Ask the Guy’s Guy: I Want to Date More Than One Person, Should I?

By Robert Manni

Question from Dani P: “So I’ve only been on a few dates with two separate girls. They are both cool and fun to hang out with. I told one girl that I was seeing someone else (we’ve only been on a couple of dates) and she said I have to choose. I don’t know if I should choose between them. If I don’t I won’t get to see what things could have become though.  I came out of a long relationship a year ago and don’t think I’m ready to be serious, but I really like this girl. What should I do?”

What are you really looking for in dating two or more people?

Hi Dani, 

It seems like you want to have your cake and eat it too, and fundamentally, there’s nothing wrong with that. After all, life is about finding joy and living your passion. So dating, which usually means seeing more than one person, is fine. However, life is determined by the choices we make, and it seems like it’s time to make some choices about what you want and who you want to spend your time with.

Related Link: Ask The Guy’s Guy: What Do I Do If I Have Trouble Opening Up To My Significant Other

You are single and free and that’s all good, but you need to decide what you want out of dating. From my own experience, I’ve met too many people who did not know what they wanted out of dating, and to a person, these singles always ran into problems just like yours. For every single person who is unsure what they want there is another who knows precisely who and want they want. In your case, it sounds like the woman who does not want you dating others either wants you all to herself because she really digs you, or she is pulling a power play. You’ll have to do some work to find out which is true.

I suggest you take a step back and ask yourself what you want now that you’re single again. It sounds like you want to play the field for a while. If that’s true, then play the field and don’t allow anyone to control what you do, especially when you’re doing what say you want to do. If it feels too early to get serious with this person, tell her you dig her, but that you just got back into the single life and would like to take things slowly for now. If she does not accept that, this may be a sign of her future behavior and your freedom. Take note of how she reacts and her response. 

On the other hand, you state that you like her and would like to see her again. Cool. Then tell her you like her and would like to see her again, but make sure she also knows that you are not ready to settle into a committed relationship at this time. If she’s understanding and she really digs you, she will respect your feelings and behave accordingly.

Related Link: Ask The Guy’s Guy: If He Isn’t Ready To Date, What Should I Do?

The bottom line is you need to decide for yourself what you want out of dating right now and then be honest and clear about how you feel with potential partners if the subject surfaces. After all, you are the priority, and if you are not sure of what you want or how you feel, it could send out indecisive energy that can lead to similar situations.

The good news is that you are happily single and free, you’re dating, and people want to date you. You’re in a better situation than many of your contemporaries and all you need to do is follow your heart, decide what works for you, and be crystal clear with your potential partners about where you stand if the subject comes up.

Hope this helps,

Guy’s Guy