Archive for the ‘Date Night’ Category

Second Date Series: An Order to Ordering

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

When the time comes to order drinks and food on a second date, there are a few ways to proceed: You can either do it the generic way with each person ordering for themselves, OR you can use it as an opportunity to bond by ordering together.

If you both want wine, perhaps agree on one type and order the bottle. Or, if you prefer hard liquor, then consider doing a shot together (not too much to drink, you don’t want to lower your inhibitions or make yourself vulnerable when you’re not in a position to get your home safely).

When it comes to the food, discuss what you can order and share rather than having separate dishes. Try to be open to trying to new delicacies, and don’t be disappointed to skip your favorite dish in lieu of something you can enjoy together instead. You can have lasagna anytime, but you won’t have the chance to bond over digging into a unique dish and creating a new experience together.

If you are more like a Joey from Friends and can’t share your fries then please try to at least share dessert. Liking – or hating – food together is a bonding experience and will create memories for you as a possible couple.


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Second Date Series: Picking the Appropriate Place

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

Second dates are still not the right time for going to see a movie, live theatre, comedy show, or concert. You should pick another location where you can get comfortable and have a conversation. Find a locale that is both unique (to show you made a bit of an effort to choose something because you’re excited about the date) and informal — because you want to create a relaxed atmosphere to begin getting to know each other better.

It doesn’t have to be super expensive, but it shouldn’t be such a loud place that you can’t hear each other. And ideally this date occurs within a week from of the first date!


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Second Date Series: How Do You Like Me Now?

by Tamar Caspi under Date Night,Relationships,Single Life

While you’re on a second date, your conversation should start getting deeper and deeper (as well as on your third and fourth dates). This is not just superficial conversation; you should be asking questions and discussing more in-depth topics. To find out if you enjoy the same topics, you can mention them and see what reaction you get: A blank stare? An eye-roll? A passionate debate?

If you like world events, mention the Iran Deal, Greek’s economic collapse, or ISIS. If you enjoy science, then mention global warning or stem cells. If you love entertainment, then bring up the recent Emmy nominations, Amy Schumer, and anything else trending. If you’re passionate about politics, then broach the topic of Donald Trump and then the dozen other Republican candidates. If current events get you going, then bring up the topic of racism and if police are using unnecessary force. And of course, there’s sports… but that’s an easy one.

You may find that you cannot see yourself with someone who doesn’t read the newspaper, or someone who only gets their updates from TMZ, or someone who’s politics differ too much to understand, or whose schedule revolves around SportsCenter. Differences are good, but you need to have respect at the core in order to have a healthy debate. If you do decide to enter into a debate during a date — which is fine — be respectful and don’t hurl personal insults or allow it to upset you. If that happens, then you likely have your answer about the fate of the date. Remember that looks fade, but the ability to have enticing conversation can last forever.


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Second Date Tips: Seasoned Greetings

by Tamar Caspi under Date Night,JDate,Single Life

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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Second Date Tips: Series Starter

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

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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Happy Birthday!

by Caryn Alper under Date Night,Online Dating,Relationships

My birthday was last week.  This is exciting only because it means I got to identify the most random Facebook wall-writer of the day. That’s a funny thing about birthdays in this era: it’s the one day a year you hear from people you barely know — your preschool bestie, someone you met once eight years ago on vacation, your old roommate’s cousin, a great aunt who is new to Facebook and now invites you to play Candy Crush every day, and sometimes even strangers. This year, someone I don’t know even enthusiastically wished me happy birthday on my wall! Conversely, I have friends I see regularly who don’t really acknowledge birthdays — it’s just not a big deal.  In some friendships, we’ve established an unspoken rule that we don’t exchange birthday gifts or really acknowledge the day. And that’s fine with me — no one gets mad — that’s just how it is.

My point is that there’s a lot of variability in how people acknowledge and celebrate birthdays. So how are you supposed to know if and how to acknowledge the special day of a brand new significant other? If you just started to date someone new, do you even mention your birthday? What if you don’t know if you’re exclusive yet — does it matter? What if you get him a birthday gift, but he doesn’t want to go out with you on his actual birthday? Is a surprise party out of the question? To avoid all these issues, you should probably plan to break up with this person right before either of your birthdays is approaching. You can get back together afterwards.

Kidding aside, this can be a tricky occurrence. So I’d recommend being honest and taking cues from the other person. If you’re a cake, ice cream, and presents-kind-of-person, say so! Assuming you’ve been out more than a couple times together, it can’t hurt to mention that your birthday is coming up and express your expectations.  Unless your expectations involve extravagant gifts or selfish demands. Then it could hurt.

However, if you like this new person, and you want her to be part of your birthday, invite them along to whatever you have planned.  If you’d rather spend your birthday solo, curled up with a book, that’s cool too!  Just tell your new significant other, so he or she doesn’t try to plan a surprise party.  And if you’re expecting a big deal, don’t say it doesn’t matter how you spend your birthday, because you’ll only wind up disappointed.  And don’t be offended if your new beau or lady excludes you from birthday plans — it could be that there were no plans at all, or they might want to do something really low-key with close family.

Oh, and a final note: if you do have a date on your birthday, please wear something other than your birthday suit!

First Date Tips: No Expectations

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

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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First Date Tips: Don’t Analyze Everything

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

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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Be There in Five…

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

There comes a pivotal moment while waiting for a date to arrive at which point you have to make the official call: you’ve been stood up. This moment differs from person to person – some people might give up after waiting fifteen minutes, others thirty, or even an hour for some.  Or you may be in the George Costanza camp and wait about five minutes, after which you eagerly go home, change clothes, order food, and bask in the glory of eating dinner in front of the TV in your underwear. (Wasn’t it George who said something like, “I never met an obligation I was upset to get out of!”?)

No matter your personal tolerance for tardiness, being stood up is no fun. But, how do you determine if someone is just really late, or if there is a legitimate emergency, or if they just aren’t coming at all? If you’re the one running late, how far in advance do you inform your date? If one party is running really late, at what point do you decide to just cancel or reschedule? If someone has a good excuse for being late or not showing up, do you give him/her another chance? As usual, I offer more questions than answers. However, here are some general guidelines:

  • I generally give people a ten-minute leeway without question, but I tend to run on the late side myself, so your tolerance may vary.
  • If you are going to be more than a few minutes late, inform the person who is waiting for you and apologize when you arrive.
  • If you’re waiting on someone who is 5-10 minutes late, try not to make a big fuss about his/her unpunctuality on the first date. Stuff happens – be forgiving. But if it happens continuously and it bothers you, speak up!
  • If you are going to be 20 or more minutes late, you better have a decent excuse (or make one up). Call your date, explain, and offer to reschedule if he or she prefers.
  • If you’re waiting on someone who is significantly late, call and/or text to make sure you correctly communicated the same date, time, and location. It’s definitely possible that one of you showed up at a different location of the same place, for example.
  • Waiting on someone longer than 20 minutes consistently? Possible grounds for dismissal.
  • In the event that you get a better offer on the day of the date (or on the way to) and you decide to ditch your plans altogether, please inform your date. Say something came up. I suspect that this happened to me once – I was waiting for a guy to pick me up, and he never showed. After texting and giving him a ring, I got no response and never heard from him again! But don’t worry about his well-being – I could see that he was regularly logging in online and even updated his profile photos not long after that night. Harrumph.

Anyway, the point is: be considerate of people’s time. If someone isn’t considerate of yours, proceed with caution. And if you’re completely stood up? At least you can always spend the evening with an awesome, good-looking person, i.e., yourself.

Encountering Past Dates in the Wild: A Field Guide

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

The world is split between two kinds of people: those who run toward an acquaintance at the grocery store, eager to say hello, and those who dart away and hide in the next aisle in an effort to avoid forced small talk.  Which kind of person are you?

Do you fall into the same camp if the acquaintance is someone you previously dated? What if you recognize someone with whom you’ve previously changed messages, but you never met in person? What if the other person doesn’t recognize you? What’s the protocol here?

Relax, dear readers, I’ve got the rules below.

First, as a natural hider, let me say that avoidance is always an acceptable option.  On days where I just don’t feel like talking to someone, or I’m in work-out clothes with post-gym hair, or whatever, I’ve been known to feign interest in the nutrition facts of Worchester sauce until the perceived social threat has passed.  However, once you commit to the avoidance tactic, what would have been a 10-minute run to the store can easily turn into a tactical strategy of hard-core hide and seek.  Be forewarned.

But once eye contact has been established with the acquaintance, things get a little trickier.  Proceed as indicated below:

If you recognize someone who…

  • Is on JDate and you might be interested: Smile and make eye contact
  • Is on JDate and you are probably not interested: Avoid or smile weakly
  • You recently exchanged messages with: Smile and make eye contact
  • You exchanged messages over 6 months ago but never met: Avoid or smile, depending on whether you are still interested
  • You went out with once or twice: Smile
  • You went out with on the worst date of your life: Avoid — or, if you’re in a movie, make a loud scene resulting in the destruction of a pyramid of produce, causing innocent bystanders to start tripping over oranges
  • You dated for a few months: Smile and wave politely, depending on how things ended
  • You dated for a substantial amount of time: This really depends on the nature of your relationships, but given its length, you will know what feels most comfortable
  • Is a random, cute stranger: Smile! And ask for a food recommendation  – why not?

If you’re ever unsure whether to approach someone whose relationship isn’t listed above, come find me for consultation – I’ll be the one hiding behind giant sunglasses pretending to inspect the melons really closely.