Dear Tamar: Compliments Make Me Feel Awkward

by Tamar Caspi under Date Night,Online Dating

Dear Tamar,

I’ve always had a difficult time accepting compliments but obviously I’m put in the position to hear them on first dates (not trying to be egotistical, people just tend to offer a lot of flattery when they first meet). So I guess what I’m asking for are a few pointers of how to say thank you while making it sound genuine without sounding like I expect the compliment either.

-Attention Non-Seeker ______________________________________________________________________________________________

Dear Attention Non-Seeker,

You’re right, flattery is part of the dating game. Obviously we go on dates with people we find attractive and want to let those people know so. Replying is tricky, you’re correct there as well. Here are a few responses to have in your arsenal:

  • “Thank you, that’s very sweet, I appreciate it.”
  • “Awww, really, you think so? Thank you!”
  • “Thanks, no one ever compliments me on that, how kind/cool/sweet of you to notice.”
  • “Thank you! You know, I was just noticing how amazing your eyes/smile/skin is!”

But it’s not just the words, you have to match it with your tone and facial expression. Work on making sure your voice sounds genuine when you say it by smiling — but don’t fake smile, a real smile means your eyes will smile too (“smize” if you will, a la Tyra Banks) and that will help support the authenticity of your reception of the compliment.

Get more advice by following @howtowooajew on Instagram!

Dear Tamar: How Long is Too Long to Wait for a Reply?

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

Dear Tamar,

I went on two pretty good dates with a guy from JDate last week, and sent him a text wishing him a Happy Sukkot and a good week on Monday. Now it’s Tuesday and I haven’t heard back.

What do I do?



Dear Waiting,

Well… I have two responses you probably don’t want to hear.

The first, is that you shouldn’t have texted to begin with, even though you had really sweet intent. But, we can’t go back and undo the past. It’s too early to be communicating via text since you don’t know each other well enough. Stick to short phone calls that are primarily for making plans. Only after at least half a dozen dates consistently for a few weeks should you begin texting. Exceptions are to let your date know you arrived home safely and thanking them again for a nice evening.

The second, is that if he hasn’t texted you back by now, then chances are you may not ever hear from him again. Is it anything you did? No. Was it the text? No. This guy just wasn’t as into you as you were into him. It sucks. There is a chance that he saw it, couldn’t reply at that exact moment, and then forgot. But, the hope is that a guy who likes you will have thought about you at some point since then and recalled that you sent him a text. Waiting a full day if not longer to reply is not playing hard to get; it’s just being a jerk. Move on.

Now, is there a chance that he could call this week and ask you out again? Sure. It is a bit egocentric of us to believe that people’s lives should revolve around replying to texts with someone we’ve met twice, but then again if you like someone then you would reply in an acceptable amount of time. If you’re playing hard to get then maybe you wait an hour… but a day? No. We are on some sort of electronic device far too often to have any other excuse aside from the person simply not being a priority.

Alas, it’s been two dates and one day since the text so all is not lost. If you choose to accept the date, then don’t even mention the text — the last thing a new dater wants is someone who overreacts to such things.

Follow Tamar on Instagram for more dating tips @howtowooajew


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

A few weeks ago I answered a JDater’s email about ghosting, and now it’s a topic of an article in The New York Times. So why is disappearing so popular? There’s definitely an awkwardness to telling someone you’re not interested, but you can get past that with just a little etiquette:

  • Before a Date:

At least make contact to cancel. If the excuse is a lie, don’t just stand the person up, that sucks.

  • After a 1st Date:

It’s awkward to let someone know after one date that they didn’t entice you enough for a second. Since you can’t use the “it’s not you, it’s me” excuse, this may be the one situation where it’s understandable to just disappear. Plus, it’s not so hurtful after just one date.

  • Between 2nd and 6th Dates:

You owe them some sort of explanation, but you don’t have to get personal. You should call, but an email or text is marginally acceptable. Let the person know you don’t see a future together, but you think they’re awesome and wish them luck. Ghosting at this point will give you a bad rep and will sour what otherwise would be remembered as a nice couple of dates.

  • After 6 Dates… Until ‘The Get Serious Talk:’

There’s absolutely no ghosting at this point. If you’re ending it, you need to call and say something, anything. Even if you lie and say that you have been dating someone else and it’s become more serious, it’s better than ghosting. You owe them a phone call. You don’t need to engage in a conversation and don’t fall into the trap of why, how, when, who, etc. Just be respectful. More than six dates means you’ve been dating about a month or more, and that’s a substantial enough amount of time.

  • After ‘The Talk:’

Don’t pull a Charlize Theron like the article says and ghost on an official boyfriend or girlfriend. Just don’t do it. Bottom line: put yourself in the other person’s shoes and think about if you’d want an explanation, excuse, or even just a superficial apology… or if you’d be okay with never hearing from someone who you were interested in. Follow me on Instagram @howtowooajew

Dating Insights From Sukkot

by Caryn Alper under JDate,Judaism,News,Online Dating,Single Life

People are on JDate for a variety of reasons. Some people are on every dating site and app available; and it’s just one of many used to increase the number of people they meet. Others are on JDate because their mom threatened a nervous breakdown if they didn’t sign up. Others might like to find a nice Jewish person to date, but religion isn’t am absolute deal breaker. And still for others, their dating philosophy might be Jewish or bust. Whatever brought you here, we all have something important in common: we’re all Jews!

I know, I know, duh. This is JDate, not ChristianMingle or FarmersOnly. But, the holiday of Sukkot offers some interesting insights on why this is important. This week is Sukkot, a joyous Jewish holiday that celebrates our trust in G-d. We eat, socialize, and even sleep in a sukkah, which helps us remember how He protected the Israelites for 40 years as they wandered in the desert. One way we observe the holiday is by waving the lulav and etrog in all directions. In the grand tradition of Judaism, there is no shortage of commentary and discussion on the details of this mitzvah. But, I wanted to share one in particular that struck me as relevant to why we are all here on JDate.

The four species of plants (the etrog, the lulav’s date palm, myrtle, and willow branches) that we shake together are distinct and have their own meaning and symbolism, suggested by their fragrance and/or taste. (Why is it always four? Four sons, four questions, four cups of wine, etc.) One common interpretation for the four species is that each one represents a different kind of Jew, based on their levels of Torah observance and wisdom. I won’t go into the details of which is which, and all the specifics of the observance levels. But, the lesson here is that on Sukkot, we bind together the lulav and etrog and shake them all around us, symbolically binding together all types of Jews. The different kind and types are secondary — each Jew is important and we need all four types of species to fulfill the mitzvah of Sukkot.

So, you might be here because Grandma Esther threatened to sit shiva if you marry out of the tribe. But Grandma might be right — Sukkot teaches us that it’s important to stick together, and that every single Jew is an important part of our nation and our purpose. So, next time you dismiss someone because he or she has a different level of kosher observance or Jewish knowledge or family tradition, think again. These are important compatibility factors, but also, we are all Jews and should strive to be inclusive and accepting of each other.

Dear Tamar: Say No to Han Solo!

by Tamar Caspi under Date Night,Single Life


Dear Tamar,

Can you please advise women to stop wearing the Han Solo uniform on dates?

Thank you,

Chewbacca and Friends


Dear Chewy,


Okay, but really, I get it. Autumn is upon us, and with that comes a new wardrobe. I don’t know about you, but I’m not so sad to see the super short-shorts go away for awhile. I’ve seen enough tuchus this summer to last a lifetime! Fall clothing is nice because it’s not too baring and not too bulky. Regardless, women should make more of an effort for a date than just skinny jeans, boots, and a vest.

Ladies: you don’t want to shave your legs for a first date? Fine. So wear a dress or a long sweater over tights with booties. Show your prospect that you put in the effort and are excited about the date by dressing up a bit. It’s the least you can do. Save the Han Solo get-up (which I do love myself) for a girls night or a day at the mall.

Get more advice about first date etiquette in How to Woo a Jew: The Modern Jewish Guide to Dating and Mating.


Dear Tamar: Age Range in Your 20s and 30s?

by Tamar Caspi under Relationships

Dear Tamar,

I met a guy on JDate a couple of months ago and we’ve become nearly inseparable! It’s been amazing… except for one thing: he’s 5 years younger than me. It may be normal for the guy to be older, but not so much for the girl. Although it doesn’t bother me (he’s really mature and better than any guy my age or older that I’ve met in the past few years!), I think he’s starting to feel pressure because I’m turning 30 next month. I do want to get married and have a family and all that, but it’s not like my biological clock is deafening. I don’t want him to get freaked out now that I’m entering my thirties. He’s made a few comments here and there, and the friends and family we’ve introduced each other to have joked around about it. What do I do?

-JDater Turning 30


Dear JDater Turning 30,

First, many mazals on meeting someone awesome! I’m glad that you both were open to someone who likely wouldn’t fall within the generalized “preferred” age range for your age. A connection is a connection, and being a couple of years older or younger than who you “thought” you should date becomes irrelevant.

I think the best move for you is to confront it head on. Next time the opportunity presents itself, tell your boyfriend that you know your impending birthday might be freaking him out, but that it doesn’t change anything. Let him know that you’re happy where you are in your life, and in your relationship, and that entering a new decade doesn’t need to put any pressure on your relationship. You have to back up those words with actions and perhaps also politely let your friends and family know that the age jokes are not appreciated.

That said, you both do need to have a sense of humor about the fact that you’re a “cougar” at age 29 — and be able to laugh because you’re confident in your relationship, rather than cringe because you’re insecure in your relationship.

Follow Tamar on Instagram @HowtoWooaJew.

Dear Tamar: How Do I Ask for Romance?

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

Dear Tamar,

I fear mentioning my love of romance in my JDate profile because it may turn guys off. I am a hopeless romantic and I’ve tried to tamper that part of me, but it doesn’t work… it’s a part of me. I love watching and reading classic romances, and romantic comedies, and although I’m not expecting Richard Gere to climb up my fire escape, I think men get scared that I’m too high maintenance. All I want is some consistent flattery (that goes both ways!), and for the like/love to be shown as well as said. Why is it too much to expect a man to remember special dates, to make reservations more than a day in advance, and to stop and buy flowers on days that aren’t my birthday or Valentine’s Day or our anniversary? And how do I communicate this need?

-Hopeless Romantic


Dear Hopeless Romantic,

I personally don’t think you’re asking too much to a certain extent. Let’s start with how to express your desire for it before getting to what you should realistically expect.

Grab a thesaurus (or use your favorite wordy website) and find synonyms for “romance” and “romantic” so that you aren’t overloading your profile with words that may be equated with lovey-dovey, sappy, syrupy, fairy-tale fantasies. Instead mention — no more than twice! — that you are a lover at heart, you’re looking for someone to dote on who enjoys being affectionate as well, you believe in love, and so on along those lines. In the section about your ideal relationship you can mention wanting to find someone where you can’t keep your hands off each other and want that to last longer than the “honeymoon phase.” You can also simply say you’re a hopeless romantic, but that you’re feet are firmly grounded in reality.

Speaking of reality — life is not a rom-com and even the best of intentions are difficult to continue consistently. A man who brings you flowers every week may be running late one night and skip the tradition even though he enjoys watching you receive them, and then another night just be too lazy to stop even though he doesn’t want to stop making you feel special, and another night… life happens. And that’s okay. You have expectations, but you also have to be realistic and forgiving. It’s good that you mention being romantic in return; don’t stop doing that because you didn’t get flowers one week. If it makes you feel good to give, then keep giving, even if you aren’t receiving in return, otherwise it defeats the purpose and reduces the intent.

And remember that people view romance differently. One man may think holding your hand is hugely romantic! And it may be for him, and that should be appreciated! Other men don’t know what you mean when you ask for romance, so be specific because none of us are mind-readers. If you are happy with a date, but would like some more romance, then speak up and ask for it… nicely. If you’re already being romantic on your end, then it shouldn’t be too difficult for him to match that.

One last note: make sure you aren’t expecting too much romance too quickly and that you aren’t giving of too much romance too quickly. The former is unrealistic and the latter is overwhelming.

Want more advice like this? Buy How to Woo a Jew: the Modern Jewish Guide to Dating and Mating, available now!

Dear Tamar: My Ex Reached Out to Me On JDate… What Now?!

by Tamar Caspi under JDate,Online Dating,Relationships,Single Life

Dear Tamar,

I just received an email from an ex-boyfriend on JDate and I’m freaking out! It’s been 10 years… but he Broke. My. Heart.

It’s one of the few relationships I’ve never forgotten. At the time, I had to delete every remnant of him from my life so that I wouldn’t find an excuse to make contact; that’s how bad it was. But now here he is, still looking good. My knees buckled when I saw his name and photo, let alone that he reached out to me, asking how I’m doing and how things are.

So what to do I do?


Dear “Ex Emailer,”

This happened to me, but on Facebook. My pulse began racing and I broke out in a cold sweat upon seeing his name, and even felt a bit giddy that he had been looking for me! I hemmed and hawed over adding him, and initially did so he could see via photos how happy and fabulous I was without him! But, then he sent me a message and I was not interested in opening that door again… so I unfriended him and forgot about him.

With this scenario playing out on JDate it’s a bit different… he didn’t seek you out, but rather came upon your profile because you fit his search preferences and live in the same area. Him writing you an email is flattering, and you can do the polite thing and write back a brief email that is warm but also not too inviting. You don’t owe him anything, and that includes too much of your time. Don’t supply too much information and don’t expect much, if anything, in return. Many people — women, mainly, let’s be honest — have these fantasies that the guy who broke our hearts will return as our knight in shining armor, admitting that his biggest mistake ever was letting us go. That may happen in some sappy movie, but it’s not real life, so don’t get your hopes up. You moved on back then… continue to not look back.

Get more How to Woo a Jew on Instagram!

Do You Even Like Him?

by Caryn Alper under JDate,Judaism,Online Dating,Single Life

This year as the book is sealed, only G-d knows who shall live and who shall die; who shall get married and who shall remain single; who shall get a text back, and who shall get stuck checking their phone every two minutes in anticipation of a post-date call.  In this time of prayer and reflection, remember to ask G-d for what you want in the year to come.  However, be careful what you ask for – it might come true!

Allow me to explain: sometimes after a date or after meeting someone who asks for my number, I get in the habit of checking my phone more than usual. We’ve all been there – the post-good-date obsessive cell phone checking phase.  You know, when you bring your phone to the bathroom in case it beeps during the three minutes when you’re in there, when you’re glancing at it during work meetings, when you even restart it just to make sure there aren’t any missed messages that were somehow stuck in cyberland.

It doesn’t even matter if you plan to casually wait a calculated 37 minutes to reply – it’s your text, and you want it now! And in some cases, it doesn’t even matter what the message says or implies, or even what it doesn’t say – this game is about control. You’re playing a romantic game of phone badminton and the birdie is now in your court. You can make someone sweat if he’s into you by waiting too long to reply, you can end everything right there by not responding at all, or you can play games and be crazy about it by intentionally varying your response times or sending selfies or whatever else the kids do these days. The point is that as long as someone has texted you and the ball’s in your court, you have the control.

Let me be clear (said in my best Obama impression voice): I don’t advocate deliberate game playing, nor do I think it necessarily yields a good outcome. But, I bring this up to illustrate my longwinded point: after all this phone obsession, it’s easy to forget to ask yourself: do you even LIKE this person??  Have you even considered whether you would like to see this person again? Or are you just obsessed with the idea of keeping this badminton game going? Seriously, texting can become addictive, and it’s pretty easy to have no feelings for someone, but still feel excited at the idea of him, because, heaven forbid you go through a boring day at work without having a boy to text back and forth.

If this describes you, seriously ask yourself if you’re really interested in the person at the other end of the phone, or just the rush of the phone beeps and notifications you’re getting (or awaiting) throughout the day. Because if it’s the latter, and you’re seeking a relationship, don’t waste your time, the time of the other person (who might actually be into you – it’s not fair to him or her!), or your cell battery. Focus on finding someone you actually do like spending time with in person. On Yom Kippur and the upcoming yom tovs, practice living life without your cell phone glued to your hand – you might even meet someone in person.

Extreme Profile Makeover: “Barry”

by Tamar Caspi under JDate,Monday Makeover,Online Dating,Single Life

Hi Tamar,

My friend is cute and sweet, but not getting any attention on JDate. Can you take a look at his profile and see what you think?



Dear “friend” of Barry,

You’re right… your friend is cute and does seem sweet! So, let’s see how I can help your, I mean, his profile get more attention.

Let’s start with the photos. I like the main profile picture a lot, but do prefer more of a headshot for this photo rather than one where we can’t see his face (although I can tell that he is indeed cute). The other two photos are just okay, but would be better if there was that clear close-up of his face so that these were the fun complementary photos since they are both kind of dark.

Profile Name
Leaves something to be desired. Very typical “male” profile name of what is likely his last name and some digits. Barry seems to have much more personality than this profile name suggests.

In My Own Words
You know, there’s nothing here I would really change. I like what he had to write, which is why I think the focus needs to be on fixing his profile name and photos to support this. I would add a bit here and there… saying that your history is not “brief” can be seen as a sketchy answer since a 34-year-old should really be able to answer this without writing a book like the 62-year-old JDater who asked for an ‘Extreme Profile Makeover’ last week.

I can deduce by his tidbit about Philly sports teams that he’s likely from there originally — at the very least he can expand upon that and explain how he got to Los Angeles. This can either go in the “About Me” section or “Brief History” section. He also mentions not being able to live without his family, so he can also add which family members he’s close to so that dating prospects can begin to create a connection.

His Details
There are WAY TOO MANY blanks in this section, which only adds to the sketchiness I mentioned before. Too many blanks, unanswered questions, and too short of answers make it seem like the person is not really taking this seriously. Not everything needs to be filled in, but “My Ideal Match” needs more. What are his general preferences for a woman’s age? I suggest 25-35 for a 34-year-old man. Since he has his bachelor’s degree and says he’s established in his career, then he likely wants a woman who also has a minimum of a bachelor’s degree. He says he’s Reform and never goes to temple, so he should add those to the list as well.

Find more profile advice in the book “How to Woo a Jew: The Modern Jewish Guide to Dating and Mating” available now!