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…


Buy Tamar’s book How to Woo a Jew on Amazon now!

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.

Conversation Starter

by Tamar Caspi under Relationships

Dear Tamar,

Can you please help me to find a way to start a conversation with a woman? Can you please tell me what subjects I should, or should not, talk about at the first meeting? Thanks in advance!

Dear Conversation Starter,

Great question! There are some cute ‘n catchy lines you can use to start a conversation. These include,  “I didn’t know they made Jews like you!” or you can just go the straight forward route with,  “Hi, my name is Tamar it’s nice to meet you.” To be perfectly honest, if a girl is interested it doesn’t matter what you say!

As for conversation topics to avoid, don’t discuss any baggage. Baggage includes past relationships, dramas, illnesses and other types of negativity-inducing subjects. Instead, concentrate on discussing positive topics like the things you have in common — your hobbies, favorite foods, pets, etc. And if you find the conversation could keep going all night, then parlay that into a second date!

What NOT to Say

by Tamar Caspi under Date Night,JDate,Relationships

Julie* recently went on a JDate with Brian, a good looking lawyer who recently moved to town. Unfortunately, the report was not good. Yes, Brian was handsome and smart, but no, he’s not an avid conversationalist. This guy didn’t know the meaning of biting his tongue or having restraint — he was an open book but Julie had barely read the back cover. The more he told Julie about himself, the less interested she became.

Brian proceeded to tell Julie all about his entire life over the course of one drink and one hour: his father’s six ex-wives; the medicines Brian takes for OCD and ADHD; his dyslexia; his skin rashes; his likes and dislikes; and finally – the kicker – his ex-girlfriend. None of the items are particularly funny when heard separately, but when taken altogether it was a dark comedy that had come to life.

Maybe Brian was trying to put all his cards on the table and let Julie know exactly what she’s getting into, but his technique needs some major help. Of the above list, the only topic that should be discussed during a first date is your likes and dislikes. JDate makes you feel like you know someone better than you really do before you even meet, but remember that the person sitting across from you is still a stranger. The prescriptions in your medicine cabinet are not something you would discuss with the person sitting next to you in the doctor’s waiting room, so why share it with a girl you’re trying to impress?

One of the reasons I suggest meeting your JDate matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. You have the topics right in front of you when you look at their profiles, so use it to your advantage and keep to the typical first date conversation topics within those guidelines: why did you choose to go to [college]? Where did you grow up? How did you get started in your career? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business right now. On the first few dates, regale your date with funny, positive and interesting stories about yourself and leave the deeper, sad and bewildering stories for later on in the relationship. Hopefully you will be charming enough with the former to leave plenty of time for the latter.

*all names have been changed

Ready to Give Up

by Tamar Caspi under Date Night,JDate,Relationships,Single Life

Dear Tamar,

I am so incredibly puzzled. I have gone on numerous dates that all seem really great. They’d last an average of 2-3 hours for dinner. My photos are completely accurate and updated.  In fact, I am often thanked for being so honest. I am 48 and look much younger (and awkward to say about myself, but I am considered very attractive). I have teens and am dating men around the same age as me. I have been completely puzzled because I am not being called for second dates by those I would like to have a second date with. One recently texted 30 minutes after the date to say he had a great time…and then no follow up. I am really confused and feel like shelving dating.

Dear Ready to Give Up,

Don’t shelf dating just yet. I look at this from a “so far, so good” perspective: you obviously have good photos (and look like them!), you have a lot of life left to live and the men are spending a pretty big chunk of their time with you. If you remember dating the first time around, you’ll recall it wasn’t easy then either. And now you’re bringing age, experience, kids, and all the pluses and minuses that come with that to the table — and probably so are the men you’re dating. So what’s the problem? Why aren’t you getting 2nd dates?

I think what you have to look at are the conversations you’re having on the dates: are you talking about yourself and asking questions about your date? Or, are you commiserating about your past relationships, the stress of having teenagers and so forth? Although these topics may seem like bonding conversations and you may think that by putting all your cards on the table the man will know what he’s getting into, these topics also have negative connotations and may not leave a man thinking he’s had a great time.  Instead, he may think he’s left a therapy session.

Once you meet someone you like you’ll each have plenty of time to discuss your past, but right now you should be talking about upbeat, positive subjects. What interests and hobbies do you have in common? Play Jewish Geography (but don’t talk badly about anyone, that’s bad karma). Talk about what you’re both looking for in the future. I believe if you stick to these topics on 1st dates you will start landing some 2nd dates. Just don’t give up, it will happen! Good luck!