Go ahead and try pinning down Montgomery County Executive Isiah "Ike" Leggett about whom he'll endorse in the Democratic primary for governor. Leggett may smile politely, but he will be wincing on the inside.
You might as well ask him which of his family members he prefers most. Can you say "awkward"?
Leggett's dilemma: Two of the principal contenders, Attorney General Douglas F. Gansler and Del. Heather R. Mizeur, are from his county, and he knows Lt. Gov. Anthony G. Brown well.
Party leaders such as Leggett, whose endorsement is coveted because he oversees Maryland's most-populous county, are often skittish about selecting a candidate in a primary. The risk — alienating a current or potential ally — can outweigh the benefits.
"I've always hated primaries and try to stay out of them," said former Democratic Rep. Michael D. Barnes. "It's more fun to be engaged in the general election."
Still, Barnes has endorsed Gansler. "Doug has been a friend for decades. I think he'd be a very strong governor," Barnes said.
Leggett himself is in a primary battle with two competitive opponents.
"For Leggett, it makes no sense for him to endorse," said former state Sen. Barbara Hoffman, a Baltimore Democrat. "It doesn't help him if he wants to be carried on everybody's ticket.
"You can ask him," said Hoffman, now a consultant and lobbyist. "But I don't think he's going to tell you anything."
In fact, this is what Leggett said when asked last week when he will choose his candidate: "June 25th is looking good."
The primary is June 24.
Leggett was joking about the date, but he said he genuinely isn't certain who he will back, if anyone.
The endorsement dance can also be sensitive for the candidates doing the courting.
Consider Gansler, who met with Maryland House Speaker Michael E. Busch last year to try to win the Anne Arundel Democrat's backing.
The odds weren't in Gansler's favor. Brown had served on the House Economic Matters Committee when Busch chaired the panel, and the two got along well.
"Doug and I had a discussion," Busch said last week. "He said, 'I know the relationship you have with Anthony.' I said, 'Doug, it's not a personal thing. I just believe strongly in Anthony Brown.'"
Busch announced in October that he was endorsing Brown.
Experts say the endorsements that matter most come from well-regarded politicians willing to actually do something for the candidate — for example, aid in voter turnout efforts — rather than just lending their names to the cause.
"Endorsements have a cumulative value," said Del. Samuel I. Rosenberg, who has endorsed Brown. "There are only a handful of people with the stature within the community that their endorsement by itself [is influential]. For everybody else, it's a cumulative assessment."
There are far fewer Republicans than Democrats in the state. The candidates vying for the GOP nomination — Del. Ron George of Annapolis, former Ehrlich administration official Larry Hogan, Charles County business executive Charles Lollar and Harford County Executive David R. Craig — have collected substantially fewer endorsements than the Democratic contenders.
Former Gov. Robert L. Ehrlich Jr., a Republican, attended a rally for Hogan — his former appointments secretary — but has made no endorsement in the race. Ehrlich could not be reached for comment.
While Leggett and others remain neutral, hundreds of elected officials and organizations across the state have endorsed Brown, Gansler or Mizeur.
Brown has captured the biggest names, including former President Bill Clinton, both of Maryland's U.S. senators, most of the state's Democratic U.S. House members, as well as state Senate President Thomas V. Mike Miller.
Gansler, a two-term attorney general and former Montgomery County state's attorney, has labeled himself the contest's "outsider."
"I do know what I'm up against," Gansler said. "It's the status quo."
Those who do endorse are hoping nobody feels snubbed. Or that candidates not receiving endorsements understand it's just politics. Or have short memories.
No matter what he decides, Leggett knows he will have to do some explaining to candidates he does not back. "Out of respect to everybody, you would do that," he said.
It's a delicate process, isn't it?
"Very much so," Leggett said.