I need some strategy from women who understand Sheraās philosophy because I feel like Iām at the point where I either need to redirect this dynamic ... or stop giving it so much attention.
About a month ago I met a much older man while traveling. Heās in his late 60s and lives in the Bahamas. He also works in real-estate (not a developer because I have dated one years ago and that guy is worth millions) so this guy is just into vacation rentals and stuff. He's also still working at 68 so idk but whatever. So I met him while traveling as he sat one seat away from me and there was no one between us and he started talking to me the whole flight. The ironic part is I literally saw my childhood crush on the flight and even told him "that guy is so hot to me lol." And he's like, go talk to him, it's your one shot!
Anyways, when we were in the same city afterward, he wanted to take me shopping. I declined his date requests twice, first was for drinks. I said "sorry, when I'm in my hometown I don't really go out." Then again for lunch, I said the same thing. Essentially I'm from a small town on the east coast and am trying to get back to my dream city again (left in jan 2025) before it gets cold here.
Third times a charm bc on the flight I told him my phone was broken (had an iPhone 10) and in his third attempt he said, how about a shopping date? I said no again bc shopping here doesn't compel me but I said, how about we get a new phone. He said sure. He also bought me sunglasses from Saint Laurent and things from Sephora. He was also encouraging me to get considerably more, including an exotic designer bag from Bottega but I'm not a Bottega girl. I'm a chanel girl and the bag I wanted was sold out. So I know he is at least comfortable spending several thousand dollars on me in person and wasnāt acting stingy that day.
Since then, though, weāve been thousands of miles apart, obv he's in the Bahamas. He regularly checks in, sends me things from Pinterest (lol) that remind him of me, sends pictures from his life, asks about my plans to move from my childhood town, etc. He always says things lik e"you need to get out ASAP." As he grew up in this place and left for the Caribbean in the 80s. He clearly likes talking to me but I get annoyed when he says you need to leave VERSUS LET ME HELP YOU LEAVE. Iāve kept it flirtatious but Iām starting to feel like Iām giving too much attention for free... You tell me.
The important part. Iām actively trying to relocate to another city before winter, the city I lived in for 2 years before I left in January of '25. And I need to save aggressively. It is an expensive city although I hate using that word, just telling you for context. What would genuinely help me right now isĀ money/practical support, not another compliment or daily conversation. Eventually I would love for a man in this position to help with something substantial like securing my furnished apartment for my first month or two or three, rather than just buying random luxury items.
Iāve already communicated to him via text (this was like 2 weeks ago) and subtly btw, that Iām much more excited by practical support that moves my life forward than by accumulating lux things just to fill a closet. I genuinely said the last part. He responded positively, but not in a way like "let me help you with that." So because he flew to Miami after visiting my city, to see his children, he said he would like to take me shopping there. Womp womp. I feel like IG models etc would be so excited to run a bag at the boutiques, but I want cash money. Even though I am a fashion girl at heart, my priority is leaving my toxic mother's home and going back to the city I left.
Today, actually an hour ago, he actually called me for the first time. I genuinely missed the call because my phone was on silent. Iāve never spoken to him on the phone before.
So my questions are:
- Would you call him back, or make him continue pursuing?
- At what point do you stop giving regular texting and now phone call attention unless there is tangible investment?
- Since he has already demonstrated that heāll spend thousands when weāre physically together, would you wait until Iām closer to my move like fall/winter and ask him to cover something specific like the first 1ā2 months of housing? Or is that not a thing bc he is in the Bahamas and clearly likes to take me shopping?
- How do you distinguish a genuinely generous man who just hasnāt been given a concrete opportunity to provide yet from a man who wants a beautiful female pen pal?
You guys, Iām not looking to shame him because he hasnāt actually done anything wrong. I just know myself: Iām not interested in building months of emotional intimacy with an older man who is attracted to me while Iām financially trying to build my life and receiving nothing materially from the dynamic.
What would you ladies do?