and find someone who is decades his junior in order to seem mature enough for her.

    2. He doesn’t want a partner, he wants someone to *dominate*; he knows that a person much younger will be far less experienced, and whenever there’s a conflict between what *you* want and what *I* want, well, gosh, you’re just so young you don’t really know how the real world works, whereas I’m so much more experienced and wise, so we’ll just do it *my* way, m’kay, pumpkin? Bonus points if he manages to make it seem like the reason he’s overriding your ideas is for your own good, and thank goodness he’s there to do that for you, or you’d just be in a mess all the time.

    3. He wants a toy that he can use for a while and then toss aside. So he looks for a young, naive person he can shower with compliments and so forth in order to get her infatuated with him, so that she’ll *be* that fun toy for him to play with for as long as he likes, and then, once he’s had what he wants and she’s no fun any more and she starts asking for things like “commitment”, oops, so sorry, he has to go, and he kicks her over the transom so that he can go find *another* new toy to play with.

    Add to all of this the fact that he has a mean streak:

    > He got mad and told me that I couldn’t dictate him what to do,

    …over something pretty trivial, and you have quite a piece of work on your hands.

    There’s no good for you here.

  4. If you want to enjoy the bed scene with him, enjoy to your hearts content. But he seems like horrible relationship material. The age gap is incredibly creepy when factoring in your age (who cares if a 40 year old is dating a 60 year old) but a 40 year old dating someone just old enough to drink… gross.

    His fixation on prices is a red flag. Especially when he was effectively trying to steal from you (quoting the highest prices he could find). If you like split finances, you keep the receipt

  5. A guy in his 40s going after a 21 year old is all kinds of yikesy. I’m in my mid 20s and dating a 21 year old would be sorta weird even though the age gap would be like 5 years.

  6. Old dude is nickel-and-diming the *21-year-old* he is dating. Like c’mon, this dude is a loser.

  7. This guy sounds awful. He’s cheap, obnoxious, and inconsiderate. You could have easily just paid for your own meal, but because he wanted all of the reward points he had to pay for both of you and then spend a half a day quibbling over a few dollars. I cannot imagine someone this idiotic and selfish is good in bed, but if you enjoy sleeping with him by all means continue. Just don’t go on dates.

  8. He’s double your age, you are in such a different part of life than each other. Find someone closer to your own age.

  9. If you’re gonna date an older guy, at least pick one who’s going to be a little bit generous with his money.

    I mean, I regularly buy my bestie coffees because it’s a nice thing to do – it’s pretty weird that he refuses to even drop a couple quid on you.

    ….not to mention a 40-something year old dating a 21 years old is all kinds of wrong.

    Ditch him – you can do so much better! He sounds like a complete loser.

  10. I see statements like “he has a good job”, “he owns his own X”, etc. like this a lot and I want to point out to you or any 20-something in the USA who needs to hear this: owning a car, condo, car, and having a nice paying job are an unusual/special/unique milestones for someone in their 40s. It is also an indication of a person’s character. People with nice jobs can also be cheap, stingy, rude, immature, etc. Having this things should not be a reason to like/admire something.

  11. This is not the guy!
    You’re at an age where it’s perfectly normal to want to have fun with someone older that you know you won’t be committing to. But that should be because it’s fun and it has its perks. I’m not talking about using someone or someone being your sugar daddy, but if you are dating someone old enough to be your parent they absolutely should be treating you to things! The fact that he isn’t says a lot about his character and probably the financial choices that he’s made in his life. Regardless of gender norms, or relationship roles or any of that, you are at an age where you should be saving your money and building your future, he is at an age where he should have had it all figured out for a while.
    You should always feel that whoever you’re dating is generous towards you, you shouldn’t be dealing with this kind of pettiness.

  12. Honestly, the age thing is a HUUUGGGEE red flag.

    I am only 31 and would never be interested in dating a 21-year-old because (no offense) you’re pretty much still a child. This man is old enough to be your father.

  13. No woman his age would put up with his shit. I’m all for paying my own way, but if he said he would pay then that’s his choice. He can’t come after you for the money later. Either dump him as a boyfriend and keep him for a friend with benefits arrangement, or find yourself a better boyfriend

  14. This is bizarre. I wouldn’t go anywhere near this weirdo and I’m a lot closer to his age than you are.

  15. I can’t believe you’re dating someone twice your age who won’t even pick up a coffee just once. He chose a 21 year old for exactly this reason.

  16. Don’t do it. You will age out and he will find someone younger. Find someone your own age.

  17. He is with you because he knows no 40 year old woman would let him treat them that way, try and find someone your own age where you see a future

  18. What the FUCK IS THIS, I’m your age OP and all the relationships I’ve had we share money on a very rough basis, which means it’s probably 50-50 but nobody cares, I’m sure that guy would ask you to pay for gas if he ever took out his car, plus he’s fucking 41, I understand the bed scene must be good but it’s not impossible to find someone your age

  19. Why the heck are you wasting your time on this guy who is too old for you and penny-pinching?

    Move on with someone closer to your age and knows how to treat a date right.

    Oh, by the way since he insisted on paying with his Starbucks app – the receipt is available for him to see at any time.

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