this part of your reply to @Willow_Wisp is key: “...I’ve thought about stopping talking to this person a few times, which isn’t good. And yeah, I have tried to tell them everything and they simply won’t listen and get defensive. Then demands I end the conversation. I’m growing very irritated and confused to the point where I might actually distance myself and make a good “clean break.”
This person is manipulative and gaslighting, causing you to doubt yourself. You know what you need to do. Good luck!

Run. You've got an abuser.
If you don't have this book you should buy it and read it.
From "the abuser's handbook by Dina McMillan.

"Start taking care of her. If you can afford it, buy her things or pay her bills. If money cannot be spared, do things around her house to improve her living situation (this can be as simple as taking out the trash). Let her see that her life will improve if you are in it."

'Note: if she indicates discomfort or disagreement with anything you are saying or doing encourage her to see things from your perspective. Then explain what you said or did in a way that seems harmless or driven by passion (discussed in detail in the next chapter). Use the right terms — linked with masculinity or romance — and she will probably stop criticising. If that doesn’t work another approach is to tell her she is being ‘overly sensitive’, ‘judgmental’, ‘cruel’, ‘racist’ or ‘unfair’. Women hate to think of themselves this way, so your accusation will put her on the defensive. She will then get distracted trying to prove she is not any of those things and her focus on what you did will be lost."

He's insecure and trying to impress you by giving you what he thinks you want.
It is manipulation, but he doesn't really know it, he's just desperate for some security that the relationship is strong. Men are intrinsically transactional, they're taught to be by media every day.
If he can learn to stop that he'd probably be a devoted partner, but warning, the same media that taught him to be manipulative also taught him to be aggressive, if so no compromise end the relationship.

This sounds like the traits of an abuser. If his desire to help you were true, it would have came without contingency. And if the offer was only valid during a secure relationship, he would have reserved giving it until it was. Not by trying to bait you with a dangled carrot. I think your intuition was spot on.

Seems like most everyone is going one way on this, so I'll give a possible taste of the flip side of the coin. We weren't there to hear how things were said, so we're all taking stabs in the dark anyway.
Long term investments in a future can only be realized if there's a future. Perhaps it wasn't a bribe so much as a statement of willingness to be fully invested and committed. Even without a partner I'd be willing to state if I were in a long term relationship I'd help them with something like that. It's possible it was meant the same way someone might be willing to have a baby if their partner would marry them (or vice versa). Move in together if they were engaged. There are probably tons of examples of conditional things like that that aren't bribes necessarily. Try to figure out how it was said/meant from context and assessment. We are missing a lot of that info.

Well, the Sugar Daddy thing is a thing .... but usually isn't considered a "serious" relationship. So I don't think that is what is going on here.

But, no you aren't crazy to question it and the way it was presented does sound like bribery of sorts. I can imagine several motives for the conversation you describe. Most of them involve a sincere desire to be in a relationship with you, but yes, the way it was presented was premature, awkward, inept and inappropriate, which should amount to at least a minor "red flag" on this person's self esteem and emotional stability..... not something to avoid them over, but just kind of a "watch for more scary clues" just in case.

I think the "correct" or "appropriate" back drop for this conversation would have been if you were already in a serious relationship and this person wanted to do that as a way to invest in you and the relationship.

Perhaps it was presented in the context (in his mind) where "you" was not specifically YOU, but a "you" that would be a (any) hypothetical partner?

Since you apparently have no current plans or desire to make this a "serious" relationship. I think the best thing to do is to make that clear. Or you can plainly state you don't think such a consideration is appropriate for this stage of your relationship.

Then just brush it off as one of those awkward, inappropriate comments we all make from time to time. ..... "Least said, soonest mended" sort of thing.

You did right.

That is not the sort of question that should be asked in any casual relationship.

My wife and I were already married for 4 years before she went to university.

I'm seeing red flags all over.

Check please.

It seems to be some form of bribery and insecurity on the part of the person who made the unsolicited offer. I wonder what is in it for him? How are you going to repay him for such generosity, in kind?

Possible scenarios if you live with him might include spying on you and looking at your phone to see who you have been chatting with or calling. Asking where you have been if you arrive home late and imposing restrictions on your personal sense of freedom.

If someone really wants to help you in some way then he or she will do so without imposing conditions as you described. It sounds like an unsavory business proposal.

I'd definitely give that one a wide berth....

As to the first part about offering to help, it could be taken more than one way depending on the wording. However, always go with you first gut instinct. That is your subconscious throwing down a red flag.

As to the big dramatic defensive act... just another red flag. Time to move on, they want to buy your commitment for which they will never let you forget it. No. Don't go there.

IMO, this is obviously an attempt at bribery and he appears to be asking for your body for the money for your education. The mere idea that the only way you would get help is if you're in a "serious relationship" implies a debt on your part to him and the payment is your emotional and sexual focus being him. I mean, what happens if you are obviously not happy in the relationship? Does that mean that he no longer helps? Where does that leave you?

I'm not even going to get into how controlling it is to even want such a scenario. Sounds a lot like an impoverished eastern European girl attempting to escape to America and has to marry some guy for it to happen.

Some men view women as 'objects' that can be bribed.

“Good question. I don’t have an answer for that.”
Not anything? I would hope that someone making such a significant statement could reflect on it and come up with something... even a bad answer.

Am I right in thinking by "further your education" he or you mean pay for it? Or is this like a superior in school and they are offering to curry favor or good grades for you?

Assuming it is payment I would say personally I would not pay for someone else's education (and I have done that) unless either the amount was trivial to me, or we had some strong familiar, friendship, or other relationship. However to mention this in a way that's coercive or suggestive - that's out and out creepy.

Overall I think it is best to keep money, "gifts", and "favors" out of friendships. In a relationship I think it is twice as bad.

If someone genuinely wants to help, they don't need collateral. You did right.

Of course it does seem off. The dude is insecure to say the least, never a good sign to develop into a more serious relationship, regardless if he does it for any reason whatsoever. Some men will push for a commitment right after they've started dating you. This is a huge red flag, when men push for commitment prematurely, it signals not only that they're insecure, but that they also have low emotional intelligence. Essentially, insecure men are trying to "lock you down" before you begin to notice their flaws.

Definitely psychological bribery. Keep away.

Typically if humans get overly defensive you hit to close to the truth than they liked.

Money is a tricky subject for many people, I know people in long term relationships and marriages that have felt they helped their partner by supporting them while they studied and it has been a sacrifice for them. Talking about money can be really stressful, and people’s responses may come across a lot stronger than they realise

Even if the guy’s rich; helping someone do a course they want is an investment in them, they will hopefully do well and feel good about the choices it gives them. To do this for someone they’re not in a serious relationship with would be an act of charity and put them in a position that an established relationship would be harder to achieve due to the power play already existing by them acting as a financier to their aspirations.

I’m guessing the comment was in context here, and you actually said that you’d like to study further?

I have an ex who tried to bribe me with trips, the Northern Lights, Disney Animal Kingdom Lodge, but none of it would make me stay once he got unreasonable. I would have loved to stay friends, that’s the bit I missed about the relationship, but that’s life.

It's hard out there. Most people are insecure. If it's not a pattern, then this could be an opportunity for you to see if this is a relationship you want to pursue. If so, could the incident be a jumping off point to talk about how things are going? Sounds like they came back around and admitted they weren't sure of their own intention. So that's promising.

IF this type of thing is a pattern -- Especially the defensiveness -- bye, boy! IMHO, it's the extreme defensiveness that's the reddest flag.

I was seeing a really great single dad who was very insecure for physical reasons. He did a similar thing with me 2 months into our relationship, but about buying "us" a 200 acre farm. "Wouldn't you like that?"

Um, I already own a house and they're a lot of work and 200 acres, holy crap, no! I would like to continue to enjoy getting to know you! But he had to leave the condo he was renting, wanted to buy and wanted me to move in with him. I'm sure it wasn't intentionally paternalistic or caretaking or codependent, but... behavior doesn't have to be intentional to be harmful.

I withdrew, because I wanted him to do what he needed to do for the next step for him and his son without me being responsible for that step. If he or I had just said, "I'm scared about making such a big decision because I like you and it's odd timing," then we could have had a conversation to grow us closer. NEither of us were there at that time. I do hope they're happy wherever they are!

As if sex and relationships aren't transactional? Love happens occasionally, but transactions still continue. Is it being romantic, naive, or boredom to post this?

I see a couple of ways you can work this.

Like most everyone who's already responded, I agree, dump him. Manipulative, immature, not long-term material. This is the easiest, probably best, and most conventional path.

Here's another option to consider. Only consider it if you have the intellect and emotional maturity to do so. How? Let him pay for your education. You've already figured out he's not a long-term option, but you have a life to get established. What's the likelihood that you will meet "the one" while you are focusing on your education? More likely, you'll date a few guys who are just "meh." This guy is that, but he is willing to pay for the privilege. Turn him into an unwitting sugar daddy, and when you are done with him, dump him and move on.

Yeah, I know, ruthless. But he started the game. Rather than get yourself tied up in "what should I do" knots, flip it on him. The next move is yours.

What are you going to do?