Arrange to spend a weekend with her at a resort hotel, and let the carefree, vacation setting work its magic.
Finally, if you are not able to meet your Cuban girlfriend outside of Cuba, there is a fairly simple way for Americans to get around the rules: don't fly directly from the United States to Cuba.
Cuba doesn't generally give out travel visa to the United States except in special circumstances, and for a US citizen to travel to Cuba is a federal crime.
This is much less of a problem if you are a Cuban-American.
Even then, the internet is censored, access to websites outside of Cuba is limited, and email is monitored.
That being said, the internet is growing in popularity, especially among young Cubans.
For American guys who don't want to deal with the hassle of dating or marrying a Cuban woman, take a look at our Brazil Girls.
Cuban officials don't stamp your passport, so there will be no evidence of you having entered the country.
However, that is now the past as over the years, the number of female cigar smokers have risen.