Dating Multiple People (and Why You Should Be Doing It)

Finding a person that you mesh well with can take time. Depending on how you date, it can take a very long time.

When I first started online dating, I had this notion that dating more than one person simultaneously would somehow be insincere. I did my best to only talk to one girl at a time. There were times where I would end up talking to a few girls at once but this was always accidental.

With this approach, I went on one first-date every month, sometimes less. All of these dates were very stressful because of the time being I devoted just to get to the date. First date failure, whether because she wasn’t what I was looking for or the reverse, was very difficult. It always felt like starting all over and was always painful. Once I even continued to date a girl just to avoid “starting over”.

Reasons to Date Multiple People at Once

Around the eighth month of my online dating experience, I gave up on my “sincere” method of meeting girls and intentionally tried to meet as many girls as possible at once.

For the first few weeks, things were similar to my old method and I didn’t see immediate improvements but over time my dating life changed dramatically. I moved from one date a month to one a week and eventually was going on up to two first-dates a week.

There were several side-effects to this, aside from a busier schedule, that make me now believe this is the best way to approach online dating:

1. Better Definition

As I went on more and more dates in a short time period, I realized that what I really wanted in a woman and what I had been willing to accept were very different.

When I was only meeting one girl a month, there were so many qualities that I didn’t like that I would ignore simply because I didn’t want to have to start all over with someone else. I would continue to date someone negative or rude or conceited and would just hope that things would just eventually “work themselves out”.

All this changed when my dating schedule became very active. Breaking off communication with someone I had nothing in common with, or at least who was missing qualities I was looking for, became easy. Honestly, it was often a relief because there were more first dates waiting and I would be able to remove someone from my list of potentials.

This freedom allowed me to finally be honest with myself about what I was looking for. I stopped defending the poor qualities my dates had and started moving on. Dating in numbers allowed me to make decisions based on what I desired, not based on how lonely I was at that time. It also helped me better define what I was looking for in my profile.

2. Greater Comfort
One great side-effect to dating so actively was that I became more comfortable with dating itself. I was discovering which conversations worked better than others and was able to avoid bumps in the conversation all together.

The confusion of first-dates was disappearing altogether. I actually started to have fun. I hadn’t even thought that having fun could be a part of online dating but as I grew more comfortable, I had more fun. I still wasn’t the most confident guy (for example, I still wasn’t randomly asking girls out in public) but I was becoming very comfortable on dates, which gave the appearance of confidence.

3. Less Stress
With dating multiple women, there was always another first date on the horizon. Failure wasn’t so horrible any longer. I lost my hell-bent desire to make every date go perfectly.

When the stress lessened, I stopped paying attention to myself and started paying attention to my date. On one occasion when things were going very poorly, instead of stressing out, I told my date I didn’t think we were a great match but that we could still have fun over dinner. She seemed relieved and agreed to try to enjoy the dinner. We did have a nice time that evening and then proceeded to never speak to each other again.

Failure became a part of dating, neither good nor bad; just a part that has to be accepted.

Photo by Sklathill
4. Better First Impressions
This was a direct result of having less stress. As the stress began to lessen, I started representing who I was much better.

Early on I was always in a panic-mode: trying to make sure everything went perfect on every date, overly concerned about the happiness of my date, worried about the impression I was making and so on. Looking back, this only made my dates uncomfortable and left me looking either weird or desperate.

When I had multiple dates lined up, I found myself very relaxed on each date. Once I relaxed, I felt much better about the impressions I was leaving. Even when things didn’t work out and my date was not interested in seeing me again, at least I knew we just weren’t a match instead of wondering if I had only done “better” would she have liked me? When I was relaxed, there was no “doing better” or “doing worse”. There was only who I am.

5. Improved Odds
If you believe that you can get along with anyone out there then dating few people could work for you. For the rest of us, the biggest part of find that special someone is opportunity.

To put it another way: imagine there is a room with 100 singles of the opposite sex in it and in this imaginary room there is one person who is a “match” to you. Using my original method for dating (one girl a month at best), my odds of meeting that special someone were very low and theoretically it would have taken a very long time to meet her. Odds are years and years of dating.

The issue here is the length of time only identifies part of the problem as it assumes that the “match” won’t move on to something else: a new job that she wouldn’t have been taken had she been in a relationship, settling for someone just to not be alone, etc. Taking too long doesn’t just mean you’re looking longer. It can mean missing opportunities altogether.

I believe that dating many people improves your chances in two ways: you have a better chance of meeting someone who you are looking for but you also potentially avoid missing out on someone who may move on if you never get around to meeting in the first place.

Let’s take the example to the odds example to the other extreme: imagine that after a maximum of five dates everyone meets their special someone, guaranteed. Some may meet on the first date, some may meet on the third but no one ever needs to go beyond a fifth date.

Living in this imaginary world my question is this: how quickly would you go on your five dates? Would you attempt to meet your special someone sooner or later? If later, why date online at all? You’re risking meeting that special someone before the time you’ve appointed “appropriate”. If sooner, why wait by going on few dates? It seems logical that most people would go on their five dates as quickly as possible when desiring a relationship. I think the real world is similar, if not so simple!

6. Get Your Money’s Worth
If you are using online dating, chances are you are paying something. When I was meeting one person a month, it cost me exactly the same as when I was meeting seven a month. Why not get your money’s worth and meet several people?

---

After dating in numbers the benefits are very clear to me. However, every time I have offered this advice to friends it has been rejected as “not for them”.

There seems to be a general aversion to this kind of dating. This is why I laid out all the benefits above: just in case the everyone else is just like my friends. Just give it a try. Date as many people as you possibly can without getting confused. For some of us, that might be three. Other may be able to date a dozen and keep everything straight. I had eight first dates planned once and found it was way too much for me (fortunately none of the dates ended with me confusing one girl for another!).

In the end, I found that five worked best for me.Sometimes you won’t be able to date a lot of girls at one time. There may not even be two people you’re interested in with the service you use! If this is the case, chances are you are too picky so try to be open-minded. Take a few risks – ask out a few no-picture profiles. Yes, you’ll be living on the edge and, yes, you may not be attracted but at least you’ll be out there.

If all else fails, sign up for a second service somewhere or at least check out the members. In the case where you are contacting people but getting fewer responses than you would like, understand that it takes time. It took around five weeks from when I decided to date multiple girls to when I actually was dating multiple girls. It takes a little guess work but you should be contacting people until you feel that you are at your max for dating-without-confusion. When you remove someone from your list of potentials, start contacting people to fill that spot. This is tricky so be careful: play your cards wrong and you may find yourself with an empty list of potential dates or a list so large you can’t handle it!