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 100hookup 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 100hookup 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 100hookup 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.

Dear Tamar,

I am completely baffled. I have had a series of dates recently, which I have considered successful. Good conversations and nice dinners lasting more than two hours.  I am always taken to very nice restaurants and the men seem thoroughly engaged. I get thanked for actually looking like my photo and receive compliments during the meal. Sometimes there is even a substantial kiss goodnight…then I hear nothing further. The process is becoming very tiresome because I can’t figure out where I go wrong.

I know the answer is to keep dating and the right one will come along, but I don’t understand the lack of real interest among these guys. It seems like a sport that men just like to take women out. Personally, I don’t get it. These meals are $100+ because most seem to order a bottle of wine. Why blow that much money? It just doesn’t make sense.

Dear WTF?,

Ugh, I totally remember being in your shoes and it was beyond frustrating! I can totally empathize. Unfortunately, as you said, the obvious answer is to keep dating and wait until your beshert comes along. But there are some other things you can do in the meantime… try to use this opportunity for some introspection. Look at yourself from an outsider’s perspective: What kind of vibes are you giving off? How much information are you sharing about yourself? Do you really see yourself with the men you’re on dates with? By answering those questions (and any others you think of) I believe you will find yourself having more productive and successful dates. Don’t give up. Oh, and if the guys want to drop that kind of cash on you and then not call you — it’s their loss, literally! Good luck!

Dear Tamar,

I am so incredibly puzzled. I have gone on numerous dates that all seem really great. They’d last an average of 2-3 hours for dinner. My photos are completely accurate and updated.  In fact, I am often thanked for being so honest. I am 48 and look much younger (and awkward to say about myself, but I am considered very attractive). I have teens and am dating men around the same age as me. I have been completely puzzled because I am not being called for second dates by those I would like to have a second date with. One recently texted 30 minutes after the date to say he had a great time…and then no follow up. I am really confused and feel like shelving dating.

Dear Ready to Give Up,

Don’t shelf dating just yet. I look at this from a “so far, so good” perspective: you obviously have good photos (and look like them!), you have a lot of life left to live and the men are spending a pretty big chunk of their time with you. If you remember dating the first time around, you’ll recall it wasn’t easy then either. And now you’re bringing age, experience, kids, and all the pluses and minuses that come with that to the table — and probably so are the men you’re dating. So what’s the problem? Why aren’t you getting 2nd dates?

I think what you have to look at are the conversations you’re having on the dates: are you talking about yourself and asking questions about your date? Or, are you commiserating about your past relationships, the stress of having teenagers and so forth? Although these topics may seem like bonding conversations and you may think that by putting all your cards on the table the man will know what he’s getting into, these topics also have negative connotations and may not leave a man thinking he’s had a great time.  Instead, he may think he’s left a therapy session.

Once you meet someone you like you’ll each have plenty of time to discuss your past, but right now you should be talking about upbeat, positive subjects. What interests and hobbies do you have in common? Play hookup Geography (but don’t talk badly about anyone, that’s bad karma). Talk about what you’re both looking for in the future. I believe if you stick to these topics on 1st dates you will start landing some 2nd dates. Just don’t give up, it will happen! Good luck!

Aah the quintessential first date exchange of resume and family history….how scintillating… Yes, it may give you some info, but really does it??  You don’t choose the family you’re born into and the reality is sometimes siblings are polar opposites.  Not ideal, but not so uncommon.  Then the resume… I’m a trained attorney who has been on the recovery path ever since–and I applaud those who don’t stick to the golden handcuffs through societal pressure norms and take risks and make changes.  Whatever floats your boat and makes you happy when you get out of bed.

Yet, once in awhile you break the rules of what not to do on a first date and you simply connect.  There is no guarantee that will predict the success of a relationship any better than a slow burning candle courtship, but it sure is genuine when you throw caution to the wind (not to mention fun), talk about real stuff and enjoy custard.

One of the reasons I suggest meeting your 100hookup matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. Since you’ve divulged more information than you would typically about each other in your profiles, too much emailing and phone calling will only make your actual first date feel much more serious than it actually is. Stay within the parameters of the questions asked in the 100hookup profile so that your first date doesn’t feel (or proceed) more like a 3rd date — since it isn’t.

Instead, ask for details about the fill-in the blank questions and multiple choice questions — Why did you choose the university and the major you did? Why did you pick the career path you did and is it what you wanted to be when you were growing up? Where did you grow up and how did you pick where to settle down? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business — at least not yet. On the first few dates, regale your date with the 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 able to charm enough with the former to leave plenty of time for the latter.

Going on 100hookups can be fun and entertaining (or dull and torturous, but this column is dedicated to the former!), so how do you turn a 100hookup into something more?

After the first date, a man who is interested should call the woman within two days, if not the next day. You can even send a text later that night or the next morning saying how good of a time you had – but don’t get in the habit of texting at this stage! (My anti-texting rampage is yet to come.)

When you call after the first date, make immediate plans for a second date, preferably within the next week. You don’t want to lose momentum. You’re getting to know each other, enjoying each other’s company and building on the chemistry. If you know you have a business trip, try to squeeze another date in before you leave or make plans in advance for when you return. Whomever is out of town should try to call once or twice while away but otherwise, you shouldn’t be spending too much time on the phone at this point, just let the other person know you are definitely interested and not blowing him or her off.

When you plan the second, third and fourth dates they should continue to be casual, comfortable and full of quality-time. That means no friends, not too much alcohol and no weddings of your third-cousin-twice-removed. Get to know each other sober and alone before introducing each other to your crazy fraternity brother or even crazier Great Aunt. Daytime dates are also a good option. Go for a walk in a park with a picnic basket to eat while you watch the sunset. Go to the zoo, the fair or an amusement park, or even miniature golfing or go-cart racing. Find a fun activity that will allow your inner child to come out, where you can laugh, and engage in some physical contact that’s not overtly sexual.

I remember when I was on 100hookup and meeting someone for the first time… it was so daunting! Would he look like his photos? Would we recognize each other? Would it be one of those awkward introductions where someone sticks out a hand to shake while the other goes in for a hug? I have a few solutions for these very problems!

Check out your 100hookup’s profile one last time before the date. Look at all the pictures offered since you never know which one he or she is actually going to look like. Then, as you’re pulling up to the restaurant, coffee shop or bar (I’ll get to that later) call your date and ask him or her to meet you outside. That way you don’t have to scan the back of people’s heads at the bar trying to figure out which is your date without looking like a deranged stalker. Once you see each other — and trust me, you will recognize each other when no one else is around! — you should both go in for a friendly hug. Afterall, you know enough about each other at this point that its more like a 2nd date, right?

Next:  Making Small Talk