Dear Tamar,

Hi! I’m new to the whole online dating scene. Right now I am talking to two girls at the same time and I am not sure whether I should take them both out on dates or just one. Should I take one girl out on a date and stop speaking to the other girl even if I’m still interested in meeting both? Thanks!

Dear Two Timer?,

“Meeting” a girl on JDate does not a relationship make. I am a strong, strong advocate of poly-dating until it gets serious with one person. First of all, you may pick one girl and have no chemistry with her and now you’ve already ruined your chances with the second girl. Take them both out on dates, try to be unbiased and not compare them to each other, and save any decisions until after each date. There may be no attraction, no chemistry, or it may not be mutual with one or both of the ladies. Keep your options open at all times. Between when you “meet” a girl on JDate and when you actually meet her in person, you may “meet” even more ladies online… and guess what? That’s great! If you were able to meet that many great Jewish gals at a bar then JDate wouldn’t exist, but the fact is that you can’t; no one can, which is why JDate is so successful. Take the opportunity to meet as many women who fit your preferences as possible because the more women you meet the better your odds are of finding your Beshert. Good Luck!

It’s funny because, no matter how old I get, or how many dates I go on, after a really good one I always call my friends afterward to tell them about it. I don’t care how guys are supposed to act after a date, or what is perceived as “playing it cool” because if I go out on a good date, I will call my friends after to talk about it like an excited schoolboy. I mean, as human beings, it is only natural that after we have enjoyable experiences, we feel a strong desire to share them with those closest to us.

Recently, I went out on a third date with a woman that I had met on JDate; on the first two we had gotten along really well and both had a good time. Since we had met for frozen yogurt on our first date, and gone out for sushi on the second, I wanted to do something a little different for our third date. After thinking about our options for a Wednesday night, I asked her if she was game for grabbing dinner at this offbeat pizza place and then going to an Improv club for a show.

She responded that she was “up for anything” and we agreed on a time that I would pick her up on my way back from work. The pizza place was just down the street from the club so we grabbed some macaroni and cheese pizza (delicious), and chicken fettuccini alfredo pizza (yummy), before heading over to the show. The first act was a little a hit or miss with the performance since they were a newer group, but the second team more than made up for it and was absolutely, side-splittingly, hilarious!

After the show we talked for a little bit before I dropped her off and we said goodnight. However, by the time she made it inside her building, I was already dialing a friend to talk about the date. Once we got off the phone I quickly dialed another friend and it was after we hung up that it dawned on me that my wanting to immediately call my friends after a date was a sign that I was excited because it had been really great.

Undoubtedly, other people have different subconscious indicators that tell them they had a fun time. If you don’t know what yours are then I encourage you the next few times you go out on dates to think about what were your immediate natural reactions afterward. Often times, after going out on date after date, we try to fool ourselves into thinking that a date went better than it did. However, it is in these situations when we can rely on our post-date indicator to keep us grounded in reality by telling us the truth about whether or not it truly went well.

You are going to meet people on JDate. You are going to talk to the people you meet and, in some cases, you are going to have an extended interaction with them that leads to a date. In those cases, if you are like me, you’re going to get excited and eagerly anticipate that first meeting.

Depending on the particular situation, a first date might range from simply meeting for coffee to grabbing a nice dinner to even something more ambitious and unique like going to an exhibit or attending a concert. Even though each couple is going to make different choices regarding how they construct their first date, when it comes down to it, they’re meeting and that’s all really all that matters. Especially since getting to that first date isn’t always easy.

Many online conversations start out as promising but never seem to find exactly the right rhythm that keeps them going and elevates them to that next level. However, you can’t be deterred by this online dating inevitability (and others like it), and must stay the course by remaining active in trying to meet people. It is that attitude which ultimately makes that first meeting so fulfilling.

But what happens if the night before, or day of the big date, the other person cancels?

This scenario happened to me several times before I even went out on my “first” first date with someone I had met on JDate and I’ll be completely honest when I say it doesn’t feel good. No matter how legitimate the excuse sounds, no one likes to have the rug pulled out from under them, especially in a situation that they were looking forward to, and had put a lot of time and energy into setting up.

I’ve had women cancel on me for a variety of reasons, including having to babysit for friends, forgetting about a friend’s graduation they promised to attend, bad headaches and some others I can’t even remember anymore. However, in spite of the fact that some of these excuses were probably true, the point still remains that it sucks to be cancelled on.

Unfortunately having people break plans that you were excited about is a part of the online dating game and is, therefore, pretty much unavoidable. Putting up a profile on a dating website and thus proclaiming to the online dating community that you are single and looking to meet people is the first important step, but you need to stay committed and not dwell on the disappoints that pop up along the way. I promise when you finally get to that first date, and everything about it feels right and natural, you’ll be glad you didn’t let a few broken plans deter you from trying.

It is really popular for people, in general, to say that going to the movies is an awful way to spend a first date. But I think that going to the movies can be part of a great date. Please note that I am often wrong, and have been on many terrible first dates.  This being said, however, I stand by my ridiculous claim.

Of course, just going to a movie can’t be a whole date.  I do believe, though, that it can supplement dinner, or another imaginative, phony, impromptu activity.  You can go out to dinner first, which everyone agrees is a satisfying shared activity. If the dinner goes well, you can offer to take your date to the movies.  If he/she says no, that’s okay.  But if he/she says yes, then it is on.

Even if dinner proves to both parties that the date was a mistake, a movie is a nice way to not have to talk to the other person for the rest of the night.  You can live vicariously, for about two hours, through the lives of the more attractive characters on the screen.  Go pretend that it’s you extracting information from another man’s dream, or get mistaken for a criminal while on a nice dinner date with your wife. Ahem, Tina Fey.

However, if dinner goes well, then the movie experience will prove even better.  Once you’re at the theatre sitting in your comfy, reclining chairs with optional armrests, it feels great.  The air conditioning is usually on high.  You’ve already (hopefully) shared fulfilling conversations, so now you can relax.  It’s okay to sit back and unwind.  You don’t have to talk for the entire date; sitting while not talking will probably comprise a good portion of your marriage in the future, anyway.  Might as well sit back and enjoy yourself.

My friend Miriam* called me for advice the other day. She met a guy JDate but things haven’t exactly gone smoothly. He sent her the initial email on JDate which was good and after exchanging a few e-mails he asked her, still via JDate e-mail, to meet him for a glass of wine. She responded with her phone number. His response: his phone number. Obviously, they didn’t meet because someone had to make the first phone call, right? After a few more e-mails throughout the weekend he again asked her to meet, this time for gelato. She responded with her phone number. His response: a text. The non-existent relationship went from confusing to annoying.

She told him she wasn’t a text person, but he told her he wasn’t a phone person. It was enough to make a girl give up and Miriam was just about to throw in the towel. I advised her to stop playing his game and not respond to his texts. It worked. He finally called the next day to ask her out. Finally, they met but all that effort was wasted as it wasn’t meant to be. I doubt this guy is going to find his Beshert if he continues to be difficult and communicate with women in this bizarre way.

*all names have been changed

Julie* recently went on a JDate with Brian, a good looking lawyer who recently moved to town. Unfortunately, the report was not good. Yes, Brian was handsome and smart, but no, he’s not an avid conversationalist. This guy didn’t know the meaning of biting his tongue or having restraint — he was an open book but Julie had barely read the back cover. The more he told Julie about himself, the less interested she became.

Brian proceeded to tell Julie all about his entire life over the course of one drink and one hour: his father’s six ex-wives; the medicines Brian takes for OCD and ADHD; his dyslexia; his skin rashes; his likes and dislikes; and finally – the kicker – his ex-girlfriend. None of the items are particularly funny when heard separately, but when taken altogether it was a dark comedy that had come to life.

Maybe Brian was trying to put all his cards on the table and let Julie know exactly what she’s getting into, but his technique needs some major help. Of the above list, the only topic that should be discussed during a first date is your likes and dislikes. JDate makes you feel like you know someone better than you really do before you even meet, but remember that the person sitting across from you is still a stranger. The prescriptions in your medicine cabinet are not something you would discuss with the person sitting next to you in the doctor’s waiting room, so why share it with a girl you’re trying to impress?

One of the reasons I suggest meeting your JDate matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. You have the topics right in front of you when you look at their profiles, so use it to your advantage and keep to the typical first date conversation topics within those guidelines: why did you choose to go to [college]? Where did you grow up? How did you get started in your career? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business right now. On the first few dates, regale your date with funny, positive and interesting stories about yourself and leave the deeper, sad and bewildering stories for later on in the relationship. Hopefully you will be charming enough with the former to leave plenty of time for the latter.

*all names have been changed

I am trying to get better at determining when it’s a good time to transition from an online conversation, either via email or Instant Message, to an actual face to face first date, or when I am better off just ending things because neither of us really seems that interested.  As I’ve mentioned in previous blogs I am not someone who operates under the same pretenses and patterns with every person that I meet online.  Therefore, it is important that I read the situation correctly and trust my instincts so that I don’t waste my time talking to a bunch of women with limited potential for actually ever going out on an enjoyable date.

While figuring this out isn’t rocket science I do believe that there is a fair amount of calculations that go into determining what is the right course of action in a given situation. First off, let me reiterate my feeling that you can’t treat every person and situation the same, and those who have a template for how they approach and communicate with people in my opinion are making a big mistake. You can’t lump everyone you meet, whether it’s online, at a bar, or at work, into one group and interact with them all in the exact same way. While I do understand that some people like to ask a few of the same initial questions of those they are getting to know, that is hardly the same as waiting for a certain amount of emails  to transpire before asking someone out for coffee, no matter what vibe the other person is giving you.

You have to feel people out; pay attention to the underlying tone in their responses in order to determine if they are becoming more comfortable sharing information with you, or whether they seem to be uninterested. One of the questions I always try to ask myself is whether or not I feel like the other person is pushing the conversation forward as much as I am. Are they asking me questions that show they’re truly interested in me, or are they just answering my questions and repeating them back to me?  If that is the case then perhaps I should just leave well enough alone since I’m not getting very much out of the correspondence.

During every online conversation there are signals that indicate if things are going well and if it’s the right time to meet, or if it’s not. Often times, especially when we haven’t had any good conversations in a while, we try to force things along and end up either turning the other person off or going out on a first date that we never should have gone on. So keep an open mind when talking with people, trust your instincts when gauging their responses and figuring out their level of interest in you, because there are a lot of fish in the online sea so why waste your time trying to force things to work with the wrong ones.

Another broken rule that can be given a “pass” is when a guy calls to ask you out for the weekend after Wednesday. On one hand a man may need to know you require more advanced warning because you are a busy and popular gal, but if he’s calling you on a Thursday for Saturday and you have nothing to do and on top of that you actually like the guy, than why not accept the date? This “pass” is perfect for giving out (theoretically given out, please don’t actually tell him you’re giving him a “pass” or make a book of coupons) when you met the man within the same week or when you know he’s just returning from a work trip or when you had your first date a few days prior and you really enjoyed yourself and want to keep the momentum going.

A “pass” should not be given out in extreme circumstances. Sometimes you need to set a bar for yourself on how you wish to be treated and not let anyone manipulate those standards, no matter how charming he may be. Like when you emailed a JDate your phone number and he ignored it completely and continued to email you. A “pass” should not be given out when you feel disappointed or hurt because you don’t want to set a precedent that this type of behavior is okay.

Silly rules for dating have been created by people who used the tactics once – and coincidentally succeeded – rules are made to be broken for just this reason… they are silly! If you want to give a guy a break for waiting three days to call you instead of two, then do so. Who knows, he may be the one and had you not given him some leeway you would never have known that.

Dear Tamar,

I have been on JDate for a few months. More than 100 men have viewed my profile. I am communicative and don’t hesitate to reach out. I don’t usually have self confidence issues, am optimistic and funny but no one responds to me. Many of those men seemed like serious, interesting people who I’d love to meet just for coffee. I do not mind being on my own, but I desire companionship and connections with other people. My father suggested it’s because I am healing from a spinal problem. I have so much to offer the right person, but I won’t be dishonest. Could people possibly be rejecting me because I can’t do cartwheels right now? The lack of response is disheartening, but also baffling. I tell myself I am only looking for one, but it doesn’t change the fact that no one responds to me. Any advice?

Dear What’s TMI?

I give you credit for making such an effort while recovering from a spinal injury. That said, I don’t think mentioning that injury is necessary in an introductory email and especially not in your profile — this includes not having photos showing your injury. You’re not lying; this information is simply none of their business at this point. To put it blunt — these guys are basically strangers right now. A disability, a divorce, or depression, or anything that could be seen as negative or as “baggage,” is TMI — too much information. My advice would be to not mention your injury and recovery until you are making plans to meet. The first date will probably take place at the typical bar, restaurant or coffee shop, so simply mention you’ll be arriving in a brace or using a walker or what-have-you and briefly explain why and offer to tell the whole story on the date. Do not mention your injury before then. Any emails you send to men on JDate should be casual, upbeat, and short and sweet. Mentioning this and explaining your recovery from a spinal injury is anything but those three things and it unfortunately doesn’t surprise me that you haven’t received a response. I bet with your new approach, you will! Good luck on your recovery and on finding love!

It doesn’t feel good when someone doesn’t respond to your email, accept your invitation to chat via Instant Messenger, or call you after a first or second date, however, these are inevitable parts of not only the online dating experience but also dating in general. Over time, and through experience, we all might get better at letting these disappointments roll off our backs; however it is human nature to feel a sense of rejection in each of these situations. This feeling is the price we pay for putting ourselves out there, and giving ourselves a chance to meet someone special.

The alternative to this proactive approach is that we sit back and wait for someone to find us and sweep us off our feet, but is that really a likely scenario? Even if a more passive, “wait and see” approach was a viable option, does that really guarantee that we aren’t going to incur any negative feelings from the dating process just because the other person found us and put themselves out there first? With the ball in our court we still stand the chance that our response won’t be perceived well, either via email or on a first date, and that will abruptly end the interaction.

Furthermore, waiting around for people to contact you limits the number of people you meet, and leaves you at the mercy of those who randomly stumble across your profile. This is in stark contrast to someone who puts themselves out there by continuously looking for people that attract their interest, and then attempting to begin a correspondence with them, who in the process might run more of a risk of getting hurt or disappointed. But they also have a much higher chance of meeting a lot of interesting people and having an abundance of new experiences in the process.

Maybe my more proactive approach to dating isn’t the norm.  I know that guys are the ones who are typically supposed to take the lead in these types of situations, but I say regardless of your age, sex or past dating experiences that we all owe it to ourselves to embrace dating as a fun and unique challenge where each experience is different and an opportunity to develop into something great. So please don’t sit back and wait for the perfect situation to fall into your lap when you can take control by going out and finding it for yourself. Sure, along the way there will be some disappointments and agonizing moments, but there will also be ones of pure joy and satisfaction, which in my opinion makes it all worthwhile many times over.