When Is The Right Time To Choose Between Two Amazing Men?

I am in a quandary and I am hoping you can help. Last month, I wrote to two men that I was very interested in. The good news is that both of them wrote me back and I have been seeing both for the past 2-3 weeks. Things have been going well, and I give a lot of credit to what I have learned from your book, emails and this site. However, this is not something I have ever done before and I am having a hard time with the idea of juggling.

The problem is that I really like both of them and they both seem to be really amazing guys. They follow up, they text, we talk, make plans…it’s all good. I am lucky. On the other hand, I don’t know how to manage this. I know I need to make a decision before things go too far (becoming too physical), but how do I know when? I am trying not to let things move too fast physically or emotionally, but they both seem very interested and I just don’t know what to do.

Making a decision about a guy is no different than any other decision. You weigh your pros and cons, you do your cost-benefit analysis, you use a little logic and a little emotion, and then make a largely arbitrary choice without knowing if you’re right.

Many people may not see this as being a true problem. But I don’t know how much to say to these men, or not say because it’s so early in the relationship. They seem to be feeling pretty strongly so I feel some pressure to figure this out.

I searched the blog to see if you’ve addressed this before but haven’t found quite the same thing. Any help you can provide would be so appreciated.

Thank you,
Maggie

High quality problems, indeed.

So, Maggie, you’re seeing two great guys for 2-3 weeks. You didn’t give me any identifying information that would allow me to recommend one man or the other, so all I’m left with is the general idea of dating multiple men simultaneously. The good news: because of the broad scope of the question, every reader who is interested in deciding between two men can use this advice. The bad news: without more specific details, I’m not sure you can.

Regardless, I’m going to do what I always do in these situations: insert myself in the middle and riff a little bit.

1. Making a decision about a guy is no different than any other decision. You weigh your pros and cons, you do your cost-benefit analysis, you use a little logic and a little emotion, and then make a largely arbitrary choice without knowing if you’re right.

I recall one time that I was dating two women simultaneously for about a month. Both were cute, smart, cool, late 20’s, Jewish, and interested in me. And while I was hooking up with (not sleeping with) both of them, something didn’t feel right. I couldn’t act silly around them. I couldn’t let down my guard around them. I didn’t LOVE being around them. My ambivalence was a feeling, more than a logical choice. Which is why I kept looking around on JDate for that entire month that I was seeing both of them. One woman even called me on it — “How dare you get online after our great date?” but I didn’t flinch. It was my right to look for other women if I didn’t feel I could commit to her. Just as it’s her right to keep her options open until she finds a boyfriend-worthy man.

As it turns out, I met a third woman, who was so incredible that I immediately emailed the other two, broke things off, and took my profile down to commit. Naturally, it took the third woman about two weeks to feel comfortable committing to me, but she eventually did.

This is a somewhat complicated (but typical) example of how dating works. It’s every man for himself. And neither party is under any obligation until both parties agree to commit to each other.

Which brings me to a very important point:

2. Your choice is not binary, nor is it permanent. Yes, you’re dating two men, but that doesn’t mean that these are the only two men on the planet.

Let’s say Bachelor #1 turns out to be a great guy…who admits after a month that he never wants to get married or have kids. You do.This conversation is over. You agree to be exclusive with Bachelor #2.

Let’s say Bachelor #2 turns out to be a great guy…who admits after two months that although he was excited about you, he’s on the rebound, not emotionally over his ex-girlfriend and is not fit to be your partner at this point in time.
What does that say about you, men, or dating?

Yes, you’re dating two men, but that doesn’t mean that these are the only two men on the planet.

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Nothing! All it tells us is that…

3. Time reveals all.

You may not know the front-runner for the open position of “boyfriend”, but since you’re the CEO of Maggie, Inc, you’re going to take your sweet time to see how the interns perform in a limited capacity. The faster they follow up, the more work they choose to take on, the quality of their performance — all will start to differentiate these two men to make your decision a lot easier. You’ve never heard of a woman standing on the altar with two men, have you? Exactly.

Everyone figures this out, eventually. And finally…

4. Physical intimacy is a personal decision.

For me, I decided back in 2004 that I wouldn’t sleep with anyone who wasn’t a girlfriend. I stuck with that and avoided breaking a lot of hearts. In general, I think this is the best policy, because it’s a clear dividing line that any man can understand.

“I only sleep with boyfriends, and until we figure out if an exclusive relationship is the right course of action for both of us, we’re gonna have to just stick with some incredible foreplay!”

Only you can determine whether you can have sex with two guys simultaneously without a commitment to either of them. But I wouldn’t recommend it. Either you will get attached or THEY will get attached — and since you haven’t figured out your feelings yet, I would think that attachment is something you’d want to avoid.

I predict that by the time you read this, Maggie, everything will have sorted itself out. So please come back and let us know if I retroactively steered you in the right direction, okay?