Dear Tamar,

I am back on 100hookup after about a year off and already met a great guy! He and I exchanged a few emails, and now a few texts. He sent the last one last night. So what next? What do I do?

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Dear What Next?

Do nothing. If he wants to go on a date with you, he will call you and ask you out. I am not a fan of texting, aside from exchanging pleasantries, before you’re in a bonafide relationship. We’ve all heard the phrase “he’s just not that into you,” and here’s where it rings true: If a guy is into you, he will call and ask you out, otherwise he’s just not that into you.

UPDATE
Since initially writing this, the guy did, in fact, call and ask our lovely emailer out!  They went on an awesome first date and they already have their second date planned!

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I don’t know about you, but I easily went on 100 first dates and only a handful of second dates. That meant that I was excited and nervous prior to a second date, because they happened so seldom! As I approached my date, I wondered… what is the appropriate greeting here? Just smile? Hug? Kiss? Luckily, there is a pretty simple answer.

As you walk up to your date you should do whatever it is you did to end your first date, plus a little extra. What does that mean?

• If you left by standing and smiling and waving, then keep that smile going but add in a little hug
• If you left with a hug, then hug again but add a kiss on the cheek or hug a bit longer and include a squeeze
• If you left with a kiss, then kiss again and allow the kiss to linger just a bit longer
• If you left with MORE than a kiss, then definitely kiss again to start this date

You both know that it wasn’t easy getting to a second date with someone — you liked the first date, you’re interested in learning more, and there’s attraction — so you want the other person to know that you’re excited without coming on too strong. You also still don’t really know this person and are understandably anxious for it to go well, by being prepared with how you’re going to greet each other then you will be able to get past the first hurdle quickly and move on the date with ease.

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I’m pretty sure I covered every aspect of a first date with my First Date Tips series (click on these links if you need to catch up: Go Together or Meet There, Patterns, Confirming Plans, Don’t Talk About That, Ease On In, Conversation Starters, Paying the Bill, Saying Goodbye, Post Date Follow-Up, Don’t Analyze Everything, No Expectations). But… what about the second date? Just because you chose to see each other again doesn’t mean you’re not nervous!

Second dates (and third and fourth dates) should be treated a lot like first dates in regards to having some level of formality… and with a certain amount of hesitancy. You still don’t know this person very well, you still shouldn’t be texting, and you still shouldn’t be engaging in any other social media (no Facebook friending yet!). You should still be making the effort to plan dates, and putting extra effort into getting ready, and be practicing the same conversational tips as your first date.

I’ll be going more into detail about what this all means in the coming weeks!

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We all have mental checklists of expectations for new prospects, which can sabotage a date when they aren’t met. Some of these expectations include:

• Calling to confirm the day of or day before
• Making reservations/being easy-going about planning options
• Arriving on time
• Looking as though you put effort into your appearance
• Asking questions/listening to answers/participating in conversation
• Showing consideration while ordering
• And so on…

As the lead-in to the date and actual date progress we tend to tally when a prospect does or does not achieve these benchmarks, and then begin judging the prospects based on these expectations… effectually taking us out of the date. When you do this, you’re not present in the date or giving a prospect a fair chance.

Try to appreciate each date for what it is and enjoy your time. It’s also difficult not to compare one date to another, especially when you’ve been on some amazing dates that may have set a high benchmark, but each date needs to be treated as a unique entity. After all, there’s a reason you’re still dating and not in a relationship with the prospects that set those benchmarks!

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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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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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