Should I Date Multiple People at Once?

“I can’t imagine dating more than one person at a time. That sounds exhausting!”

“I would feel like a player if I were seeing more than one person at a time.”

“What if my date found out I was seeing other people? How would they trust me?”

As a science-based certified dating and relationship coach, I often hear concerns about whether or not it is acceptable or advisable to date multiple people at once. In this article, I want to share a scenario where dating multiple people is not only appropriate but it is actually advisable.

Jumping in too quickly

I had a client, let’s call him Charlie, who was extremely lonely and looking for a lady to do fun things with and establish a romantic connection after a messy divorce. Charlie had not put much time into discovering his own likes and interests; he spent most of his time in a routine of work, gym, and household chores. Before his divorce, his wife kept an active social calendar for both of them. Her friends would all get together, and the husbands would hang out and have surface-level conversations. If Charlie tried to talk about anything real with this group of guys, they would crack jokes or change the subject. Charlie really hadn’t felt heard or seen in a very long time, if ever.

When Charlie started dating, he would share all about his divorce and very personal issues in an effort to make a quick connection. He was desperate to feel known by someone.

Because of this, anyone who seemed remotely interested after he unloaded all his personal issues would be showered with lovey-dovey texts and romantic gestures in an effort to push a connection along in the hopes that this would finally be the end to his loneliness.

Time for a pattern shift

When I began coaching Charlie, I quickly realized that he was not in the driver’s seat of his own dating journey. He didn’t really know himself, and he was looking to be chosen instead of being choosy. He would jump into relationships right away and feel an extreme sense of rejection when they ultimately fizzled out within weeks or months of starting. Charlie needed a change in his dating patterns.

Old-fashioned values

As I got to know Charlie, I learned that he and his ex-wife had married very young. He met her in high school, and they married in their early 20’s. They had a very traditional courtship. They got to know each other because they shared a class, grew fond of each other and eventually started dating exclusively without ever feeling the need to meet anyone else in between. Charlie mentioned that he is proud of his old-fashioned values and that he knows how to treat a lady.

Navigating the modern landscape

What Charlie didn’t realize, but I could see as an experienced coach, is that the set and setting of how he can meet people has changed dramatically, and the way it worked before was not working for him anymore. I needed to slow him down and have him take the time to get to know a variety of ladies, while actively trying to discover what his personal likes and dislikes are. I also encouraged him to join groups and activities where he could get to know people organically, which would mimic the way he met his ex-wife. Not to mention give him the opportunity to meet some new platonic friends to fill up his social calendar.

The benefits of dating multiple people at once

While it may not be right for everyone, dating multiple people was the change that Charlie needed. We discussed the 3-date rule, which encourages people to go slow and not make a decision about whether or not to continue seeing someone until you have gone out at least 3 times.

I encouraged him to be up front, if asked, that he is enjoying meeting and getting to know different women without jumping into a relationship too quickly.

I assured him that people who are looking for an intentional relationship rather than a band-aid relationship will appreciate the transparency. He would let his dates know that he was truly and intentionally taking his time in an effort to meet someone with shared values and goals, and that discovering this alignment takes time. He stopped over-investing financially with big gestures and learned to save the majority of conversation for when he was in person with a date.

He learned not to overshare and to just be curious about what points he connects with different ladies on, and he got to know himself better in the process!

A happy ending

After going on many dates and making new social connections through group activities, Charlie honed in on what aspects were most important to him in a committed relationship. Once he identified what his needs and non-negotiables were, he recognized the kind of alignment that could go the distance when he met the woman whom he would eventually marry. He had a feeling on date one, but took his time. They went on several dates and decided to become exclusive after 2 months, even though both of them had already stopped actively looking.

In conclusion

Dating multiple people isn’t right for everyone, but sometimes it can help us overcome negative patterns that keep us in a rut of accepting partners that aren’t actually aligned with who we are and what we want out of life.

Need help determining if you need a new dating strategy? Contact me for a complimentary consultation.