!: “So, how much older is he than you?”

$: “Sixteen years.”

!: “That’s kinda crazy, no? I mean, he’s closer to qualifying for AARP benefits than he is to you in age.”

$: “So what if he’s a tiny bit older than me.”

!: “Tiny bit older than you? There were like four presidential terms between the time that you and him were born.”

$: “Whatever. It’s not a serious relationship anyways. I just want something casual, you know? I just want to have a fancy dinner every once in a while and have some nice conversation without thinking that something has to happen right away.”

!: “I get that, but you don’t want something casual with someone who’s a little bit closer to your age? What about Brad? I thought you guys had a thing.”

$: “Yeah we did for a little bit, but I felt like it never really went anywhere. I was the one who was always initiating everything. Remember that time we went to that restaurant with that floating noodle bar that I wanted to go to?”

!: “Oh my god, yeah, it looked so good.”

$: “Well, I had texted him about wanting to go there for the longest time and he was like ‘Oh cool!’…Nothing more after that. No ‘Should we go?’ or ‘When do you want to go?”, so I just booked the restaurant and asked him if he wanted to go, and he just said ‘Yeah, can’t wait.’ And, we did end up going, and it was fine, like we had a good conversation and the food was really good, but I just felt a little bit underwhelmed. I asked you to go to this restaurant with me, and I planned everything. You can’t just show up and be ‘okay’ and expect me to keep caring about you, right?”

!: “Yeah, that’s a little bit disappointing.”

$: “I was so frustrated. I felt like I was performing the entire time for someone I only kinda knew. Like it would be better if I didn’t know him at all, or if I knew him really well. It’s super awkward when you kinda know someone, but not well enough to know if you can say certain things around them. I was just annoyed with the whole thing.”

!: “Okay, so then why do you want to spend more time with this new older guy then? You’re kind of performing for him too, if you think about it. I’m sure you like him somewhat, but not enough to want to date him seriously, so you’re stringing him along for meals and fun, and you might be hurting someone’s feelings in the end.”

$: “I don’t know, I guess this guy just feels more low stakes for me. I know it’s mean, but when I get tired of it, I could always just say that he’s too old for me and then back out. Obviously, I don’t want to hurt anyone’s feelings, but it’s also not my job to think about what he wants at this point in our relationship.”

!: “I feel like you’re resentful of the fact that your previous relationships didn’t work out the way you wanted them too, so you feel like you’re entitled to act how ever you want towards this guy as ‘payback’ for what you had to go through. I like that you’re getting to go out to nice restaurants with this new guy, but I also feel like you’re too good of a person to be doing this to yourself.”

$: “It’s not that serious. I told him I didn’t want anything super official right now, and that I just wanted to hang out and keep things casual. Come on. Tell me you wouldn’t do something like that if you were single and not looking to get into anything serious? It’s fun!”

!: “I don’t know. I mean, yeah, ideally it would be nice to have someone pay for a really nice meal whenever I want, without expecting anything in return, but that’s not reality. He’s probably thinking he’s playing the long game with you, or that eventually you’re going to want something more serious with him.”

$: “You think that at his age, he’s going to be playing the long game?”

!: “Well, you never said he was smart, just that he had money to take you out on dates. Besides, if someone is that old dating someone much younger than them, I think there has to be something wrong with them. Why can’t they just date someone their own age? Why would they date someone so much younger than them? I mean I have trouble even thinking about dating someone who is even 5 or 6 years younger than me. I can’t imagine dating someone 16 years younger than me. I know some people say that age is just a number, but it really isn’t there is a lot of experiences people can have in those 16 years that make you different from someone younger than you.”

$: “I get that but I think you’re misunderstanding what this relationship is. It’s just a casual, fun thing. I told him I wanted something casual and fun. I joke about the fact that I don’t like paying for dinners, and he was happy to pay for all of them. I don’t think it’s that big of a deal at the end of the day. Who cares if he ends up catching feelings?”

!: “What if you end up catching feelings? Honestly, that’s the part that worries me the most. What if you, for some weird reason, end up catching feelings for this man, and end up pursuing an actual relationship with him? I feel like the more you spend time with someone, the more you’re likely to develop some sort of attraction to them, and I would honestly hate to see that.”

$: “Why?”

!: “I just think you’re too good to be married to someone that’s that much older than you.”

$: “How flattering. Thank you.”

!: “Yeah, if you’re going to get married to someone older than you, they better have more than ‘Let me take you out to dinner on my dime’ money. They better have ‘I don’t want you to live in a small apartment, so let me buy you and your friend each a house’ kind of money.”

$: “Wait, why are they buying you a house?”

!: “If they’re going to be rich enough to let you live a soft life, then they better do the same for me. It’s only fair.”

$: “Wow, I thought you were all about ‘real relationships’ and not dating people simply for their money.”

!: “I’m not, but that doesn’t mean I can’t take advantage of a friend that does.”

$: *rolls eyes*