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.

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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.

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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.

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Dear Tamar: What Went Wrong?

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

Dear Tamar,

For the first time in a long time I finally liked a guy and we had a few awesome dates, after which he and I emailed and discussed making plans… but then I never heard from him again!

What went wrong?


Dear ‘What Went Wrong,’

That sucks. It seriously is the worst part of dating. I hate when people do that (it’s not always men, women are just as guilty); it’s rude and inconsiderate and simply not good for karma! So, here’s the way I look at it: this guy did you a favor by cutting out after only a few dates because he is clearly not who you thought he was, and is not the right guy for you. It’s not personal. It’s more a reflection of who this guy actually is than anything about you. It stings to not have closure, but chalk it up to him saving you from more grief later on and move on. And know that you are in good company because EVERYONE has had this happen to them… now make sure you don’t do it to someone else!

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Running Into a JDate While on a JDate

by Tamar Caspi under Date Night,JDate,Single Life

Dear Tamar,

So I follow your advice and I am poly-dating! Last week I went on a second date with a guy I met on JDate and it went great! Then over the weekend I went on a second date with another guy from JDate and WHOOPS… we ran smack into my other date (who was not a date).

I tried really hard not to make it awkward, and even introduced the two before excusing myself and that night’s date politely. It was easy enough to tell the guy who I was on a date with that it was just a friend we ran into, but the other guy knew better and I haven’t spoken to him yet. Obviously after just two dates I’m not in an exclusive relationship with either guy, but I also don’t have stronger feelings for one over the other because I barely know either. Now what do I do?


Dear JDate Poly-dater,

You said it yourself — it’s just the second date with each guy and you don’t owe either of them anything. That said, it would be best to address what happened and be straight forward with the first guy. Call him and just say, “Hey, that was kinda awkward!” Then ask him if it bothers him and see what he says.

He may understand that it’s early on, and not a big deal, and he may also be poly-dating himself. Or he may want to know if there are feelings on either side and how long you plan on seeing other people. Obviously you don’t need to divulge too much, but you can simply explain that you are looking for things to get serious with one person and that you don’t want to rush it.

He may not want to date you anymore. If so, it’s not personal. Even people who are okay with the idea of poly-dating can’t handle when it’s staring them in the face.

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Marriage Material

by Tamar Caspi under Online Dating,Relationships,Single Life

One of the weirdest things about dating is that we often date — and even stay in a relationship with — someone whom we can’t even imagine marrying or spending the rest of our lives with. We fight to make these relationships work and are upset when the other half of the equation sees the writing on the wall first.

Some of this is pride. We want to make it work with someone just so that we aren’t alone. Or to make it work with someone who is good on paper, or someone we think (or others think) we should be with. And we fight to make these relationships work because we don’t want to go through another breakup. And we are sad if the other person ends it first because it’s a bruise to our ego.

So here’s my straightforward, no bullshit advice: YOU KNOW this is not someone you want to or could spend the rest of your life with, so why bother spending one more day on this person when you could be spending that time finding someone better-suited? If you are looking conscientiously, then you know who you are and what you want in a mate and who you want to be in a relationship, so don’t settle or waste any more time once you figure out that person isn’t it.

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Watch and Learn

by Caryn Alper under Date Night,JDate,Online Dating,Single Life

Somehow in my mind, shopping for a new watch is equated with shopping for a husband.  Allow me to explain this thought process through a journey to the center of my mind: I’ve always been a watch person – I feel naked without one, and I’ve worn several different timepieces throughout my adult years.  And I tend to be more of a “quantity over quality” watch owner, preferring lower quality, trendier  pieces to classic expensive timepieces that will last forever.  A consequence of this habit is frequent replacing – straps break, batteries fail, faces tarnish, and in one case, this chain attached to the strap that I thought was really cool just plain fell off. My penchant for replaceable (read: cheap) watches means I’m always on the lookout for the next style I might want to wear. So whenever I’m shopping at a department store (or let’s be honest – Marshalls and/or TJ Maxx), I usually peruse the watch section so that when my current watch inevitably breaks, I’ll have a replacement in mind. One store in particular usually has a ton of good options for sale, and I never have trouble finding several that I like when I shop.

So anyway, a couple weeks ago, my watch battery died, and soon after, I realized that water droplets had somehow snuck under the glass that protected the face of my watch, rendering it unreadable.  The situation wasn’t worth fixing, so I headed to my favorite store to find a replacement.  But something different happened. Now that I actually had to pick one to buy and wear everyday on my wrist, I suddenly couldn’t find one that I liked! Just a few weeks prior, when I wasn’t seriously in the market for a watch, I saw a display of nice watches, any one of which would look nice and have the features I wanted.  But now that I actually had to choose one to wear, all I saw were flaws.  This one was fine, but I really wanted a leather wrap-around band and this wasn’t exactly what I pictured.  And that one had a nice face, but the band was a rose-gold color that clashed with my other jewelry.  This inner dialogue went on and on until I couldn’t find a single watch that met my expectations. So I left the store, defeated.

And then, standing there empty-handed in the mall parking lot, I had a mini-epiphany: This is exactly why I leave so many dates “empty handed.” The same psychological principle is at play here.  When I look at a group of something (watches, people, whatever), I see a general sense of possibility – a pool of potential. But selecting one out of the group means leaving other (possibly better) options behind, or picking the one that will turn out to be a lemon, or deciding that one is best, only to have your tastes change shortly after selection.  A watch is just an object, and especially for me, it’s not a permanent life fixture. So if I felt that way about my watch selection, it’s no wonder these thoughts and the related fear cause me to “leave the store” of dating without selecting an option.

So back to the story – there I was, watchless. I decided to go to a different store and check out the selection, and I found the same issue – lots of choice, none perfect. It was getting late (I think – I didn’t know what time it was) and I didn’t want to go home empty handed. So I picked the least objectionable option and called it a day. And you know what? I’m really happy with my reliable new watch. I now like the way it looks, and it runs great.  A stylish coworker even complimented it.

So the next time I find myself surrounded by options of people, yet feeling disappointed and ready to leave, I hope I remember to glance at my watch – it will tell me that it’s time to change my thinking.

“In My Own Words” — Vague or Detailed? That is the Question.

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

I’m not sure Jewish scholars such as Maimonides, Hillel, Akiva, or Rashi would be able to agree on whether it is better to have a vague ‘In My Own Words’ answer… or a more detailed one (they didn’t agree on much, so it’s not surprising that our people are known for our argumentative nature).

On one hand, a vague About Me (or any other category) is enticing as it leaves more for your date to discover on their own and allows you to let them discover more about you at your own pace. You get to reveal more about yourself in your (few) emails, a bit more in your (10 minute) phone calls, and even more in person. You’re not putting everything on the table, and that means you don’t have to live up to any hype you create if, for instance, you are really funny with your writing, but not so much in person.

On the other hand, being more detailed in your biography means that the prospects you attract know exactly who you are and what you are attracted to — more than just your photo and a few general tidbits. It means you have likely weeded out potentials who you may not mesh with, but it also means that you could have eliminated quality prospects who think you are too set in your ways… even though it’s not only acceptable, but more enjoyable to not agree with each other about every topic.

So here’s where your How to Woo a Jew scholar gets to butt in and give her two cents… I suggest a happy medium. Some areas you can stay vague while others that you feel more strongly about should be more detailed. If you are sarcastic and witty in-person, then try to convey that in your biography. If you love debating politics, then say that as well but also mention some particulars — if you are a staunch Democrat and couldn’t bear to be with a hardcore Republican, then let that be known! Areas where you are open to exploring should be left vague or simply state that you want to learn more from someone who is an expert or enjoys those things.

Basically there’s no “right” or “wrong” way because everyone has a type, and the person for you won’t be turned off by your vague or detailed profile… the caveat here is that if you’re having trouble meeting quality prospects, then it would behoove you to adjust your answers towards the other side of the spectrum.

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Revisit Your Vision

by Tamar Caspi under JDate,Online Dating,Single Life


Growing up we all had dreams of how we saw our lives unfolding. We pursued the things we had control over, and worked hard to try and put certain things in place. But finding and falling in love is not necessarily something you can check off of your list so easily. That’s not how life works. Love is messy.

But, giving up that vision is difficult and can prevent us from seeing other — likely better — options standing right in front of us because we are so stuck trying to achieve the picture in our head of how it is supposed to be. That means being open to new things, things that may make us slightly uncomfortable at first, and playing around with that “preferences” section rather than simply inputting exactly what we think we want. You might find yourself happily surprised!

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A Contradiction in Terms

by Caryn Alper under Date Night,Online Dating,Relationships,Single Life


Have you ever realized how many famous adages or proverbs actually contradict one another? Within the last two blog posts, I advised you to be less picky when dating, yet not settle. Don’t discount people too quickly, I said, yet don’t force a connection if it’s not there.  All of this sounds like reasonable advice. But, which is it?  You can’t have it both ways, right? I guess the good news with conflicting information is that you really can’t go wrong either way, since someone says it’s right. This got me thinking about other instances of paradoxical advice – they are more common than you might realize! Which of the examples below is your favorite?

  • Absence makes the heart grow fonder vs. Out of sight, out of mind
    • Favorite sayings of long-distance romances everywhere, these two basically provide opposing advice. There have been different times in my life when both of these have been true in different situations, but you might as well focus on whichever you want to be true, because they cancel each other out.
  • Love yourself as you are vs. Always strive to improve
    • The essence of this contradiction is often found in women’s magazines – the messages “love your body!” and “you’re beautiful the way you are!” sound great until they are sandwiched between articles on how to lose 10 pounds in a month and how to get guys to like you by changing your hair and makeup. But these are not mutually exclusive – it’s possible to love yourself and want to improve, both internally and externally.
  • Play hard to get vs. Don’t play games
    • Ah, the classic debate – do you try to play it cool by calculating how often and how long to wait before responding to someone, or do you just do and say whatever you feel like doing and saying? Opinions vary and often conflict, as does conventional wisdom. Looks like the jury’s still out on this one.
  • Birds of a feather flock together vs. Opposites attract
    • I hear both of these sayings all the time – could it be that they are both true, to some degree? Maybe we tend to flock together with people who have similar interests, goals, background, and values. But an opposite temperament or personality brings a little spice to life.

The moral of the story is that no dating advice is ALWAYS true in ALL situations. So be judicious when taking well-intended dating advice from people who don’t know your particular situation. But also remember that wise men think alike… but fools seldom differ.