Here Are Some Things to Do on a Date … and Not to Do

Two O.C. experts weigh in on the rules of first dates.
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Photo by Josh Felise on Unsplash

From figuring out what to talk about on a date to dealing with how to tell someone you’re just not interested, navigating the dating world can feel overwhelming. We spoke with experts Kathleen Cover and Julia Bendis to get the answers. Read on to learn how you can land a second date.

What advice would you give to someone who’s going on a first date?
KC: Be well versed in social and fine dining etiquette. When we know what is expected of us, we naturally relax and can focus on every moment of the date. If you bring your good manners and charming personality on the date, many more may follow.

JB: I know people get nervous, but you can’t treat it as an interview. You have to go into it thinking, “I’m just talking to a friend, I’m just getting to know someone.” A lot of times people make the mistake of sitting down and chit chatting about unimportant things and realize they don’t know anything about that person because they didn’t ask the right questions.

What are the right questions?
JB: Talk about their family, where they’re from, what they’re passionate about, what they want in a partner, what’s important to them in life, where they’ve traveled, what books they’re reading.

What about past relationships?
JB: Of course you can say, “I’ve been married before,” or “I was in a long term relationship.” But you don’t need to go into detail and say why it ended or bash your ex.

Anything else you should avoid?
KC: The three biggest missteps are talking too much about (yourself), not being aware of how (you’re) negatively being perceived when interacting or speaking with service staff, and using or even looking at any mobile device—all focus should be on your date unless it’s an emergency. Be cautious about talking about sensitive topics such as past relationships, politics, religion, personal finances, and general gossip. Be prepared to keep the conversation going by sharing pleasant happenings in the news that day. And always be prepared to graciously maneuver an unpleasant topic back to the appropriate track.

JB: Don’t talk about politics or controversial topics. Do not talk about yourself. No woman gets turned on by your Porsche or how much money you make. Don’t brag—eventually, she’ll find out you won an Oscar.

Should you drink on a first date?
KC: Be cautious about alcohol consumption. Tip: Sparkling water in a stemmed glass is a nice alternative when others are enjoying alcoholic beverages.

JB: People get very comfortable when they’re drinking and start saying things that are completely inappropriate on a first date, like inappropriate jokes or they start going into detail about sexual things. I ask, “Why did you talk about that?” and they say, “Oh we were just talking and it just happened.” No, it doesn’t just happen; you need to keep your mouth shut!

Who should pay on a first date?
KC: Whoever initiates the invite is expected to pay. It is perfectly acceptable and kind to offer that the expenses be shared, but don’t insist on paying if the person that initiated the date wants to pay for all expenses. If it’s a dinner date and your date is picking up the check, be aware of the cost of items you are ordering no matter how financially established your date may be. If the date is going well and continues on, it is acceptable for the “guest” date to pick up after-dinner (expenses).

JB: If you’re a gentleman in a heterosexual relationship, you should pay. I know it sounds old fashioned, but that’s just the way it is. I mean how much could it be on a first date? It’s glass of wine and an appetizer. If he can’t afford it, he shouldn’t be dating!

If a date is going poorly how can you get out of it?
KC: Remain gracious and continue to engage in conversation even if you realize quickly there won’t be another date. Unless your date is being disrespectful, you may want to try to stay for an appropriate amount of time.

JB: Don’t do long dinner dates. Meet for a glass of wine or appetizers. If it’s going bad, be polite. Just leave some money on the table and say, “Thank you so much, it was great meeting you, but I’m going to go ahead and go.” And there’s no shame in saying that. If he’s being so inappropriate you just can’t stand it, end it on a good note—you don’t want to anger someone especially if you’re meeting online and you don’t know that person. And you can always ask the server, manager, or bartender for help.

How do you tell someone you’re not interested in a second date?
KC: Keep it honest, respectful and considerate—everyone deserves a courteous explanation and goodbye. Let them know how much you enjoyed meeting them, that they are a nice person, but that you just did not feel a connection between the two of you.

JB: Do not say yes to a second date if you’re not feeling it. It’s a lot harder to go back and say no. Just say, “It was great to get to know you, but I’m just not sure if there’s a connection.”

If someone is ghosting you after a first date, what should you do?
JB: There’s nothing you can do. If he completely just falls off the earth, blocks you on social media, doesn’t respond, then you’re done. You don’t want somebody who will completely disappear. If he can’t do that simple gesture of a five-minute phone call to explain himself, then you don’t want him.

How do you ask someone out in public without seeming creepy?
JB: Don’t start with a pick up line. Depending on the situation, if she’s working out, most women will want to be left alone. Don’t go up to her while she’s sweating on a treadmill. If you keep seeing the same person at the gym, wait till she’s done and just say, “Hey I’ve seen you here and I just want to introduce myself.” Make it casual and treat her like a friend. Women should approach men too; it goes both ways!


Julia Bendis is founder, matchmaker, and coach at Match By Julia, matchbyjulia.com

Kathleen Cover is founder and president of The Etiquette School of Beverly Hills and Newport Beach, pelicanhill.com/etiquette

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