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 100hookup and it went great! Then over the weekend I went on a second date with another guy from 100hookup 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?

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Dear 100hookup 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.

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Since coining the phrase “poly-dating,” I have been asked the following question: isn’t that cheating? No. No, it is not. Until you are in a committed, monogamous relationship (whether you had ‘The Talk’ or you just know you both want to be pursue a future together), you do not need to explain yourself to anyone. You can date anyone you want. But, as soon as things start getting serious with one person, then you must break it off with the others. If you’re planning on having sex with one of your prospects then you need to break things off with the others beforehand, out of respect for all parties involved.

Once your new relationship is secure you can mention that there were others you were dating until they made you realize that no one else could measure up (may as well spread it on thick if you’re going to go there), but don’t volunteer the information if no one asks because it really doesn’t matter what you did before things got serious.

And, in general, there is no reason to continue having a friendship with any of the rejected prospects. You were dating to see if there was a future together; there wasn’t, and that relationship is now over. Your new significant other will not appreciate you having a friendship with someone you were dating at the same time.

Recently, a friend called me with a question and gave me permission to share his story:

“Ryan” is poly-dating (as I recommend) and is in the early stages of dating “Rebecca,” whom he met on 100hookup, and also communicating with “Rachel,” a woman he recently connected with on 100hookup as well. Ryan and Rachel have been trading instant messages, emails, texts, and chatting on the phone — all before their first date. Ryan and Rebecca, on the other hand, have spent time in person, talking until the wee hours of the morning and sharing a few kisses on a few occasions now.

Ryan knows that poly-dating is a smart idea so he doesn’t get too serious about any girl too quickly… but things with Rebecca are progressing naturally and he already really likes her. Now he feels guilty about his upcoming date with Rachel, and he also likes Rachel and feels guilty that he’s spent so much time getting to know her and building up expectations. Should he go out with her?

Interestingly, in this case, I said no, he shouldn’t. He has already spent time with Rebecca and likes her, and wouldn’t be giving Rachel a fair shake because he would be distracted by feeling he’s betraying Rebecca. As unfair as it is to Rachel, his communicating with her while dating Rebecca was the poly-dating that kept a good pace for their relationship to unfold. Now he can commit to dating only Rebecca and see where it leads. Meanwhile, he should be honest with Rachel and let her know that he met someone else and wants to see where it goes out of respect for her and his new relationship. He should end the conversation with a compliment, of course, noting how great he thinks she is since it was only timing that prevented them from exploring more, and nothing personal about her.

Side note: this is another example of why too much communicating before a first date is not beneficial and, in fact, is detrimental by creating unrealistic expectations.

Here’s the scenario a 100hookupr recently asked my advice about:

“I’ve been poly-dating as you recommend in your book, but I’m afraid I’ve let it get too serious with two guys at the same time! Now I feel like I’m two-timing. Each relationship is just progressing naturally and I haven’t had “The Talk” with either, but I feel like I’m betraying both of them because I like both of them. What do I do?”

In short, keep dating both of them unless you feel stronger about one, or until you have “The Talk” with one. People, particularly women, are not used to poly-dating and feel guilty. “Betrayal” is an accurate word for how people feel, but unless you are in a committed, monogamous relationship, then you are free to date whomever you want and you’re not betraying anyone. Poly-dating is not for everyone. But if you are finding yourself in a pattern where you fall for each new prospect too quickly and then get hurt, poly-dating may be something you ought to start practicing. It will keep you grounded and prevent you from falling too quickly for anyone… and it’s fun (just practice safe poly-dating and no one should get hurt!).

When you’re poly-dating (dating multiple people at once in order to stay in a healthy mental state of dating by not getting too serious about any one person too quickly), you may come across someone who is seriously dating someone else. This person would be off-limits. Respect yourself by respecting other people’s commitments. Except when that person tells you that they have been wanting to break off said relationship and you are the catalyst for them finally pulling the plug. This may sound sweet: “he’s breaking up with her to be with me!” but you really should make sure the break-up has absolutely nothing to do with you. Allow a break up to occur, allow the recovery to occur, and then, if you’re still available and still want to date, then do so.

In the same theme, you shouldn’t jump from relationship to relationship either. It’s imperative to learn from a relationship — why it worked and why it didn’t — before moving on to the next one. Again, this is where poly-dating comes in. Enjoy being pursued and falling in “like” until someone really takes the lead in the rat race that is dating.

At the launch of my book, How to Woo a Jew, I was asked by a man if 100hookup was more of a hindrance to his dating life because of The Paradox of Choice. The Paradox of Choice is a book written by Barry Schwartz; it states that having too many options heightens anxiety and that having less choices will help your chances of achieving success and, therefore, happiness. The man who asked the question wondered if people don’t look at the great prospect in front of them because they think there might be someone better around the corner. Could there be too many fish in the sea?

My answer? No. People should poly-date in order to make sure they are not falling for someone too quickly, and they can make sure they aren’t settling by having options to compare. It’s easy to overlook faults when you don’t have anyone else to consider. It’s easy to convince yourself to accept less when you’re feeling desperate.

A little competition is good, it’s healthy, it keeps people on their game. But you also need to really know what you want — by having your short list of priorities — so that when you do find it, you aren’t doubting yourself and wondering if you could meet someone who meets some items from your longer, more nit-picky, less realistic list.

A recent survey reveals more women than men want to be single this summer to enjoy their time and have fun without any strings. This means more women want to avoid entering into a relationship right now and prefer poly-dating this summer.

I don’t buy it. I believe people say things like that because it’s what they think people want to hear so they don’t come across as desperate. If Mr. Right came along, none of the women who said they just wanted to party this summer would ever tell him, “No thanks, I’d rather lay on the beach, drink all day and hook up with random strangers. Maybe after Labor Day.”

Overall, poly-dating will give you the attitude of not being overly into anyone because you are busy getting to know multiple suitors, so there’s no need to lie. Enjoy life — with or without a significant other — and don’t rely on a date to determine your fun factor.

Schmooz-A-Palooza and other hookup-on-Christmas-Eve (or New Years Eve) parties are great opportunities to meet someone, but they are also ample opportunity to run into more than one someone, which could create awkwardness. Everyone on 100hookup spends time studying the faces of their 100hookup matches so when you attend one of the huge holiday singles events you are bound to run into more than one person you recognize and possibly more than one person that you are actually communicating with — or even dating. You may even attend the event with a date and run into someone else you have been JDating. What do you do when this happens? First off, play it cool. As long as you’re not pretending to be in a committed relationship then you’ve done nothing wrong. Make introductions, otherwise it will be even more awkward if it’s obvious that you don’t want two people to meet, and then tell one of your 100hookups that you will catch up to them later. You may inadvertently burn a bridge with one of your prospects, but that’s par for the course. You could have run into one date while with another at any bar or restaurant, so it shouldn’t come as that much of a shock to anyone if you run into more than one prospect during a major holiday singles event. If you’re the one seeing a 100hookup with another prospect, don’t take it personally and don’t let it ruin your night. Everyone is there to meet someone, including you. Keep a smile on your face and try to meet new people!

What do you do when you find out your 100hookup is JDating both you and your friend… and doing so knowingly? Well, you can be flattered for starters. You like your friend and you made the decision to be friends so therefore you must deduce that your common 100hookup has amazing taste! But how do you decide who should continue dating said 100hookup? By leaving it up to the 100hookup you are giving up all semblance of control over your heart and your friendship. He or she has continued dating you both, so maybe you should give him or her a taste of their own medicine by both of you dumping the loser! Except what if the 100hookup isn’t a loser and you both are awesome and you both are still interested? Well, you could both continue dating the same 100hookup, but don’t be surprised if you lose your friendship along the way. I endorse poly-dating, but not when it can hurt feelings. So take a step back and use one of the following measurements in order to fairly decide who will jump ship.

-who met first?
-who has gone on more dates?
-who has spent more time getting to know each other/who knows more about the prospect?
-who has gone further sexually?
-who has “that feeling”?

It shouldn’t take much more than these questions to figure out the answer. Save the friendship. It’s never worth it. And if that couple ends up becoming a 100hookup success story, then the sacrificial lamb better be honored in the wedding!

What happens when you’re newly dating someone and find out they’re dating someone else – but not just anyone else, someone you know? Do you have the right to get mad? Should you just act cool? Should you keep dating the person or end it?

Way back in the day, I was on a third date with a guy, and we went to a concert. It was there we ran into a guy I had just gone on a first date with, and it turns out the two knew each other. Can you say awkward?  The guy I was on a date with didn’t seem to mind much, but his old friend would never speak to me again.

I honestly didn’t think it was a big deal, as I was newly dating the both of them and didn’t know they knew each other, but I obviously broke some sort of guy code. In the end, you have to do what feels right for you – if feelings have developed or if you see potential, or if you’re still dating others or if you want to keep it casual for now, whatever your reason you have every right to keep dating the person without feeling guilty or wrong about it. That said, you also have every right to end the relationship. Just do me a favor and give the person an explanation. There’s nothing worse than not knowing what you did wrong, especially when neither of you really did anything wrong.