Should You Keep Dating or End It?

Here are some considerations for one of the most common relationship quandaries.

Posted Dec 31, 2020

I've worked with many people trying their best to navigate the chaos of the dating scene, which was often stressful and confusing even before the days of a lockdown. As many questions as can arise in the early stages of getting to know someone (Should I text them again? Was that topic too intrusive? Is this appropriate to wear?), perhaps the most fraught is whether to continue seeing someone that you have mixed feelings about. How many dates is enough before you know that it's not going anywhere? What is a red flag, and what is not? How much spark can grow later on, when it is absent in the beginning? 

To help with the calculus of "Is this going anywhere?" I've highlighted some common guideposts that are worthy of reflection. While no one but you can determine for sure if you should continue seeing someone, these considerations will help you on your way to making the decision. 

1. Is there a foundation of kindness?

Much research has shown that kindness is one of the most important foundations of a long-term relationship. If you don't have a strong sense of that in the person you're dating, it's important not to make excuses for its absence. 

2. Is there evidence of integrity and honesty?

Some of the most important red flags early on involve dishonesty and a lack of integrity, like misrepresenting oneself. It may seem small at the time, but often tiny things can add up to a big problem if they're part of a pattern. 

3. Are there common interests and activities?

It's not imperative that a couple share all the same interests and hobbies—in fact, that could be a problem in and of itself. But if there is virtually no overlap, it's going to be difficult to find ways to spend time together that are mutually enjoyable.

4. Are values on the same page?

What's most deeply important to you in life will guide much of your behavior over time—what you seek out to find meaning, what brings you joy, what actions you take in difficult situations, and what your overall goals are. A mismatch in this can cause heartache later. 

5. Is there a spark or the potential for one?

Perhaps one of the most difficult calculations involves how much romantic spark—or sexual attraction—there needs to be in order for a relationship to work. Though physical chemistry can most definitely grow over time, it is of course helpful if there is at least the hint of it in the beginning. 

6. Does the conversation flow well?

Nothing spells a dead end of a dating experience quite like a lack of conversation. Does the person show interest by asking you questions? Does the back-and-forth feel comfortable and engaging? Nervousness is normal, but a total lack of things to say to each other can often spell doom. 

7. Is there motivation on both sides to communicate and make plans?

In the dating dance, it's often stressful to figure out how frequently to make contact. And though it's easy to fall into a pattern of one person being the initiator, there should clearly be responsiveness and energy being put forth on both sides. 

8. Is there respect and the beginning of trust?

Being treated with disrespect when both people are supposed to be showing their best selves is definitely cause for concern. And while the beginning of a dating interaction is too early to build much trust, you should at least feel the potential for it. 

9. Do you enjoy your time together?

It's a simple question, but it's one that often gets lost in the dating calculus: Do you like being with the person? Don't overthink it or make excuses—this is a must. 

10. Are you truly interested in getting to know the person further?

You might like the person plenty, but one thing that makes the difference between liking and liking is the desire to learn more and get to know the person more deeply. Are there layers there that you are looking forward to uncovering? if not, then it's hard to sustain much excitement. 

11. Do you feel increasingly comfortable being yourself?

It's normal in the beginning of dating to try to put your best foot forward, to the point of not "letting it all hang out." But you should start feeling like you are more able to be yourself over time. If that's not there, pay attention

12. Is there a match in responsiveness and communication styles? 

If one person wants to text multiple times per day while the other is content with once a week, or if one person wants weekend plans set on Monday whereas the other bristles at committing to anything before Friday, that can be a problem. 

13. Are attitudes toward sex in the same ballpark?

Sex is often a big source of conflict for couples. If there are glaring discrepancies from day one in terms of how important it is, what you feel is "right" versus "wrong," or just your overall desires for it, that's worth paying attention to.

14. Are you both looking for the same type of relationship?

Too many times, I have worked with people who will begin to make excuses for the fact that their potential partner has made it clear that they are not looking for the same thing—whether that is monogamy, marriage, children, or a lack of all of that. Don't convince yourself that you'll be able to change them just by getting them to love you. 

15. Are your social lives compatible?

Of course, your friends and your potential partner's friends need not be best buddies, especially right away. But if there is severe incompatibility—you can't stand the attitudes of the people your potential partner loves best, for instance, or you are very much a hang-out-at-home person, and they are a party-all-the-time person—it's realistic that this will cause fraying over time.

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