he cant
NO. It's illegal. It's as illegal as someone over sixteen selling drugs.
Asylum- but only if filed within 1 year of entry into the U.S.- otherwise no.
He wouldn't want to leave the country and have his papers checked, he might not be allowed back. And marriage does not change the status of an illegal immigrant.
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I'm assuming you mean an illegal alien. This is a topic for an immigration attorney, because since you entered the country illegal (without documentation/visa) you're subject to deportation. Using an American citizen to seek citizenship only applies to marriages and the work place, meaning that simply living with an US citizen does not make you eligible to stay.
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It is not illegal for them to date, but is is illegal for them to have sex.
No, it is not illegal for a 14 year old and a 17 year old to date. It is illegal for them to have sexual relations.
No, but it is illegal for them to... do things.