As President Obama’s last year in office creeps towards the finish line, the United States’ first African American president is eagerly flirting with the history books.

Last December, President Obama opened up executive relations with Cuba for the first time in decades. Now, he wants to take this new relationship to the next level. The Obama administration is not quite ready to jump into bed with Raul Castro, but they are at least going out to some fine dinners.

Indeed, at the Panama Summit last week all of Latin America got to witness something remarkable. The U.S. and Cuban presidents were giggling together while symbolically joining our nation’s hands with the goal of cooperation and peace. However the specifics of this lovey-dovey agreement are grounded in some serious issues, including the War on Terror.

The Obama administration has made it clear that Castro needs to start implementing some policy addressing both the freedom of the press and human rights. In exchange President Obama has agreed that Cuba will be removed from the list of state sponsors of terrorism. In fact, according to Al Jazeera, our State Department has finally finished its lengthy review on this issue. While the president can exercise his executive powers to remove Cuba from such a list, he still needs congressional support to lift the trade embargo.

According to the Washington Post, Republicans have criticized Obama for the last few weeks because they believe that opening relations with Cuba will only help them support terrorism. However, if we truly wish to stop the spread of terrorism in Latin America, shouldn’t we employ tactics of engagement? If we are able to have open discussions between our executive branches, then we will be closer to solving our issues diplomatically instead of militarily. After all wasn’t it John F. Kennedy, a Democrat, who allowed the Central Intelligence Agency to invade Cuba in the first place? Since the Bay of Pigs debacle we have maintained frozen relations and hostile criticisms. If we truly wish to be good neighbors, maybe we ought to stop trying to start a coup d’état every time we disagree with the elected regime.

The Obama administration has a lot on its plate right now, especially with their failure in the Iranian negotiations. Playing hardball all the time is a great way to ensure your reputation as a prick and until diplomacy has been exhausted we ought to keep our force projection in check. Sanctions of mass destruction cannot be tolerated if we wish to be a symbol of strength to our neighbors.

If you’re inclined to be less optimistic of diplomacy, that’s alright. It very well could end up that despite all of Castro’s talk of Mr. Obama being the first honest American president, he might consider Mr. Putin a better ally. If this is the case, then I would urge you to consider the political strategy that one ought to keep their friends close, and their enemies closer.

Cuba is the hottest girl at the Prom right now, and Congress ought to wingman Obama as he tries to make a few moves.