Poor woman's rich friend has been anonymously giving her financial help. Sweet or controlling?

Okay, it’s hypo time. It’s long before I freewrote it and am too lazy to edit. No poll because I can’t 'be arsed. Today’s story is about Lily, an artist, waitress, and college student in her late twenties. Despite being pretty, charming, and clever, Lily doesn’t have two nickles to rub together. She grew up in an upper-middle class family but left home at age 15 to escape her mother’s passivity and her father’s fists. Living on her own, she worked hard and saved a nice bit of change. Unfortunately, she also dated a series of guy whose resemblance to her father everyone but her could see, culminating in a marriage at 23, to a man who sent her to the ER four times in one year. By the time she divorced him, he had not only depleted her savings but ruined her credit. As you might imagne, she is less than confident of her taste in men.

Three years ago, Lily he met Edward–a handsome, charming regular at the coffeehouse where she works. She was flattered by his amorous attentions but reluctant to return them. Edward, surprisingly, seemed perfectly willing to be platonic. What had drawn his attention to Lily was a painting of hers on display at the coffee house; he’d been coming their for months but never been anything but polite to her until the day he asked her who had painted “Eurydice Fades,” and when she said it was her, suddenly got very interested. He bought the painting on the spot, and over time they became close friends.

Now Ed’s got money. He doesn’t throw it around, and when he was just her customer Lily didn’t realize that; but as their friendship deepened she realized it was in the hundreds of millions–family money to which Ed is the sole heir. Though he could easily be idle, Ed works as a lawyer; his practice consists entirely of pro-bono cases, representing criminal defendants who can’t afford lawyers, or immigrants seeking asylum, and so forth. Lily has met many of Ed’s peers and colleagues, and no one has a bad word to say about him–except, that is, for his ex-wife, Anna, who considers him a controlling asshole, though a very subtle one. Anna doesn’t claim Ed was physically or verbally abusive, but she speaks as affectionately of him as Lily does of the two men who between them broke both her ribs. Lily has long classified Anna’s opinion of Ed as null information.

Lily’s life has gotten a lot better since she and Ed became buddies. She got a rent-controlled apartment in a wonderful building (that happens to be within walking distance of Ed’s even more luxurious one); she got a full scholarship to a prestigious university (that happens to be Ed’s alma mater); and she’s sold a ton of paintings to a variety of people. As mentioned above, Ed never pressed Lily to make their relationship physical. This let her grow to trust him more and more, and a couple of weeks ago she decided she loved him, told him so, and with him made that famous two-backed beast.

Which brings us to our dilemma. Lily’s graduation is coming up. In a meeting with her academic advisor, Lily mentioned a friend of hers whom she hoped would get the scholarship after her. The professor laughed. Ed has been funding the scholarship anonymously, he said; it didn’t exist before Lily got it and probably will be discontinued afterward. The professor is only spilling the beans because he’s retiring and no longer gives a fuck – unless Lily, he says, who clearly gives quite a few fucks.

Lily is as disturbed by this revelation as by the insults. Doing a little digging, she discovers that her apartment is so cheap because Ed is subsidizing her rent, and that he’s been buying her paintings through proxies. By the time she confronts Ed, she is furious. Presented with her evidence, he admits t everything. “But I wasn’t trying to hurt you, or even control you,” he says. “I was trying to help you. I love you. I loved your paintings before I knew you had painted them. I wanted to help you, but you wouldn’t take my money directly, so I had to be discreet. I swear I am not trying to fuck with your head. Please forgive me.”

Lily isn’t sure she can. Ed’s confession makes her question every moment of their relationship in both its platonic and romantic phases. Every time she looks at Ed, she thinks of Anna’s assessment of his character; every time she looks at herself, she wonders how many people at her university know about her scholarship, and whether they all think she earned it on her knees. But she also can’t help but recall how sweet and patient Ed is to her, how generous to everyone.

Is Lily right to mistrust Ed, or are her suspicions correct?

I’ve always found the “I was secretly supporting you” plotline in fiction to insulting and deceitful at best and horrendously manipulative and disturbing (in addition to insulting and deceitful) at worst (and yes, that includes when it’s an estranged relative pulling the strings), so I say she should run far, far away and never interact with him again.

So Ed’s been secret sugar daddy for Lilly. That’s a little creepy, and enough to make the spider sense go all tingly. Maybe he’s a good guy, maybe he’s a serial killer. Hard to say.

In any event, Lily needs to decide how she feels about being bought and paid for by Ed. If she’s cool with it, she might get a nice life of affluence or she might end up with her severed limbs stuffed in a dumpster.

If she’s not down with it, she’s somewhat better off than she was when she met Ed, and she’s free to walk away. Of course, if he’s vindictive about it, there’s still the severed limbs in a dumpster as a possible outcome.

Does Lily have some sort of intellectual disability? It seems that someone with at an at least room temperature IQ would have their suspicions that their financial outlook markedly improved after meeting someone that rich. Okay, maybe she wouldn’t necessarily figure he was buying paintings via a proxy, but a normal person would at least wonder if it wasn’t someone he knew with a similar net worth buying them because he put them up to it.

Anyway, I guess it’s a bit creepy and controlling but she’s had her head in the sand if this shocks her, and has implicitly agreed that it was okay if she isn’t as shocked as she claims.

Lily needs to ask herself how she would feel and have felt if Ed had supported her openly. I will, however, point out though that Ed has lied:

From your story, Ed never asked.

Funnily enough, some years ago I considered financially helping out someone I knew. To a very much lesser degree than Ed, of course. I would have done it anonymously because I didn’t want them to feel indebted to me. Then they severely disappointed me so I did not follow through - and they are no longer part of my life - and then the window of opportunity passed.

Also, there’s an advert which ran recently on UK TV where the clients of a hairdresser club together to fund the education of the hairdresser’s daughter and she invites them to her fashion show.

The fact that Ed wasn’t more up front about what he was doing is definitely a big red warning flag.

However, I do not see that he’s being controlling, as the title of the thread suggests. Controlling would be him making her take the scholarship, or him threatening to cancel the apartment if she doesn’t do X. He hasn’t done any of that stuff as far as we know.

Phrased the right way, he could even justify what he’s done. After all, his whole career is built around helping people who need it. If he’d kept it all secret so that she wouldn’t feel obligated to return his affections, that would even be a point in his favor… which is why it’s curious that he didn’t explain himself in those terms. His explanation in the OP sounds more creepy stalker to me - “I loved you so I lied about all this stuff” is totally different from “I wanted to do all this stuff, but not have it affect your feelings about me.” It’s a fine point in meaning, but I think each version speaks to different underlying motivations.

Were I Lily, I’d definitely slow down the relationship and give myself some time to think about how I feel about each thing - individually and collectively. There’s nothing inherently wrong with being supported by a wealthy significant other, but she has to decide how she feels about it.

She certainly has to factor in his ability and willingness to create all kinds of fake fronts and proxies, and she probably need to re-asses everything she thinks she knows. For example, all those people who said nice things about him: are they genuine, or are they like the fake names he bought artwork with and the fake lease her apartment is under? Lots of people will say nice things about you if you donate to their cause, hire their firm for work, defend them in court for free, etc. In part, this might come down to how subtle he really is. Like, the scholarship was obviously not set up in a sophisticated way - no shell companies, fake charities, etc. If he’s new at this deception, that’s a good thing in his favor.

Eh, I guess I’m too old and broke to care much. I’m also inclined to think the best of people absent a whole lot of incontrovertible proof to the contrary. I ain’t got time for games, not even the mind games I play with myself. Do I love him? Does he love me? Fine, let’s get hitched.

I’d be a bit taken aback, but really, at the end of the day, what’s the problem? He went out of his way to NOT be controlling. “See, I had to break up with this guy because he was too nice…”? Weak.

One thing you seem not to be considering is the damage to Lily’s reputation. The rent subsidy and phony scholarship (especially the latter) have surely caused those who know about them to think Lily is either a kept woman or a manipulative bitch. Obviously the scholarship secret wasn’t kept ( there’s no reason Edward would have told the professor); half the faculty may now. Her teachers probably don’t respect her, and that may have subtle but grave consequences later.

Consequences? She’s got a kind, generous multi hundred millionaire in her life. She can do whatever the fuck she wants.

Yeah, you’re right. I’ve devoted a lot of my time and energy to learning to ignore reputation, and focusing on work instead. The reputation follows from the work I do.

More than one successful artist has been a kept partner. More than one successful artist has gotten there *actually *on their knees, not just in rumor. Eventually, you’re as good as you can convince people you are as an artist. (Which, if he was the only one buying her artwork, she may not be very good after all. I think that’s the part that wound sting me the worst, thinking I was getting the hang of this art thing and then finding out I really had only one big fan.)

If she didn’t go to school for art (or academia), it’s unlikely her teachers’ opinions will have great weight. If she’s got a degree, it’s as good as any other.

Well, the OP doesn’t specify what the degree is in. On purpose. But what I was thinking about is humiliation. The professor basically called Lily a whore to her face, and I doubt he’s unique in that assessment. Some people would not care about that, true, but some would. For Edward to expose her to such a risk, sans her consent, is very disturbing.

It’s a mess. Edward should now step away. Lily should be grateful. Anna should shut the hell up.

Ed sounds like a genuine nice guy (the pro bono law work, especially) so I’d be inclined to give him the benefit of the doubt - it seems true to me that he would have been willing to keep supporting her even if he wasn’t getting any direct benefit. To me, it comes down to whether she genuinely likes him as a friend, and whether the sex is good. Everything else is irrelevant.

Reputation’s one thing, but I’ve yet to meet an artist where a bad reputation was hindrance not a benefit.

And if *I *were Ed, that professor would be discovering retirement is no insulation against the consequences of one’s spiteful actions. Hundreds of millions and a law degree can afford one quite a vast degree of fuck-you…

She never was forced to have sex with that man. She could have just kept it in the friends zone.

This is a weird one for sure.

Ed is, of course, absolutely being extremely controlling. He has created enormous changes in Lily’s life. Lily didn’t and couldn’t consent, if only because she didn’t know. Until this point it has not felt controlling because he hasn’t done anything she knew she disliked at the time, but that is only a misperception on Lily’s part because she was missing the information that Ed was behind all this.

As to what Lily should do, well, it’s possible Ed will continue to have entirely pleasant effects on Lily’s life. But we all see huge red flags all over this thing, and Lily’s in pretty uncharted waters here, trying to steer her life to turn out so that she likes it. At best, she has a generous but bizarrely dishonest and manipulative “wild card” character substantially controlling her life.

I’d advise Lily to lay groundwork by telling a wide variety of trustworthy people what has happened, and then extricate herself as quickly as carefully possible.

Unless Lily what? Did you mean “unlike Lily”?

Anyways, I certainly find it creepy, because Ed obviously had romantic intentions from the get-go… because of that it seems like there’s a master plan, rather than just a free no-strings-attached gift. Does Ed keep paying for everything if she dumps him?

I would never expect the circumstances behind a scholarship to be known to the professor, were I Edward. Seriously, how does that happen? None of my teachers ever had a clue how I was paying for my classes.

My academic advisor did, but it was because I knew her before college thru one of my high school teachers. But my point is that Edward had to set up this scholarship and make sure Lily won it, and that’s the sort of thing that gets gossipped about.

Which A gues against this all being an evil plan to get into Lily’s pants, by the way. A schemer would have been more devious and discreet.

On re-reading the OP, it’s the buying of her paintings by proxy that most concerns me. Anonymously supporting education and housing is one thing, but the paintings thing is an actual act of deception.

Indeed, and waiting 3-4 years means he must have had a colossal case of blue balls.

I’m in academia, and I would be surprised if Lily’s professors gave a damn who was paying for her education.

I think it’s unlikely that her advisor would have any way of knowing who was responsible for Lily’s scholarship, for bureaucratic reasons (this would presumably be handled by the financial aid office, not the academic department) if not confidentiality ones. This is well outside my area, but I’m not sure it would even be legal for someone in financial aid to blab to a student’s instructors that her tuition was being paid by a wealthy friend.

Again though, I don’t think this would make any difference to most professors. The college must have other students whose education is being wholly paid for by their wealthy parents, so it’s not like Lily is unusual in not paying her own way. If her professors don’t feel her work is up to par they’re free to give her the grades they feel she deserves.

The department has more to worry about than Lily, as her advisor’s behavior has given her grounds for a sexual harassment complaint.