Wednesday, October 26, 2011

Dating Multilple People at the Same Time: Some Notes

After engaging in several discussions, both online and off, I have come to a more nuanced position on the whole "dating multiple people at the same time" issue. Actually, it would be more accurate to say that what I have been doing in my own life became clearer, and I realized I was presenting too simplistic of a picture in comments I was making on other blogs.

So, here's what I think: you need a different approach based upon how strongly you are interested in someone you're dating.

This may seem obvious to readers, but I'm realizing that many folks seem to employ the same strategy regardless of what's happening. If they're scared of falling in love too quickly and getting "burned," they always keep their options open. Others, who maybe are more like me, tend to pull most or all of their energy into a single person, even if they feel lukewarm about the dates with that person.

So, what I want to advocate for is inline with what I have already spoken a lot about on this blog: learning to pay closer attention, and make decisions based on what you are actually experiencing.

Here are a few examples from my own dating life to help illustrate. I went on 4 dates with a woman last winter I would call "nice" and "interesting." The time we spent together was comfortable, and we seemed to get along fairly well. But other things were lacking. Four dates and almost zero touching. Our conversations were more intellectual and less heart-based. And every time a date would end, it wasn't really clear if we'd even see each other again. Overall, I really wasn’t sure what to think. And I don’t think she was either. You could say the whole thing was "lukewarm."

In situations where you feel lukewarm like this, it makes sense to keep the door open for awhile. While I didn’t go on dates with anyone else during that month I was dating the woman in the story above, if someone interesting had shown up, I probably would have considered doing so. And certainly, if I had been talking to someone else during that time already, I would have continued to do so.

On the other hand, there was the woman I dated for about 7 weeks this spring. From the beginning, I really liked her who approach to relationships. We actually talked about what we wanted in detail on our first date, and continued to do so throughout the whole time we spent together. She really had her shit together, and had reflected a lot on what it meant to be a healthy person partnering with another healthy person. We also had fun together, and got along well. Although I wasn't sure about the level of attraction between us, I definitely felt more than lukewarm about her. So, I decided to hide my online profiles and focus on dating her following the third date.

Even though, in the end, neither of us felt there was enough between us to build a long term relationship on, it was totally worth it to have focused on being with her alone and not worrying about "other possibilities." I really got to know her as a person, as opposed to solely "a potential partner," something I think happens frequently when people are juggling multiple options for weeks and months on end. You're too busy looking for what you want or don't want, and end up missing the person in front of you.

Overall, if you feel a good connection with someone, and start to wonder if they might be a good long term partner, it just makes sense to me to put your focus on being with them, fully and completely. How else can you really get to know someone?

Some people argue that most of the time, things don't work out. Which is true. Most of the time, things don't work out.

However, I disagree with the idea that you better "always keep your options open" because things might not work out. It just feels like a set up for failure. A constant hedging of bets.

And if you are someone who is worried about falling in love too soon, and getting "burned" after a few months, you might want to take a look at yourself. Do you have healthy personal boundaries? Are you in love with the idea or feeling of being in love? Are you afraid of being lonely?

You know, if you need to keep the option door open because that’s how you can keep yourself from overly focusing and attaching to someone too early, then I guess that’s what you need to do. But it seems to me wiser to learn how to date someone, and at the same time, not get too hooked early on by good feelings. In other words, I’m saying develop the inner skills to slow down and create appropriate boundaries, instead of constantly jockeying options to keep from getting sucked in prematurely.

The more you take responsibility for your decisions and emotional responses, the more likely you'll attract someone else who does the same.

What do you think about all of this?


  1. I tend to take my time regardless when it comes to hiding dating site profiles, partly for the "been burned in the past" thing, and partly because I know that I have a tendency (apparently, typical of a Horse like me in Chinese horoscopes) to jump straight into each new relationship and assume that "this is going to be The One", on the basis of very little evidence. So I know I have to take my time to figure out what's really going on relationship-wise before I'm ready to commit and say for sure "this one is someone I should focus everything on". The temptation for me is to go all-in with everyone, and get hurt a lot each time it turns out it's not really that serious.

    Which isn't quite the same as "keeping the option door open to slow myself down", but rather, the techniques I have for internally slowing myself down mean I have to take that extra bit of time to calm down and figure out what the underlying intuition is telling me about whether to pull the option door closed or leave it ajar.

  2. Well, it makes sense to me if you're aware of the tendency to jump in, to check in on yourself and slow things down however you can. I actually tend to move slower in general as well, but probably mostly because I like to know someone more before leaping in. I have been burned by leaping in as well, but it's not an overall tendency for me.

    Clearly, from all the stuff you write, you aren't treating dating flippantly, or ignoring your role in what happens.

    It's that ignoring one's own role, and trying to manipulate external conditions, that I'm responding to with posts like this. People making comments like "I tend to jump in too fast, so instead I'll date lots of people and keep my options open." Which makes me think "Are you just using some of the people you're dating to deal with your tendencies?" Because when I hear someone say they have been dating 4-5 people at the same time for weeks on end, it's hard not to wonder how many of those guys or gals fall into the "I like you, but really am mostly keeping you around so I don't get hurt by one of the others" category.

  3. I have a tendency to get fixated on one person. I have ADD, and it's called "hyper-focus." I literally cannot stop thinking about a topic that interests's crazy. I was dating multiple people (cheap coffee dates, shared expenses, no physical contact) when I met my (now) fiance. I'm really glad I was dating others, he moves at a glacial pace, and if I hadn't had distractions and other possibilities, I'd have driven myself insane thinking about him. Having other eggs in my basket allowed me to think much more rationally about it all.

  4. Hmm, that makes a lot of sense, Jim, given your situation.

    I also notice, though, that the other dates you were going on were still pretty casual. You hadn't gone in a more involved and intimate direction with anyone yet.

    So, I would have approached it the same way, even as someone without ADD. There needs to be a change in direction for me - either we're spending much more time together, and/or have become physically intimate - before I'm going to close the door on other options.

    The above post is trying to separate that out from the situations where people are saying they want a long term relationship, but are choosing to have multiple intimate and involved "half-relationships," thinking that this is how to figure out who is best for them. If you are spending significant time with, and sleeping with, multiple people for extended periods of time, that's just plain muddy to me. Maybe this approach works for a few, but most of the time, I think it ends up breeding confusion and break ups.

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