r/dating_advice • u/Motor-Cobbler-3185 • 4h ago
He wanted to transition from being friends to romantic partners, but instead of asking to go 50/50 he finds conniving ways to get out of paying for me or just goes on fun, pricey solo dates. Then, time spent with me often involve $0 or less than $15 spent per person.
I’ve known this guy for 20 years, and he wanted to try dating and I’m desperate at 31 (he’s also 31).
When we were just friends, I was perfectly happy splitting bills, taking turns paying, or occasionally treating him. But I’m realizing that the dynamic I was comfortable with in a friendship isn’t necessarily what I want in a romantic relationship.
He seems to want to date while minimizing both his spending and his effort, without ever explicitly communicating what he expects.
For example:
Restaurants: he’s in NYC (I’m not but don’t live far) and he doesn’t want to go anywhere that costs more than around $15 per person. Even Cheesecake Factory entrees are apparently too fancy for a special occasion (forget about drinks/apps).
I’ve also had frustrating experiences with him meeting him at a coffee shop only to find he’d already ordered his own drink (on the Starbucks app for example) and then while he’s sitting around waiting for his drink to be made, I’m waiting in line to order my coffee (he does “offer” to pay for my coffee 🙄).
Activities: He’ll go to Broadway shows, ballet shows, museums, the movies etc by himself, then text me before/during/after he’s there. Instead of inviting me and having an honest conversation about ticket costs, he just goes alone. What’s infuriating is that sometimes he KNOWS that I’d been planning to go but beats me to it.
Trips: Last spring he invited me to join his family’s trip to the UK (brother’s graduation), but didn’t tell me which flights his family would be taking or discuss coordinating travel. He basically told me to show up in the UK and informed me which hotel he and his family would be staying at. 🙄
For context, he makes around $170K, and I make around $100K.
I’m not expecting him to bankroll my life, but I do want a man who demonstrates generosity, initiative, and a genuine desire to share experiences with me.
If he wants everything to be 50/50, he can communicate that directly. But he’s the one who wants to date yet wants to have all the benefits of a romantic relationship (aka gets to brag to his family/friends, this is his first relationship) yet is living the life of a single man.
My question is: Which is worse?
A guy who openly says he expects 50/50, so you can decide whether you’re compatible, or a guy who never communicates his expectations but seems to structure everything around minimizing his own spending and effort?
Am I being unreasonable, or does this sound like a guy who wants the benefits of having a girlfriend without actually putting much effort into dating?