Top 5 Rotational Dating Strategies

Disclaimer: All names mentioned in the following article are fictional for privacy purposes. The ideas outlined are solely based on personal experiences, and I do not guarantee their effectiveness until you have inserted your end of the bargain ;) 

As a twenty-year-old residing in downtown Toronto, I've encountered my and others’ fair share of unsuccessful relationships. I transitioned from the Hallmark-style "love-at-first-sight" romance, where he regarded me as if he had hit the jackpot, to experiences with "one-date-wonders" and individuals proclaiming a need to focus on themselves. Though brief, these romantic escapades have provided valuable philosophical insights that fuel Sunday brunch debates. Reflecting the experiences of many contemporary women, my quest for a happily ever after has underscored the significance of cultivating a dating roster. While the idea of concurrently dating multiple individuals isn't groundbreaking, my journey to mastery involved navigating numerous misunderstandings and enduring a plethora of awkward encounters.

The challenges inherent in maintaining a dating roster are myriad. You might confuse Andrew's downtown office with the location where Andy was interning. It's easy to jumble tidbits about Joe's childhood bicycle mishap with Joshua's account of a car accident, shared with you during a cocktail conversation. However, the paramount concern revolves around losing sight of the ultimate objective: discovering a compatible partner for a lasting, meaningful relationship. To effectively engage in rotational dating and achieve your relationship goal, here are a few strategies to take into account: 

One significant advantage of maintaining a dating roster is the opportunity to encounter a diverse array of individuals. Imagine savoring cocktails at a local bar with a charming bartender on one occasion, and engaging in thought-provoking discussions about the global economy with a handsome teaching assistant on another. However, not all connections endure beyond the initial spark; some might even reveal unexpected facets as time progresses. To safeguard your investment of time, effort, and even attention to appearance, it's wise to exercise discernment when crafting your roster.

A technique I employ involves crafting a checklist of 7 to 10 criteria, meticulously noted in my digital journal, to ponder post the first date. Reflecting upon this list enables an impartial evaluation of compatibility and potential. While "Marry Him: The Case for Settling for Mr. Good Enough.", a New York Times Bestseller, advocates for realistic relationship expectations, it's prudent to establish criteria slightly above the bare minimum, including a few aesthetic preferences. Moreover, seeking shared relationship goals and viewpoints is essential among your requirements.

Drawing from personal experience, determining whether a potential match aligns with your intentions becomes surprisingly clear within just one or two dates. The ability to decisively evaluate candidates, even if it entails a touch of candidness, serves to preserve your valuable time and emotions for the future. Employing this checklist approach streamlines the process by allowing you to swiftly eliminate contestants lacking the potential for a profound connection. Consequently, the criteria you've set will likely pare down your roster to a manageable 3 to 5 individuals who genuinely reciprocate your interest.

With such well-matched prospects, dates tend to evolve into more enjoyable experiences, marked by balanced conversations and fewer instances of awkwardness. This precision paves the way for smoother decision-making regarding exclusivity when that juncture is reached.

Aside from limiting the size of your roster, make sure you are on top of the game by tracking the progress. One of my go-to strategies is to organize a Google Spreadsheet to record date frequency, and meeting location, and journalize my overall feelings about a guy. I also included a scale from 1 to 10 to rate my first date, and checkboxes to determine if a second date is possible. At some points, this strategy makes my dating life more technical and methodical, taking away the enchanting aspect. However, my spreadsheet ensured that my potential partners were well-aligned with the prerequisites, which greatly contributed to the ultimate goal of establishing a long-term relationship. 

In addition, the Progress spreadsheet improves attachment issues by reminding you of the relationship’s timeline. As someone who easily developed feelings and saw great potential in very new connections, I used to jump into commitment without much knowledge about a person. Having a spreadsheet reminded me that whatever special emotions felt during our date were just a normal part of any casual connection. It also reminded my hopeless romantic nature that I had only known the guy for a couple of days and spent around 3 to 4 hours of one-on-one time with him. Hence, it is my job to maintain the boundaries and not perform girlfriend duties as a friend. 

Most importantly, keeping a tab of the dates I have gone on improved my organization skills, giving myself and potential partners a more enhanced experience. I will be able to avoid taking one person to the same location or having a waiter mistake one guy for another. Towards the end, it will be easier to make a decision by comparing everyone’s pros and cons on the same scale. This is because your good nature and kind-hearted self will not only appreciate the positive qualities but also consider and balance out the less favorable ones. 

While rotational dating is an old trick in the book, not all participants are transparent and honest about their intentions from the start. As an explanation, many claimed that they did not want to cause any hard feelings that result in losing a potential partner. However, this lack of communication can eventually cause bigger misunderstandings, as one partner might have different expectations and goals from another. Speaking from personal experience, I was shocked to know the charming research assistant who bought me coffee every Sunday was looking for a casual hookup after a month of “cat-and-mouse”. The situation could become worse after the other party found out by themselves. Even in rare cases when they don’t look forward to a long-term connection, the potential partner will feel somewhat of a disappointment or even betrayal. 

It is not necessary to clearly state your intentions on the first date, to avoid sounding like one of those love-bombing hypocrites. The prime time to discuss yours and theirs expectations would be around the fourth or fifth date. By this time, you would have been seeing them for at least three weeks, or a month. The given time frame is long-enough to establish a long-term connection, and become exclusive as a couple. On the other hand, this period is short-enough to not get disappointed when a relationship does not turned out how you expected. 

As mentioned above, you should start communicating your intentions at around three of four dates, approximately a month into a connection. While some romance novel slow burn romances are worth living for, keep in mind that everything has an expiration dates. Evidently, many articles under the key words “relationship timeline” clearly stated different phases of a relationship. These sources have one thing in common, they all stated that the length of each stage are counted by months or weeks. After a certain amount of time, a connection will eventually pass the prime point of development. As a result, you and your potential partner(s) will remain friends or a casual fling, depending on the strictness of your boundary. To ensure you are not missing out on a potential relationship, make sure you have a deadline for all the connections on your roster. Your deadline can be broad and flexible, for instance, don’t remain in the talking phase for more than a month. For those of you who are extra, you can add in a detail or two for each stage. From my personal experience, if I don’t feel the need to randomly facetime him at night after two weeks of talking, I am not that into him. 

Having a timeline prevents you from wasting your time with people whose relationship goals don’t align with yours. As a woman, the deadlines also remind you of the “If he wanted to, he would” concept. While your girly self might be drawing tarot cards, having deep conversations over brunch with your girlfriend about each of the guy, these men only take 8 minutes top to decide if they wanted to pursue you. 

One of the key to stay on a clear timeline is to have clear boundaries while dating people on your roster. These boundaries are a reminder to not deliver the “girlfriend package” without being exclusively dating. These limitations can be as simple as not being physically intimate during the talking stage, or as extreme as not staying for longer than one hour during the first date. You might choose to be flexible with your limitations, but keep in mind that these boundaries are indications of your relationship expectations. They help to remind your partner that your ultimate goal is to be in a long-term relationship and that they must furtherly pursue you in order to receive the full-glam “girlfriend package”. These boundaries also ensured that your standards are high enough to establish a stable relationship in the future. 

After three months of rotational dating during the flirty Springy months in downtown Toronto, it is predictable that most people will not be staying on your roster for more than three weeks. Most of them will choose to leave after you declare your goals, and you will also cutting some out due to the lack of consistency. You will develop feelings for one person more than the others, and ended up choosing a lottery winner at the end. Despite all the “pick-and-choose”, the relationship with your roster’s first runner up might not be as good as you expected. Up until that point, many might choose to lower their standards, and establish a new sense of reality. However, keep in mind that you can always redo a while cycle, and rotational date again until you find your Mr. Big.