The original post makes explicit that the so-called contract (unilaterally sent text messages) was created after most or all of the gifts were already given. How many times does it need to be said? Once the giving of a gift is completed, you can't reinvent a gift as a loan.
All the completed gifts? Still gifts. The "agreement to be a better friend" doesn't change the past.Quoting melon123
All the new gifts made without condition? Unconditional gifts.Quoting melon123
Also, the words you use to characterize your actions do matter. If you call something a gift, a court is going to take you at your word that it was a gift. You can try to argue that although you said "gift" you meant "loan", and that both parties understood "gift" to mean "loan", but unless you have a written contract containing such a definition I would expect a court to find that argument to be laughable - and if you do have a contract defining "gift" as "loan" you're likely to inspire the court to wonder if your goal in redefiining the terms was to confuse the other party. You may be able to argue that particular transactions took the form of conditional gifts, based upon the full facts and circumstances of each specific transaction, but you cannot recharacterize a completed gift as a loan or impose conditions after-the-fact.
In terms of the language of the so-called contract,
Assuming that there was a gift of money associated with that text message - not past gifts, but a new, current gift. As previously noted, the "contract" is fundamentally flawed, as all gifts remain gifts. It doesn't say, "The money is a loan that shall be forgiven if certain conditions are met," or "The money is a gift only if the following conditions are met." Ambiguities in a contract are interpreted in a manner favorable to the party that did not draft the terms.Quoting melon123
But let's suppose for the moment that a court would read the tortured language as creating a conditional gift in relation to the transaction associated with the text message - the problem remains that a text message does not create a contract. Contracts require offer, acceptance, mutuality and consideration - If I send you a text message that says, "If you won't be my BFF you have to pay be $1mm," it has no legal significance. If I make a gift then send a text message attempting to make that specific gift conditional, too late. If I send the text message before making the gift, I need to show that it was received and reviewed prior to the making of the gift and that its terms were accepted.
Further, the definitions proposed create more problems for poor melon123,
If that is a theoretical statement, it betrays the fact that the so-called "contract" does not support the redefinition of gifts. But if it is what the "contract" provides, a "gift" refers to a "loan" that by its terms will be forgiven, and any "loan" must be "paid back fully within 2 weeks of given date unless otherwise stated". Absent a statement with each new "gift" that it the money given is not to be repaid within two weeks, the recipient has a strong argument that the conditions are removed and the gift vests if the gift is not recalled within the described two week period.Quoting melon123
Also, as jk has intimated, the conditions are dubious - that she "be a better friend, keep him happy (as defined by him), that she  not ignore him, that if she ever lies about anything or skews things (as defined by him)..." That seems like another way of saying, "You have to be my girlfriend, you have to be here when I want you, and you have to put out" - conditions that range from the type a court is unlikely to enforce to the type a court will not enforce.