The 30-year-old Lester is eligible for free agency at the end of the season if no agreement is reached with Boston before then.
Though 29 other teams could have a crack at the proven veteran, Lester reiterated that it is, without question, his preference to stay with the only professional franchise he's ever known.
"Like I said from Day 1, I'm worried about right now pitching for the Red Sox, and whatever happens, happens," said Lester. "We're optimistic on everything. Hopefully I come back a couple of more times to [the All-Star Game] wearing the same jersey. That's the ultimate goal. All of that nostalgic stuff -- this could be last time with that, the last time pitching at Fenway -- that's a bridge I guess you'll cross when and if you end up holding a different jersey in front of you."
Though there have been media reports that have suggested Lester is done talking to the Red Sox until free agency, the pitcher himself isn't ruling anything out.
"I mean, yeah, I think everybody is hopeful on everything," said Lester. "Like I keep saying, the right time will come when we can sit down and talk about it -- whether it's tomorrow or whether it's in four months. Like I keep reiterating to [general manager] Ben [Cherington] and to ownership and to you guys, this is where I want to be."
Some potential free agents like to take a hard-line stance when they close in on free agency, warning the current team that they need to strike while there is no other competition.
Lester, however, continues to come across as the epitome of patience, understanding the business of the game.
"Let's say the year ends tomorrow and I go to free agency," said Lester. "It doesn't mean I don't want to be a Red Sox. That doesn't change anything. Now they just have more competition."
With Lester just four months away from being able to test his services on the open market, he could at least be tempted to see what other teams view his value as.
"You can look at it that way," said Lester. "I mean, yeah, whatever. I look at it as, 'This is where I want to be.' When it comes down to it, the first day I hope Boston is the first team that calls me and I don't have to worry about it, if that answers your question."
The only thing Lester has felt uncomfortable with throughout his process of contract limbo is when his teammates have to answer questions about it.
"The last thing we need in last place is to have a distraction," said Lester. "I don't want Jackie Bradley Jr. to have to answer questions about my contract. That's just the last thing I need and that we need right now."
Felix Hernandez will start the 85th All-Star Game for the American League on Tuesday at 8 p.m. ET on FOX, with Lester ready and willing to provide an inning or two out of the bullpen if needed.
"Whatever. I'm just here to have a good time," said Lester. "If it's a batter, if it's an inning, if it's not an inning, whatever. I'm just here to have a good time and enjoy all this and soak it all in."
Though the season has been a disappointment for Lester and the Red Sox thus far, he seemed to be in a relaxed mood during All-Star festivities.
After Sunday's win in Houston, Lester flew to Minneapolis with manager John Farrell, the coaching staff and closer Koji Uehara.
"I think every time you do this it's a little different," said Lester. "Each experience has different things you remember. Now I have two kids that are here being a part of it and one on the way. So it's a little bit different part of my life. Obviously, it's a big honor to be here and wear a Red Sox uniform."