Second Date Series: How Do You Like Me Now?

by Tamar Caspi under Date Night,Relationships,Single Life

While you’re on a second date, your conversation should start getting deeper and deeper (as well as on your third and fourth dates). This is not just superficial conversation; you should be asking questions and discussing more in-depth topics. To find out if you enjoy the same topics, you can mention them and see what reaction you get: A blank stare? An eye-roll? A passionate debate?

If you like world events, mention the Iran Deal, Greek’s economic collapse, or ISIS. If you enjoy science, then mention global warning or stem cells. If you love entertainment, then bring up the recent Emmy nominations, Amy Schumer, and anything else trending. If you’re passionate about politics, then broach the topic of Donald Trump and then the dozen other Republican candidates. If current events get you going, then bring up the topic of racism and if police are using unnecessary force. And of course, there’s sports… but that’s an easy one.

You may find that you cannot see yourself with someone who doesn’t read the newspaper, or someone who only gets their updates from TMZ, or someone who’s politics differ too much to understand, or whose schedule revolves around SportsCenter. Differences are good, but you need to have respect at the core in order to have a healthy debate. If you do decide to enter into a debate during a date — which is fine — be respectful and don’t hurl personal insults or allow it to upset you. If that happens, then you likely have your answer about the fate of the date. Remember that looks fade, but the ability to have enticing conversation can last forever.


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First Date Tips: Conversation Starters

by Tamar Caspi under Date Night,Online Dating,Single Life

After playing the JDate game (viewing, favorite-ing, messaging, etc), exchanging a few emails and a couple quick phone calls (to make and confirm plans), you will no doubt find yourself battling nerves before a first date no matter how confident of a person you are. Once you’ve greeted each other, sat down at the bar or table, ordered drinks and discussed the menu, there is a time when the conversation may lull — and it’s nerve-wracking!

Don’t let that moment set the tone for the date. Be prepared with topics to bring up that will be a catalyst for ongoing conversation. Of course there will be the typical biographical questions (what you do for a living, your hobbies, where you grew up, your family, etc.) but most of that was likely covered in your initial emails and phone calls, and now you need to see if you can actually carry a conversation and jive with the other person.

Think of some thought-provoking questions like:

  • What do you hope your life looks like in 5/10/20 years?
  • Are you where you wanted to be in life 5/10/20 years ago?
  • If you could have a superpower what would it be and why?
  • What is your best memory from your childhood?
  • Who are 5 people, alive or dead, that you would love to talk to?

The key is to not make it sound like a rehearsed question or an interview, but rather work it in somehow… “Hey that Caitlyn Jenner interview has really made me think…” or “My 96-year-old Great Uncle just passed away and I’ve been doing some soul searching…” and so on. Current events are a great tool: “Remember that Malaysia Air plane that disappeared in the ocean? It really got me wondering about the supernatural. Do you believe in…?”

Finally, listen to your date’s answer rather than being ready to pounce with your answer or another question. A lot of conversation will likely naturally occur, but if you are mentally preparing for what you’re going to say next then you will miss out. If you are a shy person then ask a friend or relative to practice with you.

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Email Etiquette — How Do I Start a Conversation?

by Tamar Caspi under JDate,Online Dating,Single Life

Hi Tamar,

I have no idea how to start a conversation with someone I’m interested in. What should I say that’s not too much… but just enough.

Thank you,

Lost in Conversation


Hi Lost in Conversation,

Great question! Interestingly, when both people are already intrigued by the other’s profile, it really doesn’t matter how you start the email as long as you take the time to send one. That said, here is an example that you can play around with and personalize:

Hi there,

I was attracted to your profile by your photos, but I was really impressed by what you wrote, especially _____________. We have a lot in common (which you can see by reading my profile) and I’m always excited to meet people who also love ________________. Have you ever ________________?

Looking forward to hearing from you,


Leading with Looks

by Haley Plotnik under Online Dating,Relationships,Single Life

I get far too many messages about the way I look. The same way that getting a “Hey, what’s up?” message can be frustrating in that the conversation fire hasn’t been lit, it’s hard to continue a conversation when someone messages, “You are so pretty!” Once you acknowledge the compliment (or not), you still have to make a fast u-turn to get into good conversational territory.

Let’s look at some ways to respond to a looks-based message:

1) The good old fashioned thank you

Initial message: “You are gorgeous, wow!”

Response: “Thank you very much!”

Where did that really get you? Maybe you brightened up the recipient’s day, but now you have to start a conversation from scratch.

2) The thank you/ u-turn

Initial message: “You look like a real life Disney princess!”

Response: “Thanks. I love Disney movies. My favorite is _______. How about you?”

At least the compliment helped a little in this instance. Sometimes it’s more like this:

“You’re cute. I’m _________. I look forward to hearing back.”

“Hey, thanks! What do you like to do for fun, _________?

3) The bratty response

Initial message: “You are stunning. I would love to get coffee.”

Response: “Yeah. You and every other Jew in New York.”


Not only do I have trouble responding to these looks-based messages, but I also feel like my better personal qualities aren’t being valued. For me, one-line, looks-based messages don’t stand out among the pack. I don’t typically reply, even if I am interested in the guy, because I am looking for someone who appreciates more than being easy on the eyes.

Next time, try a messaging someone with NO looks-based compliments. See where it gets you. Here’s a start:

“Hey. I noticed you like _________. I’ve wanted to try _________ and was wondering how you got into it…”

This is not the most creative. Some people are super creative and comic. If that’s not your thing, don’t try to be something you’re not. Be yourself, but don’t be obsequious. Leading with looks makes me wary that the sender may be a panting puppy when it comes to approaching a potential date. Coming on strong is called coming on strong for a reason. It’s too strong for many people. If you come on too strong, someone may be offended. I’ve yet to be offended by someone not hitting on me enough. Maybe you’re not exactly mysterious or aloof. I’m not either, but it’s typically better to tread lightly. Once you’re in back-pedaling territory, you’ve likely lost the battle.

What Do You Do?

by Aaron under Single Life

We’ve all been there. You meet someone new, you get a name, and you think to yourself “what would get a conversation rolling?” It probably occurs to you that people like talking about themselves, and what could people love more than their job? So you ask it: “What do you do for a living?”

I’ll let you in on a secret. Some people like that question, but a lot of people see it for the conversational crutch it really is. Asking “what do you do?” is a faux pas in a few ways. For starters, you’re assuming all people like their job, and sadly that is not the case. I know when I was working retail I told very funny stories about things that happened to me (like a river of urine I found in my store), but it was the last thing I wanted to associate with new friends. Secondly, some people may take it as you trying to gauge how much money they make. And lastly, sometimes people just want work to stay at work.

When this question comes up, some friends and I have vowed not to reveal our jobs within thirty minutes of first meeting someone. We’ll say ridiculous jobs like bounty hunter, fruit bowl modeler, or selfie coach, and move the conversation along. So in order to help others make a more fun, lasting connection with a new friend, here are my three alternative suggestions for that rut when you need something to say:

  1. Talk about what’s around you. One of my favorite social rules is called “Observe, Share, Ask.” You see something in a room, mention something about it and how you relate, and ask something about the other person’s experience. For example, if I was in a room and saw a picture of a clown, I would say something along the lines of “did you see that clown picture? The circus always terrified me, did you ever like it?” This allows me to share a bit about me while sharing an experience (we both see the picture), and allows the other person to open up about their experiences.
  2. Ask how they got there. Whether you’re at a party, synagogue, or a singles mixer, ask someone who they know or how they found the place. This allows you to find mutual friends (this was my usual conversation starter at parties in college), and build a connection about any hooks that are revealed — they could be classmates, fellow natives, or mutual friends.
  3. Ask what they do in a different way. This is a fun one to me in that you still get to ask the job question — if they want to talk about it. An article I found on LinkedIn a while back had the amazing option of asking “What keeps you busy?” This is such an amusingly vague and open question that people can answer with anything from, “I blog for JDate and collect beer glasses” to what they do for a living.

Hopefully this sparks your conversations a bit, feel free to leave other ideas in the comments!

Speed Dating? Read This!

by Tamar Caspi under Date Night,Single Life

After hosting a HurryDate event last week, I have some advice that all singles who are planning to attend speed dating events should read:

1. Dress to Impress

There was a man there wearing a hat. Really? Just like your JDate profile photo, why on earth would you show up wearing a hat? There were ladies wearing sandals. Not only is it February, but there is nothing sexy about sandals.

2. Be on Time

It’s tough to start the event if all the people aren’t there. Check in and then go grab a drink from the bar.

3. Smile

Nothing says “approachable” better than a smile. That, and don’t cross your arms over your chest.

4. Be Conversation Ready

Most of the questions that can be asked within the five-minute time frame of the speed date are the obvious ones, so be prepared to answer: “What do you do?” and “Where do you live/Where are you from?” And try to answer with easy, one-line answers that you haven’t rehearsed.

5. Don’t Ask: “Why Are You Still Single?”

“Why are you still single?” and “What is your relationship history?” are questions to be saved for a later time. If someone asks you these questions during a speed dating party, then your answers should go like this, respectively: “For the same reason you’re still single, I haven’t met the right person yet” and “I’ve been in some meaningful relationships where I’ve learned a lot about myself and what I want in a mate, and I’d be happy to share that with you on another date.” Then change the topic.


Finally, stick around after and socialize. You may meet another single to attend future single events with you, or you may get to continue talking with someone, like the couple who was still chatting an hour after the event ended last week…


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Make a Move

by Tamar Caspi under Single Life

So many people let love pass them by because they simply are afraid to take a risk and say something. Whether it be “What’s your friend’s number?” or “Are you single?” or “Would you be willing to set me up with your buddy?” or “Would you like to go out sometime?” or simply saying, “Hi! My name is…”

That’s all it takes to see if that girl you saw volunteering at the JDate event is available, or if that guy you saw hanging out by the kitchen at your friend’s party is Jewish. What’s the worst that will happen? You’ll find out the person is either not Jewish, not single, or not interested. No big deal, right?! Make sure you don’t regret not saying something.

Playing Hard to Get on a JDate

by Tamar Caspi under Relationships

You give off so much information in your JDate profile that by the time you exchange a few emails, have a phone call and make plans for the first date, you already may get the feeling that you know your prospect much better than you actually do. So when the first date rolls around you end up sharing much more than you normally would because there is an automatic comfort level with knowing how old someone is, what general field they are in, where they’re from, what they’re looking for, and so on. And if you’ve done any cyber-stalking — admit it, you at least tried! — then you may know even more.

After the date ends, whether good or bad, you’re left feeling like you may have overshared. It’s easy to overshare on a first date, especially when it’s going well. Try, try, try to reign it in, you’ll be happy you did if the date sucked and you’ll be happy you did if the date went well. Even when a first date lasts for hours upon hours until you end up watching the sunrise together because you can’t stop talking, there are many tidbits of information NOT to share. This is not about playing a game as the title of this post alludes to, but rather playing hard to get by keeping everything in perspective.

Yes you know a lot of information from someone’s JDate profile, but you don’t know them. Your JDates are still strangers, treat them as such until you know there is even somewhat of an inkling of a future. Your relationship past is not fodder for a first date, neither is your family drama or your finances. Keep the first date chatting to expanding upon some of the questions asked in your profiles: where did you grow up and how did you get to (or get back to) your current town? where did you go to college, what did you study and why? what do you do for a living and is this your passion or what do you really want to do with your life? Allow those questions to lead to further conversation, but without getting too deep too quickly.

A Distant Memory

by Tamar Caspi under Relationships

You spent two hours reading his or her profile, exchanging emails and having a few quick phone calls as you made plans. Then you spent an hour getting ready, a half an hour getting to the restaurant, and three hours on the date. Then why, six and a half hours later, can you not remember anything about the date? Sure, you can remember the food and you recall that your date was a blonde (or brunette, or short or tall, etc) but there is nothing special about your date that sticks in your mind. Did you not ask enough questions? Did you not lead the conversation somewhere interesting? What attracted you to this person in the first place and why did you not capitalize on that? If you did try all of the above and still the date went nowhere then it was just a dud date and you need to move on. But if you just sat there and hoped your date would do all the work then you need to wake up and make more of an effort if you don’t want to be single forever.

Email Mystery

by Tamar Caspi under JDate,Online Dating,Relationships

One of my single friends forwarded me the funniest email she received from a JDate. It said (identifying details have been removed): “Hi, my name is xxxxx. I live in xxxx and am a lawyer. In my free time I like to watch and play sports. I just signed up for JDate last week.” Yup, that was it. It was all about him but nothing new that she couldn’t have learned from looking at his profile. There was nothing about her and why he wanted to start up a conversation with her and there were no questions for her to answer to create a tete a tete. So what was his point in writing her?  Why bother? I’ll give him some benefit of the doubt since he’s new to JDate, but if you’re going to write an email make it worth it. Tell your prospect WHY you choose him or her to write to and ASK more about him or her.