The second time, he learned he'd have to stop going for drinks with friends who smoked for awhile.
The third time, he found that a quitting strategy that had him increase the time between cigarettes wasn't for him.
"I just kept looking at my watch to see if it was time to smoke again," said Dr. Klingemann, a pharmacist at The Nebraska Medical Center and a tobacco cessation expert. "It was horrible."
Finally, on his sixth attempt, he succeeded.
What he later realized was the relapses taught him lessons needed to kick the habit for good.
Long-term relapses generally occur for two reasons, Dr. Klingemann said, stress and/or over confidence.
Acutely stressful situations, such as deaths, a new child or job troubles, can lead tobacco users back into addiction.
Another common relapse scenario plays out as such: a former user goes some time without tobacco, heads out with friends one night, decides he or she can "just smoke one" only to find he or she cannot.
Short-term relapse is more common as users are overwhelmed with triggers -- behaviors or actions that spark the urge to use tobacco -- and the physical withdrawal of nicotine addiction.
Dr. Klingemann urges his patients to plan ahead and account for triggers and urges. He has them learn their patterns of tobacco use and ways to change them.
"Tobacco addiction is a subtle enemy that is often underestimated," Dr. Klingemann said. "If you plan to confront the various pitfalls, you may not have to go through the struggles many of us did to quit."