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Dating Etiquette - Expert Advice


Are old-school manners still the way to go? Our modern love advisors answer questions from both sexes about who pays, when to call, how soon is too soon to date and more.


hat are the dos and don’ts for a first date? Is pulling a woman’s chair out too corny or just right? Dating etiquette can be confusing! That’s why we hosted a chat with Phineas Mollod and Jason Tesauro, authors of The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers. Here, they share their wit, wisdom and on-target advice for all your dating etiquette dilemmas…

Q: Where is a great place to have a first date?
Phineas: A very good option is what I call the frozen concentrate of first dates: the lunch date. The whole thing lasts less than an hour and everything is more relaxed. You don’t have to worry about clothes because you're wearing work clothes, and
“If you are dating somebody on the rebound, it’s your responsibility to watch out for the emotional vampire…”
all you have to worry about is chit-chat. There’s no “Let's go back to my place.”
Jason: It's short enough that you only have to endure misery for 55 minutes, but long enough to make an impression and create a sense of longing for more.

Q: What are the things to avoid on a first date?
Jason: Droning on about work. If you come away from a date not knowing what a person does, I think that’s a good sign. You’ve managed to talk about personal issues. Don’t talk about yourself. You have less of a chance of putting your foot in your mouth. Let them talk.
Phineas: If you have a strong personality, keep it slightly in check on the first date lest you scare off the delicate flower across the table.

Q: What’s a nice way to tell a guy that nothing is going to come of a relationship?
Jason: As a writer, I can tell you that getting a rejection letter is better than getting nothing at all. So give a little feedback, even if it’s only by email: “I don't think this is headed in the direction I’d like to go, but thanks.” You don’t want to burn any bridges — you might need him to hire you at his Fortune 500 company later.

Q: Is it appropriate to make a short thank-you phone call the day after a date, or does it come off as clingy?
Phineas: This is one of the classic etiquette things that never go out of style — the day-after, thank-you call. Even if you get voicemail, it’s almost preferable. It shows interest and need not be anything more than that. It doesn’t have to be “Thank you, you rescued me from my life of loneliness.” Merely, “Thank you, I had a lovely time,” and create a springboard for future plans with “maybe we should do this again sometime.”

Q: Is it necessary to pull out a woman’s chair at dinner, or is that old school?
Phineas: Again, that’s another classic etiquette move which is never amiss. But if it really doesn’t fit your personality, I wouldn’t force it into your repertoire. To push someone’s chair in is nice, too, and while you do it you can lean down and whisper something sweet in her ear.
Jason: Like black or brown shoes in your closet, there are certain old-school manners that must be part of your wardrobe. Learn them; they were good enough for Grandma.

“Like black shoes in your closet, there are certain old-school manners that must be part of your wardrobe.”
Q: Should a lady offer to pay for a meal when she is asked to dinner?
Jason: When someone asks you to dinner, especially in the early going, they’ve identified themselves as the host. And as the host, they take care of things like picking up the tab. To offer is a lovely gesture, but you’re the guest, so be the guest.

Q: I’ve been separated about two months, and I was wondering if it is too soon to have strong feelings for someone else? I want to make sure that it’s not a rebound relationship.
Jason: I think it’s important to issue a warning statement to prospective mates letting them know where you're coming from. Before jumping in, they need to know you're bringing a couple extra bags on this trip. Is it too soon? If you're having strong feelings, act on them.
Phineas: As we say in our book The Modern Lover, if you are dating somebody on the rebound, it's your responsibility to watch out for the emotional vampire, drained by the breakup and hunting for a fresh transfusion to restore ruddy cheeks. If you're the vulnerable one, you should do what feels right within reason; it’s the person you’re dating who should watch out for being the one to recharge your batteries.

Q: When should a person make a move on a date?
Jason: Not in the apartment vestibule at the last minute, as the clock is running down. It’s not one move; it’s a series of building moves throughout the night. It’s a touch of the hand that leads to a stroke of the arm that leads to canoodling in the booth; Eskimo kisses that lead to a glorious make-out session in the parking lot. Phineas says it best: If someone has sat through two and a half hours of dinner with you, are they really going to be against a brush of your lips against their cheek? Be bold. But remember, kissing is with the lips, not the tongue or the pelvis!

Q: How many email messages before suggesting a meeting?
Phineas: I would say four. The first one is your initial strike, your second is the “My, you’re quite interesting,” the third is “Wow, you’re
“Every veteran dater carries some lost loves. After the initial wound heals, it’s a source of wisdom.”
into abstract art, too,” and the fourth is when you say “Let’s take this off the impersonal world of computer screens and see what we look like under the sunlight.”
Jason: You don’t want to get too comfortable with email because anyone can be witty when they have a half day to construct a paragraph. So you want to switch gears and get some face time.

Q: What’s a good way to start a conversation?
Phineas: If you’re at a party, there’s no need to fumble with an opener — you’ve both been invited so you can always just say, “So how do you know [Bob, the host]?”
Jason: I’m a fan of addressing strangers with personalized openers that show you’re paying attention — calling out great shoes or noticing that you’ve read the book they’re reading on the subway, Atlas Shrugged or the most recent Harry Potter book.

Q: What are the best and safest first date topics?
Phineas: The safest topics are hobbies, what you do after work. Sports, fitness, travel, what book you’re reading, what your apartment is like, how many miles per gallon your car gets, dogs, cats.
Jason: Those are all safe, I agree. But if you want to move a date so it doesn’t feel like a job interview, I think you have to interject some provocative topics. You don’t want a wishy-washy mate.

Q: What encouragement can you give to those of us who have been burned and are tentative about getting back out into the dating world, putting our hearts back out there once again?
Jason: It hurts so good, though, doesn’t it? I’m a glutton for that kind of pain and suffering. That's part of the human condition — wearing your heart on your sleeve and having someone use it for a piñata now and then. You can’t get hard-hearted about it.
Phineas: I would just say join the club — know that every veteran dater is carrying some lost loves that poke into his or her head daily, weekly or once in a while. After the initial wound heals, it’s a source of wisdom that you take to your next love.
Jason: Broken bones heal stronger; broken hearts, too.


Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train and keeping up the newlywed vibe after passing the underrated 1.5-year mark with his wife. Jason Tesauro toils at a vineyard by day and writes at night while he and his wife scratch their seven-year itches... together. Together they are authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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