Vice President Joe Biden earned the commander in chief's approval when he sank a 15-to-20 foot putt on the first hole, a par five, at Joint Base Andrews.
"Did you all catch that?" Obama shouted to reporters gathered near the green.
The president sent his putt just past the hole before tapping in. Boehner, considered one of Washington's best golfers, gave a hearty "Oh yeah!" after draining a short putt.
Obama, who's not in Boehner's links league, patted the speaker on the back as they headed toward the second hole, the president driving their cart.
Aides say the time that Obama and Boehner are spending on the course could help improve a relationship that's respectful, but hardly close.
But 18 holes probably won't give them enough time to hash out their policy differences on everything from the debt to the U.S. military involvement in Libya.
The outing comes against the backdrop of negotiations between the White House and Congress over a long-term deficit reduction plan that will set the stage for increasing the amount of money the government can borrow.
Republicans have insisted on significant cuts of about $2 trillion over 10 years or 12 years before agreeing to increase the current $14.3 debt ceiling, which the government says it will surpass Aug. 2.
Biden is leading a group of bipartisan lawmakers in deficit talks, and he was Obama's golf partner.
Boehner picked a fellow Ohio Republican, budget-cutting Gov. John Kasich, to join him for the round. Kasich was House Budget Committee chairman in the 1990s when Republicans were negotiating budgets with Democratic President Bill Clinton.
While both sides say they're optimistic about the progress being made in the deficit talks, Boehner has suggested he and the president may need to get more closely involved in order to reach a deal.
The White House has played down any expectations about that happening on the golf course.
"I can say with great confidence that they will not wrap up the 18th hole and come out and say that we have a deal," presidential spokesman Jay Carney said.
Policy tensions between Obama and Boehner also have extended to the U.S. military campaign in Libya.
Boehner led the House in passing a resolution that chastised Obama for failing to provide a "compelling rationale" for U.S. involvement, and has said Obama is in violation of the War Powers Act. In return, the White House has sought to discredit Boehner's position on the act, sending reporters old statements Boehner made questioning the constitutionality of the measure.
Boehner had a clear advantage over Obama on the scorecard.
The speaker reportedly shoots in the low-80s, good enough for the magazine Golf Digest to recently rank him 43rd among 150 prominent Washington golfers. The president, on the other hand, was ranked 108th.
"Boehner's a much better golfer than I am, so I'm expecting him to give me some strokes," Obama said in a recent television interview.
The president is likely to get a boost from Biden - Golf Digest's 29th best golfer in Washington.
White House officials are playing coy about whether they will release the score. The group played the par-72 East Course, one of three 18-hole courses at Andrews.