i didn’t go on Seeking expecting anything dramatic. honestly, i think that’s why this still messes with my head a little. i wasn’t chasing some fantasy or trying to “win” sugar dating. i was tired. tired of splitting checks with men who barely liked me, tired of pretending money didn’t shape relationships anyway. Seeking felt like cutting out the dishonesty. that’s what i told myself.
when we first started talking, it felt… oddly normal. that’s the part that keeps looping in my mind.
we met on Seeking, yes, but if you stripped away the app context, it could’ve been any dating story. dinners that ran long because neither of us wanted to leave. conversations that drifted from childhood stuff to stupid opinions about movies to long pauses that felt comfortable, not awkward. no pressure. no explicit talk about arrangements. he didn’t lead with money. i didn’t ask. it felt refreshing, almost disarming.
he was older, but not in a caricature way. not flashy. not trying to prove anything. he listened. like actually listened. remembered small things. the kind of attention that makes you feel seen in a way that sneaks up on you.
our dates had a rhythm. nice restaurants, but not absurdly fancy. wine, laughter, long walks after. he always paid, but it didn’t feel like a statement. more like a habit. i didn’t question it. i liked the ease of it. i liked not thinking about my bank balance for a few hours.
at some point, gifts started appearing. subtle ones. a book i mentioned once. a scarf i’d admired in a store window. nothing screamed “transaction.” it all felt thoughtful. intentional. i remember telling myself, this is what people mean when they say sugar doesn’t have to feel gross.
then, slowly, money entered the conversation.
not directly. not cleanly. it crept in sideways.
one night, over dinner, he mentioned that his finances were a bit “temporarily tied up.” said it casually, like you’d mention bad traffic. something about funds moving between accounts, deals in progress. i nodded, didn’t think much of it. people with money talk like that sometimes. it sounded adult. boring, even.
but in the same breath, he added, “don’t worry though, i’ll still take care of you.”
i remember smiling automatically. my body reacted before my brain caught up.
take care of you.
it sounded warm. protective. reassuring. but later that night, lying in bed, the phrase replayed in my head in a way that felt… heavier. what did it actually mean? had he been taking care of me already? were the dinners that? the gifts? or was this something else we hadn’t named yet?
after that, the pattern repeated. his funds were always “about to clear.” always in motion, just out of reach. and every time he mentioned it, he paired it with reassurance. promises. future tense. once this clears, soon, i’ll make it right.
nothing bad actually happened. that’s what makes this hard to explain. there was no dramatic ask. no sudden demand. no explicit exchange laid out on the table.
instead, there was a slow emotional shift.
i noticed how often he reminded me of what he’d already done for me. not aggressively. just… factually. “after everything i’ve done for you,” said gently, during a conversation about something completely unrelated. “i just want to know we’re on the same page,” said with a smile that didn’t quite reach his eyes.
i started feeling this low-grade anxiety i couldn’t pin down. like i was behind on something, but no one had told me the deadline.
i didn’t know what i owed him. time? exclusivity? emotional availability? patience? gratitude? it was never spelled out, which somehow made it worse. if he had just said, this is what i expect, maybe i could’ve agreed or walked away cleanly.
instead, i felt myself adjusting. replying faster. being more available. canceling small plans because i didn’t want him to feel unappreciated. i caught myself thinking, he’s been so generous, the least i can do is…
that thought scared me.
because i couldn’t tell when generosity had quietly turned into leverage.
there was a moment — i can’t even tell you what triggered it — where i realized i was managing his feelings more carefully than my own. where i was measuring my reactions, my tone, my boundaries, not based on what i wanted, but on what felt “fair” given what he’d given me.
and i hated that feeling. not because he was cruel. not because he yelled or threatened or demanded. but because i felt myself slipping into a role without ever agreeing to audition for it.
i kept asking myself the same question in different forms: am i being cared for, or am i being positioned?
it’s a subtle difference. and maybe that’s why it messes with me so much. because both can feel good in the moment. both can look identical from the outside. dinners are dinners. gifts are gifts. promises sound like promises.
but inside, the weight felt different.
i didn’t end things dramatically. there was no confrontation. no big “aha” speech. things just… slowed. i pulled back. he noticed. asked if everything was okay. i said i was tired. busy. which was true, just not the whole truth.
the last time we talked, he mentioned his funds again. said they were finally moving. said he was excited to “make things right” soon. i nodded, smiled, said that sounded nice.
we never got to that “soon.”
sometimes i wonder what would’ve happened if i’d stayed. if the money would’ve eventually cleared, if everything would’ve settled into something clean and defined. maybe i walked away too early. maybe i overthought it. maybe this was just how sugar dating works and i wasn’t cut out for the ambiguity.
or maybe i caught something early that didn’t yet have a name.
i still don’t have a neat conclusion. i don’t know if he was intentionally setting up a dynamic or just repeating patterns that worked for him. i don’t know if i was being overly sensitive or appropriately cautious.
all i know is that somewhere between “i’ll take care of you” and “my funds are tied up,” i stopped feeling light.
and i’m still sitting with that feeling, trying to understand what part of it was him… and what part of it was me.
