Archive for the ‘Date Night’ Category

First Date Fashion Part II

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

Last week, I talked about some general dating fashion tips, but this week, let’s get specific. How do you know what kind of date calls for what kind outfit? Check out the list below for some guidance:

Coffee date: Asking someone for coffee means “you’re a decent online conversationalist, and I’m ready to meet you in person, but I’m not willing to commit to anything involving time or money in case we don’t click in real life.” Due to the casual and brief nature of the coffee date, you’re allowed to look casual. However, because of the brief encounter, your first impression is even more important here. This means that you should take care to look good and presentable, even if you’re wearing casual clothes. Do not wear gym clothes, leggings, or anything that shows you clearly stopped by the date on the way from an activity that involves sweating.  A sundress, jeans, or a sweater dress and boots in the winter is perfect.

Drinks and/or dinner: I put drinks and dinner in the same category, because, if a drink date goes well, it will often lead to dinner.  Assuming this dinner date doesn’t involve a drive-thru window, look extra nice!  Ladies, this means a dress and heels (unless your date is shorter than you, in which case, use your discretion), or something equally dressy. Guys, slacks and a shirt always work – and tuck it in and use a belt!

An “activity” date: This can include bowling, hiking, rock climbing, or any extreme adventure from The Bachelor that doesn’t actually happen in real life.  You will be moving around, so you want to be comfortable (i.e., not pulling up your strapless bra or tugging at your dress), but this is NOT an excuse to wear some ratty old gym clothes.  ‘Athleisure’ is a thing for a reason.  Leggings (in good condition) plus a bright colored top and tennis shoes will do for the ladies.  Guys, clean clothes without holes and tennis shoes in good condition are acceptable. You might decide to go to a casual restaurant afterward, so make sure your outfit is versatile.

Wild card: In this scenario, all you know is that you’re getting picked up at 8. You aren’t sure where you are going or what you’ll be doing.  Unfortunately, you must be prepared for a multitude of situations.  You should be safe wearing something on a level between your coffee date and dinner date.  Wear semi-comfortable shoes in case you end up walking more than expected, and for either gender, you can’t go wrong with nice jeans and a cool jacket.


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.

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


Dear Tamar: What Next?

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

Dear Tamar,

I am back on JDate 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?

______________________________________________________________________________________________

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!

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


Clean Up Your Act

by Caryn Alper under Date Night,Single Life

“Can I come in for a nightcap?” *Panic*  This question is a variation on “want to come back to my place?” and no more polarizing post-date words have ever been spoken. But, not for the reasons you might think. Inviting someone back to your place unexpectedly is a terrorizing thought to… someone who has a messy house!

Single people, i.e., people who are dating and might find themselves in such a situation, tend to live either alone, with a roommate or two, or with their kids, all of which are risk factors for living in filth. It’s pretty easy for me to go days without putting anything (including dishes or clothes) away, and this slothfulness was only compounded when I lived with roommates in the past.  So what to do if a new dating partner stops by or wants to come over without advance notice?

My dad always said, “How will you get a guy if your apartment is such a mess? What if he wants to come over? What kind of housekeeper will he think you are?” You know, something, Dad?  I think you are right.

Some housekeeping disasters just can’t be explained away, so your best bet is strictly preventative.  Improve your own life AND your likelihood of impressing a date by always keeping your pad in showable condition.

If you can’t bear to vacuum and dust everyday, here are the basics:

  1. Keep your bathroom presentable. Let’s say a guy is dropping you off at the end of an otherwise decent date, and he asks if he can come in to use the bathroom.  Because you were just getting ready for a date, there’s a good chance your bathroom looks like Sephora exploded on your counter, leaving a trail of strewn about hair sprays, eye shadow palletes, hot rollers, etc. all over the place.  Next time, when you are finished in the bathroom, throw all your products in a basket, get rid of stray hairs that always find their way into the sink, and put the toilet paper roll back on the holder, just in case!
  2. Always have a clean entryway or living room. If someone walks you in to your place, this is the first impression he or she will have. When you are getting ready to leave, take 5 minutes and move your mail, purses, shoes, and mountains of outfits that you tried on and didn’t wear and shove them into a closet.  Just don’t forget where you stash your stuff. This is frustrating. Ask me how I know.
  3. Make sure your kitchen isn’t gross.  If someone stops by or comes over, you will probably offer a drink.  Don’t be that person who can’t find a clean glass among a sink full of dirty dishes. Oh, and try to keep a hand towel for guests in the kitchen and bathroom too.

They say an ounce of prevention is worth a pound of cure, and when it comes to cleaning, a little bit of straightening up is worth it to prevent potential embarrassment!


When Being Truthful is Too Honest

by Tamar Caspi under Date Night,Relationships,Single Life

Last night I was at a bar with my sister and brother-in-law and I had forgotten to put my ring and other jewelry on after a day at the beach. So there I was, a third wheel, being hit on! Obviously it was good for the ego, but it was also good for the blog.

My first observation was how many more men were likely hitting on me because I wasn’t putting off an “available” vibe and wasn’t at the bar to meet men. So go out and have fun with your friends, and don’t worry about who’s around and who’s available. Sure you might be there to meet prospects, but you’re also likely at a bar with friends, maybe celebrating something, or just going out to have fun — and you should be doing that rather than focusing on who else is there.

My second observation had to do with one guy in particular, let’s call him Rider, who was honest to the point of awkward. After introducing himself, my brother-in-law began chatting with Rider about his career as an X-Games athlete. That’s when Rider told us that he is a former heroin and cocaine addict. Um… whoa! That’s a lot of information to absorb about someone we had just met 30 seconds earlier. I congratulated him on his recovery and quickly excused myself to find the waitress.

It got me thinking about what is appropriate to divulge when you first meet someone, or even later on a date. There’s nothing that Rider had to be ashamed about, but I’m not sure I needed to know that information quite yet. Even when you’re not dating but simply meeting someone, you don’t need to bare your soul. I’ve always recommended being upfront about your history without going into too much detail until you’re further along in a relationship, be it friendship or romantic.

Follow How to Woo a Jew!
Facebook
Instagram
Twitter


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.


More on Social Media while Dating

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

If you have a JDate account then I can pretty much assume that you have a Facebook page — and quite possibly some other combination of Instagram, Twitter, Snapchat, Google+, and/or LinkedIn (and I’m sure there are other sites and apps I’m missing). Using the internet while dating is tricky because once you exchange names, then all it takes is a couple of clicks of the mousepad to learn more about a prospect.

This is a good and bad thing, which I’ve discussed before, but that doesn’t mean you need to shut down social media. A guy I once dated was unsearchable, and it actually made me think there was something he was hiding. Even once we started dating and added each other on different sites — eliminating the “privacy” modes — he still didn’t have anything posted, nor did he often “like” items. He did, however, scroll through Facebook and Instagram regularly and the combination of the two made me very skeptical.

On the other hand, you can meet people who over-share and put every detail about their life online — pictures of their meals, status updates about their frustrating morning, opinions about everything, photos of every thing they do, and so on. That doesn’t include clicking “like” for ALL of their friends posts and commenting as well. It’s exhausting and it’s overkill for someone who barely knows you, but is interested in dating you.

As with most things, there’s a happy medium with social media where you let people see things about your life without being too much of an open book or too much of a recluse. You can also use privacy settings for people you don’t really know so they can’t see everything you post, and they can get to know you at a more natural pace.

That said, try not to cyber stalk and don’t add your date on social media until you’re on your way to dating seriously. Not every first date should become a Facebook friend.

Follow How To Woo A Jew
Facebook
Instagram
Twitter


“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.

Learn more at www.HowtoWooaJew.com.


A Contradiction in Terms

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

CRTV-2149-header-CA

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.


Second Date Series: Saying Goodnight

by Tamar Caspi under Date Night,Single Life

So how do you end a second date?

Well, it depends on if you want a third or not.

If the date went well and you would like to see them again, then you should share a kiss goodnight. If you ended the first date with a nice kiss, and greeted the second date with a nice kiss, then perhaps this kiss should linger and last longer. The purpose is twofold: to let your date know that you are definitely interested and to establish physical chemistry. But let it end there. This is not the time to extend an invitation to go home with you or to accept such an invitation.

If you don’t want another date then you should make sure to bid adieu respectfully and with dignity. Thank your date for a nice time and express your appreciation if the other person paid. Or… if you don’t want another date but there’s sexual chemistry then go ahead and have some “safe” fun! Safe both in a physical as well as emotional way: make sure to use protection but also make sure your date knows this is just a hook-up so that feelings are protected as well.

 

Follow Me!
Instagram
Facebook
Twitter