Dear Tamar,

Per your advice, I’ve been poly-dating for quite some time (although I didn’t have a name for it before, lol, so thanks for that) but I’m in a jam – I really like two of the guys I’m dating and I can’t decide which to break it off with. Not to say it’s totally up to me, but I’m pretty sure they both feel strongly towards me and I need to make a move now before it becomes more difficult. Have you ever been in this predicament?

Dear Poly-Dater,

Lucky for you (and unfortunately for me), I was in your situation before. I had met two guys when I was in the midst of a poly-dating phase of my life and was stuck. Surely these guys knew I was holding back as I was still only seeing them each twice a week, and although I was naturally flirtatious, I hadn’t let the physical chemistry get the best of me.

Both were great guys, but there was something about one of them which I couldn’t put my finger on and couldn’t ignore. I ultimately “chose” him and broke things off with the other guy. Things became really serious once I let my guard down and truly became available. Of course, after a few months the relationship ended, but for that time I had made the right choice.

It’s a gut feeling. Neither ended up being right for me, but of the two at that time one was more right than the other. You have to trust your instinct. The best way to do so, if you’re confused, is to try and imagine yourself with each of the men down the road – can you picture having a conversation with each guy in a month, a year, ten years? Can you imagine yourself living with each guy, marrying each guy, parenting with each guy? That may sound extreme, but if you can’t envision yourself making a home with a man, then why bother?

That said, keep this process and your poly-dating past to yourself. The guys don’t want to hear that there are other men in your life even if they’re dating other women. And they for sure don’t want to know that you can’t choose between them and another man.

My girlfriend Esther* called me last night with a new dating debacle. She met this guy she knows from the community on 100hookup. His name is Yoni and once they started instant messaging each other, conversation flowed, she laughed, she was interested and it seemed 100% mutual. They went out and the date went really well, too. There was chemistry and they had a lot in common and they wanted to make plans to see each other again. Then the problem reared its ugly head.

Esther started telling some girlfriends that she had met this great guy, a guy she knew from the community but a guy she admittedly probably wouldn’t have given a chance to had he approached her at a local hookup event. Once she said it was Yoni she started to hear rumors about more and more friends and acquaintances whom had all dated him. Turns out the guy is a serial dater.

Since I know Yoni, too, I was able to give Esther some advice. Yoni really wants to get married (although not exactly in a stinking-of-desperation kind of way) and is willing to turn over every rock to find his Beshert, I don’t see a problem with that but it’s tough to hear he has dated every relatively attractive woman who is active in the community. Some were just one or two dates, others were long term relationships. None of the women had anything bad to say about Yoni, just that “it” wasn’t there. When Yoni runs into his exes at events they greet him cordially with a warm hug and kiss on the cheek. There is no animosity. But there’s also no concrete reason any of them stopped dating. There’s just something you can’t quite put your finger on.

Instinctually, I didn’t think Yoni was right for Esther, but I thought he would be good dating practice so I softened the edges for her. I told her that she shouldn’t have a problem with someone who has dated everyone possible, it just means they are looking for the same thing as her. As long as her friends who dated the guy give her their blessing and warn her if there’s anything worth knowing, I say all he’s free game. Esther had realistic reasons to be concerned, but she had already been on a date with him and enjoyed herself, so why should she be punished because other people didn’t have as successful as dates? I told her that I would be more concerned if she didn’t know one person whom he had dated. Yoni was obviously committed to finding a hookup woman, and that’s exactly the type of guy Esther was looking for.

Dear Tamar,

I am new to dating.  I have been divorced for nine months.  How do I tactfully start dating two or three gentleman? Dating for me means going out to do activities both persons are interested in. How do I date, on this simple premise, without feeling awkward?

Dear Poly-Dating,

Welcome back to dating… I guess. It’s easy and can be fun to date more than one person at a time particularly when you’ve recently returned to dating. Think of it as practice or rebounding or what-have-you, but until you get your training wheels off it would be smart of you to date more than one person at a time. As for how to do it tactfully well, simply put, it’s no one else’s business. Sleeping with more than one person at a time is a different story, but just dating isn’t harming anyone; in fact, it’s healthy. Definitely stick to activities you are both interested in as that will create a common bond but be careful if you repeat the same activity with another date because you may get mixed up and forget whom you did what with and when. Now is the time to enjoy yourself and if you happen to find someone you really like and the feeling is mutual then you will simply tell the others exactly that. Have fun!

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 100hookup 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 100hookup 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 hookup gals at a bar then 100hookup wouldn’t exist, but the fact is that you can’t; no one can, which is why 100hookup 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!