Our columnist takes on one of the thornier problems with tipping.

Dear Ms. Etiquette: I went to an awesome new salon the other day and left a huge tip. Do I have to tip that much if I go back?

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I’m a big believer in tipping. Especially when someone’s doing your hair. Especially the first time. I talked to Matthew Collins, who cuts celebrities’ (and normal people’s) hair at Brennen Demelo salon in Toronto, and he agreed: “The first service is harder for the hairdresser and the client. We have to get on the same page with each other. The consultation alone takes at least 15 minutes, and we haven’t even started doing the cutting yet.”

Tipping is always one of the more confusing financial transactions we make. But it’s especially awkward when you’re dealing with a special subset of tip-ees: people with whom you may end up having a kind of personal relationship. Think: a barber, a massage therapist, a caddy, etc. Here’s the way I look at it. The first haircut—or round of golf, or Shiatsu—is like a first date. You’re both a little nervous, hoping it will go well. And if it does, you’re really happy, and unlike on a date, it’s OK to express that happiness with money. OK, so far, so good. But what about that next visit and the possibility that you’ve dug yourself a financial grave with that initial generosity?

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Guess what: You haven’t. In my opinion, the return trip should be a return to a normal tip (say, anywhere between 15% and 20%). It is, in a strange way, a sign of respect. When you show your face again at his salon, or golf course, or Pilates studio, you’re going to make your service provider happy—regular clients are the lifeblood of anyone who lives off of tips. But he won’t be expecting another windfall. He’s just happy to have your business.

From there on out, it’s best to keep it steady—as long as the service level is maintained, the amount of money you tip should also be maintained. If you always hand $80 to your caddy but you had a bad round? Don’t take it out on him. And, hey, even if you asked for advice and he steered you wrong, you can’t blame him for all of your duffs.

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One deeper wrinkle: Eventually, you may become friends with this person. Or at least kind of friends. It’s bound to happen after your conversation evolves past, say, your split ends and veers into a play-by-play of last night’s fight with your boyfriend. You may be tempted to start feeling awkward about it. Should I tip more because we’re pals? Or will this person be offended when I try to give them money? I’ve got three words for you: Get over it. As long as one of you is providing a service and the other is benefiting from that service, a tip is expected and appropriate. It might be weird to you, but it’s not weird to the person receiving the tip. Chances are he gets money from people he’s also friends with multiple times a day.

Now there’s one more thing to talk about: The power of being a big tipper from the first visit to the last.

“If someone leaves a great tip every time, I’m 100% going to remember that,” says Collins. “I have a six-month wait right now, but if there’s an opening, that person is certainly going to know about it.”

Joe Martino of New York City’s Orlo Salon agrees. And he even believes an exchange of goods and services is implied. “I have some clients who tip almost the same amount as their services cost, but something is expected on my end with that kind of luxury,” he explains. “They’re usually the ones who’ll call on the busiest day, saying they need to come in within a few hours. I’ll do everything possible to make that happen. And they expect me to. But, hey, we’re both benefiting.”

Oh, and there’s one more reason to tip more sometimes. Because your dog walker or massage therapist or private yoga instructor deserves it. When the service provider has gone above and beyond the usual call of duty, your tip should also rise above.

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