Dear Tamar,

I’m turning 28 this year and have never been in a serious relationship… in fact, I don’t have any dating experience at all. I’ve always had my nose in books to be honest, and didn’t really have high self-esteem growing up. Now I feel like I’ve come into my own. After being in school for the past 25 years and collecting some really impressive degrees — and now gaining some pretty substantial success in life — I am ready to put myself out there. The problem is, I don’t know how to present the fact that I’m the real-life version of “Never Been Kissed.” Help!

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Dear “Never Been Kissed,”

Congratulations on all your successes, and especially on gaining self esteem! That’s awesome! You do not need to talk about your lack of experience in your 100hookup profile, nor do you need to discuss it with dating prospects. You can simply state that you haven’t been in a serious relationship because you haven’t found anyone worthy while you were busy working hard to achieve your dreams.

Meanwhile, I suggest you accept every date invitation you receive in order to get some practice. Once you get more serious with a specific suitor then you can perhaps let him know more about your lack of experience. Any man that really likes you won’t care… and if he does, then good riddance!

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It’s natural; in fact, it seems to be in our DNA as Jews to overanalyze everything. It’s not one of our better stereotypes, and when you add dating into the equation, it can create problems. It’s a twofold issue:

1. You’re reading too much into everything your date says (and does and more), and likely blowing things out of proportion.
2. Meanwhile you aren’t tuned in or present because you’re spending too much time analyzing everything.

It’s understandable to be cautious, or to have a hard time trusting immediately. However, it’s unnecessary to doubt everything your date tells you. Relax and enjoy yourself. If you continue to date someone for a while, then many questions will likely organically be answered over time. You can also simply ask for answers to any questions you may have when the time presents itself.

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Dear Tamar,

I had a 100hookupr send me an email (he was not my type, and not someone I would want to go out with), but I want to respond to the email as I think it rude not to. He asked me specific questions from my profile. Please help on how I can respond nicely, but let him know that I am not interested without hurting his feeling.

Thanks!

-Polite Rejection

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Dear Polite Rejection,

It sounds like your prospect has read my tips on how to write an awesome first email! The flip side is what you’re experiencing — getting that really great email and still not being interested, but wanting to show appreciation for the effort. And that’s exactly what you should write:

“Thank you so much for your email… I can see that you put a lot of thought into it and I really appreciate it. Unfortunately I just don’t think we are a match. I wanted to make sure you knew that the effort you put into the email didn’t go unnoticed, but I also didn’t want to leave you hanging. Best of luck to you in this crazy dating world!”

Play around with those sentences so that it is authentic to your voice. Recognizing the effort and adding a bit of humor at the end will help soften the rejection.

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Dear Tamar,

I am a 65-year-old widower and recently had instant chemistry with a woman. Within days we felt like our relationship was a comfortable old shoe.  The relationship grew quickly — she told me to slow down — I didn’t.  After a few weeks and a few warnings, she terminated the relationship by email.  She refuses to talk or give it another try.  How can I woo her back?

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Dear Burned,

I suggest contacting her the same way she broke off the relationship — via email. But first, make sure you truly comprehend what happened to bring an end to the relationship and take ownership of it. It seems from your letter like you understand that she asked you to slow down a number of times and that you didn’t listen, but don’t make excuses to her as to why you didn’t listen.

This letter needs to be about all the amazing things you like about her and how she makes you feel and how you hope to make her feel. Don’t make it all about you; if you want her back then it has to be about her — you already made it about you when you ignored her warnings and kept moving quickly when she wanted to slow down. You need to show her that you now understand where she’s coming from and offer to date her rather than jump back into a serious relationship. She may not want to though and you will have to accept that, but it’s worth a try!

After a first date what is the appropriate follow-up?

• If the date went well and the man paid, then the woman should call the next day to thank him for a nice evening. Don’t linger on the phone though, steer the conversation towards when you will speak again or when you will see each other again. A text can sometimes be okay here if you know he has a busy morning; just make sure that it has a flirty tone so he knows that you aren’t blowing him off.
• If the date did not go well and the man paid then the woman should text the man a thank you. Keep it simple and short. Make sure it’s not flirty so that you don’t lead him on.
• If the date did not go well and you split the check, then you don’t necessarily owe your date a thank you… but it’s good karma to say thank you and wish the other luck.
• If your date did go well and you split the check, then you should absolutely follow-up the next day with a call to let your date know you want another date
• If the date went well and you are the man who paid, but you didn’t hear from the woman, then don’t write her off just yet. Don’t assume it means she wasn’t grateful or doesn’t want to see you again. Call her and see where that leads.

All in all, if you want another date with this person, then how can it hurt to call — or even text — the next day? Do it. Pick up the phone and call.

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As your date comes to an end and you’re saying goodbye you may start getting nervous about what to do… handshake, hug, kiss, full-on make-out session? What should you do (or not do) to make sure you’re sending the right message?

Let’s operate on the assumption that the date went well — you’ve enjoyed each other’s company, so before bidding adieu: discuss plans to see each other again, thank each other for a nice time, and express how nice the date was. Then… go in for a hug while being open for a kiss without seeming to eager. That means having open body language and leaning towards your date with a smile and making eye contact. If your date returns those same signals then a short, closed-mouth kiss held for a few seconds is likely welcomed and will be reciprocated.

And if your date didn’t go so hot, well, there are even a few different scenarios within that area. If there wasn’t chemistry, but you still had fun, then give the hips-out hug. If it was just not-so-great, then a handshake will do. And, if it was awful, then a wave while saying thank you will suffice.

(And of course, I must address the dates where there’s lots of chemistry, but you don’t see a future… in that case, go in for the full-on make-out session and have fun!)

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You’ve made it! Another first date is coming to an end and yet the most uncomfortable part of the date has yet to occur: paying the bill. There are two scenarios depending upon how the date went:

Scenario 1
The date sucked. You know you don’t want a second date. The end of the date couldn’t come soon enough (even if things are “nice” you don’t want to waste anymore time) and finally the waiter brings the bill. You both reach for it. Your date is shocked that you’re reaching for it too. You offer to split. Your date is stunned. What do you say? Simply say: “I just think it’s right, but thank you for a nice evening.”

Scenario 2
The date went awesome! There was comfort, conversation, and chemistry! Neither of you wanted the night to end, but the restaurant was closing down and the night was late. The waiter brings you the bill, lays it on the table, and leaves. You both look at it because you don’t want this situation to become awkward when things have been going so great. Ideally, the man should take the bill and say, “It’s my pleasure to treat tonight and I hope there are more opportunities in the future for us to both treat each other.”

A couple extra tips:

• Pick a restaurant where you know you’ll be able to cover the bill.
• If you really want to impress your date, pull out all the stops and arrange to have the bill paid for before the check even arrives. Slip your credit card to the hostess or server whenever you get the chance.
• If your date does pay, then you must make sure you express gratitude and don’t take it for granted.
• If you’re going to make the motion to pay or split, then you better be able to follow through; don’t pretend to offer if you can’t back it up.

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After playing the 100hookup 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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When you’re planning a first date the biggest question is whether or not to commit to a meal versus just meeting for drinks. Well, I have the perfect solution! Make plans to meet at a restaurant that has a bar… and make reservations for dinner at that restaurant about an hour after you are to meet. If there is chemistry and conversation during the drink portion and you’re interested in getting to know your date more, then go ahead and follow the hostess to your table. If you don’t want to continue the date, then thank your date for his or her time and leave.

That said: you must check-in with the hostess ahead of time and let the restaurant know that the reservation is contingent upon the date going well and that you may end up canceling. Arrange a gesture or look that you will give the hostess if you want them to come and get you when it’s time, or not. (Or you can also walk-in without a reservation and if you are enjoying your time at the bar then go over to the hostess stand to ask for a table. If the wait is too long and you still want to stay, then order food to the bar.)

It may sound like a big hassle, but it solves a lot of issues about how to plan a date when you aren’t sure if you’re going to like the other person. You want options and you want to eliminate awkwardness. If you’re unsure when the time comes to go to your table, then take the plunge and sit down for dinner — sometimes people have nerves and the transition to the next stage of the date should help.

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Seriously, sometimes you need to just stop talking. It’s easy to get on to topics that are not really first date material — you’re vibe-ing and finding commonalities and having nice rapport, and it’s awkward to stop a conversation that’s flowing even when you know it’s not appropriate. So try and avoid the following topics and prevent the conversation from going there, before it gets to that point. This is a brief list:

• Exes: husbands, wives, fiances, boyfriends, girlfriends (stating when your last relationship ended/how long it lasted, how long you were married/when you got divorced is fine, just no details as to why it ended)
• Death: you just lost your grandmother, and that is awful, but it makes you sad… so perhaps don’t mention it. If you must, just don’t expand upon it
• Drama: with your job, family, friends — Do. Not. Go. There.
• Talking sh*t: whether your date knows who you’re talking about or not
• Finances: ’nuff said

Of course there are other topics that are personal to you and your story that you may not want to share. Joke about topics that are off-limits and say that you’d love to talk more about a topic if and when you’re on a future date. There are so many more positive and engaging topics you can talk about without bringing up too much about your past, or bringing in too much negativity.

It’s perfectly acceptable to briefly mention when your last break-up occurred, or what your political affiliation is, or to play hookup Geography for a minute, even if you find you have people in common you don’t like (see “talking shit” above). Make sure you are listening to the answers after you ask a question because that should organically keep the conversation going and not turn it into a job interview.

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