The big sister hat is starting to give me a headache

Yet another update at the bottom...

My little sister is many thing: gorgeous, charming, kindhearted, sarcastic and feisty.

However, most important to the topic at hand is two traits in particular: naive and as stubborn as a mule.

Last night, I received a text message from her saying that she had big news she wanted to talk to me about right away.

The second she picks up the phone, her voice bubbles through the receiver.

"I'm going to the Bahamas tomorrow!"

She is near manic with excitement, talking a mile a minute, with intermittent gasps for air.

I assume she has won some sort of holiday.
Turns out I am wrong.

Navigating through her run-on sentences, I somehow manage to gather the following:
- There is a guy who comes into the restaurant she works in to paint (not as in paint the walls, but rather on canvas)
- They have spoken casually on a few occasions
- At a recent Christmas party, he mentions to her that he "conveniently" has four free tickets with a Canadian airline that expire on December 15th, and he doesn't know what he is going to do with them. She jokes that he should take her to Hawaii. He says it is a possibility.
- Yesterday, he called her to ask her out to dinner. She is already cooking, so she invites him over to her place instead. Somehow, during this dinner conversation, he reiterates his vacation offer, and they spontaneously book a flight to the Bahamas for late tonight, where they will be staying for four nights.

She calls it "the opportunity of a lifetime".
My red flags are up.

I try to glean some more information about this mysterious artist who is abound with plane tickets.
She says he is a nice guy.

I ask if they are dating.
She says not exactly.

I ask what she is planning to do for money while she is there.
She says she will figure it out when she arrives.

I ask if she has informed our parents yet.
She says it is too late to call them.

I hang up. I pace. I go over scenarios in my mind.
I call back, and tell her it would make me feel a lot better if she called my dad tonight, as he is the master of considering the practical and planning.

She is getting annoyed, as though my practicality is a betrayal, as though by not trusting this stranger, I am not trusting her, and refuses, again bringing up the "too late" excuse.

I call my parents late this morning, figuring I owe it to her to have the opportunity to speak to them first. She has yet to call them.

My mom is initially somewhat nonchalant, saying that my sister had mentioned the Hawaii idea a few days ago, and she had implicitly conveyed her approval.

I grit my teeth.
My mother has this complex whereby she feels the need to be supportive of whatever decision my sister makes, no matter how ignorant or irresponsible. She prides herself on having a genuine friendship with my sister and I, and I think she is so petrified of rupturing this friendship and the freedom of communication that she will forget to put on her mom hat at times.

I speak to my father, who thankfully is on the same page as me. He says we can't forbid her to go, because she is an adult, but when she calls them, he will be prepared to try to install as many safeguards as possible, while pretending as though I hadn't pre-warned them.
So now my parents are in action mode, trying to ascertain what information they need about where she is staying, who this guy is, how to stay in contact.

And she still hasn't even called.

***

This big sister hat seems to be velcroed to my head, as I can't stop dwelling on what reckless decision this could be.

My mom claims it is unfair to judge this guy without knowing him. Yet I can't help but wonder why such a kind and wonderful person would have no one to give a free plane ticket to except a woman he's just met, and how one could "forget" possessing such tickets until such an opportunity arose.

I know she believes in her heart that this a romantic, being swept of her feet kind of experience- yet, she doesn't even seem to be sure that she is interested in him romantically. And I can't see how a man who spontaneously flies a girl to the Caribbean is not expecting something in exchange other than good conversation.

This would all be a lot easier to swallow if I knew that she had a good radar. Yet my sister will give the most absurd men opportunities to woo her.

She is a staunch vegetarian, yet went out on a date to a shooting range with a man she describes as dense.

She says she likes older men for their stability, yet dated an insecure man 16 years older than her who had a worse job than her ex-boyfriends in their early 20s.

She was surprised when she went out for a friendly meal with a 40-year old man that he said something conveying that it was a date.

I know she generally has a good head on her shoulders, and she is an adult that needs to make her own decisions.

But I'm her big sister and I worry.

***
Update: See comment #18 for more recent details. And thank you all for being fabulous and supportive.

Update #2: More details on comment #35, assuming you are all so very fascinated.

Update #3: Continuing on my cheap rip-off of a soap opera life... I received a random phone call from my sister this evening talking about mom's Christmas present. We spoke about that for 5-10 minutes, then I mentioned that I should give her my address so she could send me a postcard (considering, to my knowledge, she was leaving that night). She then casually mentioned she was no longer going.

All the info I have is that it ended up costing too much money and it was a long story she is planning to tell me when we both had more time to talk.

I'm not really sure what to think, in all honesty.

Glad that she's not putting herself in a bad place, but also unsure if there was anything gained from all this drama. It has given me a little insight onto things, though, at the very least.

Much thanks to all the kind words of support-- glad to know that you are on the same page as me, and I'm not just paranoid!