I remember way back in high school when my best friend skipped a day of school with her boyfriend of the month. It was just around the time we were sending out our letters of recommendation to the schools of our choice -- and my friend was applying to all the top ones.

All the other students thought it was hilarious when she got caught (she was the valedictorian-to-be). But her family didn't: I remember her grandmother saying that she had ruined her life, because no college was going to accept her with that black mark against her name.

Of course, she turned out fine and is now on her way to earning her PhD in an intimidating subject -- cell and molecular biology.

As our friends in the workplace advance beyond their entry-level positions, many of them with episodes a little racier than a day of skipping high school in their backgrounds, the question arises: What do you do if you have a "youthful indiscretion" on your record?

Do you 'fess up in the interview? Do you worry only if you were convicted of a crime? And if it was a conviction from those crazy college days and has nothing to do with your present job, does it even matter?

Employment lawyers contacted for this column all said the same thing: You shouldn't be concerned unless you have a conviction, and even then, it shouldn't affect anything unless it has a direct impact on your job.

We all know about this town's obsession with disclosure. But you shouldn't be passed over for a job just because a background check on you revealed that you used an illegal substance years ago, said Deborah P. Kelly, employment lawyer and partner at Dickstein Shapiro Morin & Oshinsky LLP in Washington. "Take it from the Boomer Generation: If that was it, we'd all be on the streets without a job," Kelly said.

Lies

Some employers ask if an applicant has been convicted of a crime. Take Mom's advice on this one: Don't lie.

Instead, "indicate what happened and when," said Michael D. Karpeles, partner and head of the employment law group at Goldberg, Kohn, Bell, Black, Rosenbloom & Moritz Ltd., in Chicago. If it was a long time ago, the employer should understand, he said.

Use some common sense and remember that employers would rather their hires be honest.

Case in point: A 23-year-old employee at a firm in Northern Virginia recently applied for the job of driving the company's promotional truck. The employer kept asking for the worker's driving record, but he kept delaying. Finally, the day he was supposed to pick up the truck, the company received his driving record -- complete with a DUI conviction.

"We wanted to reposition him in the company because he's a smart guy, but now he's embarrassed and may leave," said an employee in the human resources department who wished to remain anonymous. "Had he been upfront, we may have been a little better about it. This was his first real job and this trust issue was violated."

The employee had thought that if he proved himself to his company and showed what a responsible driver he was, management could later overlook his DUI if it came up.

Bad move.

Chris Jones, president of PoliTemps, a legislative, government and political temporary staffing service in the District, said that coming clean when the company asks job candidates to do so is pretty much imperative.

"It would be in their favor to [tell the company] because they're being honest. If it turns up later, the employer is going to be like, `Why didn't you tell us?'"

And if the company freaks out when you admit to a conviction? Then perhaps the position is simply a bad fit.

The Rap Sheet

Sometimes the skeleton in the closet is something a bit more serious than a wild-oats misdemeanor on a spring break beach. But, said Kelly, a conviction still should not keep you from getting hired unless it directly affects the job you are applying for. That would not include convictions of "moral turpitude which bespeak that you're a yucky type of person."

"If it doesn't relate directly to your job, it shouldn't matter," Kelly said. "I never tell companies to elicit information about arrest records, only convictions, and the conviction has to be related to the job that you will be doing" before the company can toss your application in the can or, worse, fire you.

"Employers have obligations as well and have to be careful when screening out employees with criminal records," said Karpeles. "But it's safest only when the crime relates to the job that they get cut, because it's possible that someone could bring a discrimination claim against the company."

Legally, said Kelly, a company cannot ask you if you've been arrested. So don't tell. "There's lots of things we have done that are just part of being younger and they shouldn't damn us when we become adults," she said.

Did You Inhale?

On the other hand, anything above getting caught with a joint could matter when you're applying for a sensitive position with the government or with a high-profile company, said PoliTemps' Jones. (And sometimes even the joint, if you are applying to, say, the CIA or Secret Service, said Kelly.)

If you aren't asked, it's not necessary to mention a small drug possession or other misdemeanor, Jones said. If it's a bit bigger than that, you probably should volunteer your conviction.

Whereas with most employers a single conviction on your record should not cause a problem unless it can be related to your job, any conviction could be a potential problem if you work for the government.

"If you're working for the government, you owe it to your employer to give them a heads up. The last thing you want is for that to end up in the press," Jones warned.

If you have been convicted of something serious, there are ways to approach the subject with employers that won't immediately eliminate you from the running.

Explain to them, Jones said, that "I had a run-in with the law in my youthful days and I thought you should know about it. I served my time, did my probation." That approach, he said, may even earn you brownie points.

Jones's advice is always to err on the side of honesty in dealings with employers. "They appreciate it because they see you're a straight shooter. If they see that and can't look over that youthful indiscretion, then you don't want to work for them anyway."

If you have questions about getting ahead, you can e-mail Amy Joyce at joycea@washpost.com