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 100hookup and it went great! Then over the weekend I went on a second date with another guy from 100hookup 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 100hookup 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.

Follow How to Woo a Jew on Facebook, Instagram, and Twitter!

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.

Follow How to Woo a Jew
on Instagram
on Facebook
on Twitter

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.

I’m not sure hookup 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.

Learn more at www.HowtoWooaJew.com.

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!

Follow Me!
Instagram
Facebook
Twitter

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.

Last week Bravo! TV’s The Millionaire Matchmaker Patti Stanger announced that she and her boyfriend of three years had split up. Patti got ahead of critics who would doubt her abilities as a matchmaker when she herself can’t seem to find a forever mate. And her statement is spot on:

“I’m a human and I own my issues… But that doesn’t change the fact that I’m incredibly good at my job. I excel at setting people up and helping them fall in love. Look, how many Pro Football Hall of Fame coaches have scored touchdowns in the Super Bowl? Coaching people into winning the big game is a different skillset than winning the big game yourself. I’m really good at being a love coach. In fact, I’d say I’m one of the best. But, at playing the love game myself? I’ve got some work to do and I’m chipping away at it. I know I’ll win my game soon, but until then, I’m going to keep being the best coach I can be.”

It reminds of the phrase “those who can’t do, teach,” and that’s exactly what Patti is doing. She can see the issues other people have and helps them to work on them while finding partners who would complement them — all the while she admits that she herself is a work in progress, setting a great example that none of us should ever stop trying to better ourselves.

I myself have admitted that my divorce, as well as most of my past relationships, made me better at dispensing dating advice. Does that mean I know everything about relationships? Absolutely not. Does that mean my relationship with my fiance is perfect? No. But, admitting that is what makes me — and Patti — good at what we do.

Follow Me!
Instagram
Twitter
Facebook

When you go on a first date with a 100hookupr that you are super-excited about (as in, more than normal), it’s typical to pull out all the stops and do things a little more special than other first dates. Men could have flowers delivered to your date’s house earlier in the day, you could pick your date up in a chauffeured car when you normally would’ve met your date at the venue, you could make reservations at a highly sought-after restaurant rather than just grabbing drinks somewhere convenient, you could slip the waitress your credit card while on a trip to the bathroom, you could arrange for champagne to be waiting for you at the private booth in the back with rose petals strewn about, and you could leave your phone on silent and not check it all night. Women could arrange to get their hair done, have a facial, get waxed, nails manicured and pedicured, makeup professionally applied, wearing a new dress with height-appropriate heels, and act as though they are as easy-going and flexible as possible even though they are jumping out of their skin with excitement and anxiety.

Any or all of these things are bound to impress your date and leave them feeling incredibly special. Granted, you still need to fill the date with chemistry and conversation, but the wooing is well on its way. The problem? Unless you plan on repeating, matching, and upping your romantic gestures on every date, then you’ve set a precedent that will be difficult to match. And even if you do continue to roll out the red carpet then eventually real-life sets in and you will see each other without the shiny bells and whistles.

So here’s the conundrum: do you or do you not make that extra effort because you won’t be able to keep it going (no one can!)? You should make that effort, let the person know you think they are worth it! And once you’re sitting down and having flirty conversation you should simply come clean — “I was really excited about tonight so I took the time to primp/plan/etc., and I’m so happy it’s going well… just don’t expect me to look like I have it all together all the time!” Of course, that doesn’t mean you should show up to a date in your sweats after being snobby about the location.

If you like someone you should make some effort every time to show them that they are worth the effort. It takes five minutes to make a reservation so you don’t have to pick up your date and ask “So where should we go?” And it takes five minutes to apply a fresh face of makeup. These small acts let your date know they are special.

Follow me!
Instagram @howtowooajew
Twitter @hookuplove
Facebook.com/HowToWooAJew

Dear Tamar,

Could you kindly eyeball my profile? I’ve gotten plenty of emails and very few are viable. I’ve tried to convey that there’s a certain lifestyle that I’m accustomed to, don’t want to give up, (and am capable of giving myself), yet I don’t want anyone to assume I’ll take care of them too. I know, can’t have it both ways, huh? Perhaps you could tweak that part? I’d be very grateful if you could give it a quick once-over.

-“Karen”

____________________________________________________________________________________

Dear “Karen,”

I’ll get to the wording of what you want to convey about your lifestyle in just a bit, but let’s start at the beginning of your Extreme Profile Makeover.

I like you how you combined your name with a description — although I initially thought it was your first and last name combined (MAJOR no-no for security sake). In order to show that you’ve combined a few words without confusing prospects, try capitalizing the first letter in each word (i.e. instead of tamarluvsya it would be TamarLuvsYa, see the difference?).

You have some great photos to work with! Switch 1 and 2 and delete number 4 and then you will be good to go! Photo 2 shows you in a bright pop of color with approachable body language. Photo 1 is nice and shows your full body but it’s taken from further away. Photo 4 may be realistic, but it’s not appropriate for your 100hookup profile — you said it yourself by labeling it as a shot of you “tired.” Lastly, photo 5 is great, but don’t be surprised to get emails from men asking about your daughter!

In your biographical responses I don’t really see where you think it conveys that you live an indulged lifestyle and that men may think you’re a sugarmama (for lack of a better term). What I would suggest is maybe eliminating some Q&As. You don’t need to answer all of them because some of them are a bit repetitive and it comes across as overkill. Delete “My Past Relationships” since you mention your ex-husband in “About Me” and then combine and eliminate either “I’m Looking For” or “My Ideal Relationship.” And finally, eliminate “On Friday and Saturday Nights I Typically” and combine that answer with “For Fun, I Like To.”

Lastly, under Ideal Match I would consider narrowing your age range. A man in his late-40’s is a bit young for a woman in her late-50’s. Perhaps that’s why you’re getting men that you don’t consider viable. A man in his mid-60’s is a good maximum though. I would consider a 10-12 year age range, for a woman who is 58 that means around 54-66.

Good luck!

____________________________________________________________________________________

Follow me!
Instagram @howtowooajew
Twitter @hookuplove
Facebook.com/HowToWooAJew

Dear Tamar,

I have been dating this guy for a month; nothing serious — we went out for lunch last Monday, on Tuesday we exchanged a few texts and kind of made plans for Saturday… but he never confirmed and now it’s Thursday and I still haven’t heard from him.

What’s the deal?

_____________________________________________________________________________________

Dear Plans Unconfirmed,

The simplest answer is that it’s likely he’s not into you anymore. I know that sucks to hear, but a guy who likes you is confirming plans, contacting you between dates and wanting to make sure he is on your mind.

That said, it’s only been two days and he could still call to confirm plans tonight. It’s not too late for him to call for a Saturday night date, but if you accept… do so with your guard up. Or, better yet, tell him you made other plans when you didn’t hear from him, but would love to schedule something for next week.

Be prepared to not hear from him again, and then get back on 100hookup and keep making connections.

P.S. If he texts or calls next week I strongly urge you to ignore it (unless you just want to hook up), it’s likely he is only making contact because he’s bored and wants to see if you’re still interested. Don’t expect his feelings towards you to suddenly have changed; you’ll only end up disappointed once again.