I’ve been seeing a guy for about 2 months now and I can see a lot of problems that can arise if we get more serious. We have a date tomorrow and I am lying in bed thinking about things I am pretty sure are going to happen.

For the date tomorrow there were 2 places we could of gone for the activity. He has a car and lives outside of the city, I do not have a car and live inside the city. I am also not currently working so I’m not paying extra for an Uber. Both places are exactly a 35min drive from him. I mapped it. However, one is an hour from me and the other is 20min. I told him all of this and that I obvi prefer the closer location, and yet guess which one he made a reservation at?

Now I don’t feel comfortable taking an hour subway ride at 9-10pm and god forbid he drives an extra 20min to get me home safely bc it’s inconvenient for him (a trend I’ve been noticing) so now either I spend $40 on an Uber or spend the night at his place.

If I spend the night at his place he’s going to wake me up tomorrow at 6am bc he wants to go to the gym. He and his roommates have a rule no guests can stay if ur gone so he’ll make me leave wt him. But no fucking way am I taking an hour subway ride at 6:30 in the morning. I do not feel safe riding the subway in my city late at night or early in the morning, this is not me trying to get a more comfortable ride, this is solely my feelings about my safety. I am totally ok riding the subway during more busier hours.

Ok, now this part I’ll prob get shit for because I know. I sound entitled and spoiled, but hear me out. He needs to loosen the purse strings. He is so incredibly cheap it bothers me. And he has no reason to be. He makes $100k a year, car is paid off, no loans, owns his home and charges his roommates enough to cover the full mortgage. And yet on every date he asks me for money to split it. Like you can’t pick it up once in a while? You’re fully aware I am currently not working (and for a good reason) and yet when you buy us a $11 bottle of wine you have to remind me that you paid for it 3 times and I didn’t give you $5!? Every single date he has asked me for money. I know he doesn’t have to pay for me and that he’s not obligated to but he brags about how he’s so ahead of his friends in terms with finances and his investimenti are doing so well. You can afford the $20- you don’t have to ask me for money every single time. And yea it’s cheap because we only go to super cheap or free places. He switched our date on Monday to something that was free because a $10 tkt for something that tbh is so much better was too much for him to spend.

I don’t spend money like crazy, I actually consider myself cheap as well and I budget and track my spending. I don’t shop, I rarely eat out with friends, especially right now in my life, but he is like on steroids.

Idk if I’m actually acting entitled and spoiled or if these feelings have any validation to them. (And yes he is aware of my current financial status. And yes I will be in a much better position when my job starts in 3 months)

5 comments
  1. No, I personally wouldn’t want to be with someone who didn’t take me and my situation into considerations. Your points are more than fair, and I believe most wouldn’t put up with something like this. I hope he’s worth it.

  2. I see more red flags the farther I read when it comes to money and spending time together. Not only does he not agree with anything you consider (with all due consideration), but he also has to constantly remind you about how much he spends on you every waking moment. Do you really want that for the duration of time you’re with him? That sounds like a toxic relationship waiting further down the road. If he had half a brain, he would consider driving you himself. Uber (sometimes) isn’t even safe later at night unless you’re with a few people. Hopefully you feel he’s so worth it that neither of these giant red flags bother you. I hope you know what you’re doing- for your sake.

  3. You’re unemployed dating a guy making six figures. God help me. What a disaster dating is.

    As for the dinner reservations, yes it sounds like you’re in the right on that at least. He should have picked the closer location, and he shouldn’t kick you out that early in the morning.

  4. Im letting you know now that this isn’t the sunshine and rainbows Future you want for yourself. No matter how well off he is.

  5. Yeah he doesn’t sound like a good guy.

    Maybe he’s testing you to see if you’re not a “gold digger” but he’s a fucking clown either way.

    Doesn’t care about your safety, financials etc.

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