Playing It Safe
If you are going to connect with someone overseas and you are going to send money, follow these steps to protect yourself.
1. Always buy plane tickets yourself in the person's name - that way they cannot scam you. They also can't get a refund. Always tell them you are doing this. A real person will be very happy you are doing this. A scammer will try to talk you out if buying it, they will want you to send the money.
2. If they need money for an emergency, such as a hospital. Contact your embassy in the country to confirm the Hospital's contact information. This is what Consuls do, they help their citizens with problems in local countries.
3. Always suggest that you will send the money TO your country's embassy in that country, and they can pick it up there. Of course a scammer will try to talk you out of it, because they know they can't touch it. If they are ok with that method, you can probably be ok sending it MoneyGram or Western Union.
This will not help you with real scammers, such as Filipinos who use their real identity, but it will both the total fakes.
4. The most important things for your is to decide up front, how much are you willing to lose if it is a scammer? Make a real decision, and stick to it. If you are using your judgment and believe the person, that is your decision. Then set an amount in your head.
5. Always send less than they ask. If you are asked for $500, tell them you can only send $50 - watch the reaction and what they say to this. A real person will be either grateful or slightly paniced. If the person is just so so, watch out, because it must not have been that important after all - such as you are being scammed.