Should I Date Someone Who Fits the Bill for the Ideal partner, but I Don’t Quite Click with?

You can’t get a question more perfect for the Two Chis than this. In the 2009 film Up in the Air there’s a great quote from a young go-getter whose boyfriend just broke up with her:

Sometimes it feels like, no matter how much success I have, it’s not gonna matter until I find the right guy. I could have made it work, he really fit the bill, you know. White collar, 6’1”, college grad, loves dogs, likes funny movies, brown hair, kind eyes, works in finance but is outdoorsy. I always imagined he’d have a single syllable name like Matt or John or Dave. In a perfect world, he drives a 4Runner and the only thing he loves more than me is his golden lab. And a nice smile.

Do you notice what’s lacking in this “bill”? No real mention of character or chemistry. When you’re young, the bill is an easy short-hand for other traits. Perhaps being a college grad indicates some level of responsibility. Or perhaps because they’re tall and like funny movies, there’s a higher likelihood for good chemistry. But if only our tastes were so simple. If only there was a simple certificate that indicated who has a good character. If only there was a simple checklist to figure out who you click with. If it were that simple, then online dating wouldn’t be such a chore.

Chemistry: The short-answer is No. An exception, though, is if you haven’t spent enough time with your partner. If you didn’t click on the first date, and they otherwise “fit the bill”, give it a few more dates to establish some basic chemistry. If after 3-5 dates, you don’t have any natural flow with your partner, then it’ll be a long-shot for the two of you to have good chemistry. Continuing to date at this point would be akin to stringing your partner along.

Character: It could be that the bill you have in mind is more sophisticated than the one I quoted above. Instead of seeking superficial traits, you might be seeking solid partner, someone who is nice, caring, and respectful. In a way, the indicators of good character mentioned in this book are like a bill.

If someone fits this bill, but you don’t have good chemistry with them, you should still leave. Without the chemistry component, there’s no real foundation for love. It’s like falling in love with a great statue. This person can take care of all your so-called needs, but they won’t keep your warm at night. There’ll always be something missing in your life. How can you spend thousands of hours with someone who you can’t lose yourself into? It doesn’t matter how high your objective opinion is of this person, without the “tsa tsa tzu” (as they say in Sex and the City), it’ll be a hollow relationship.

Maybe in old movies or TV shows, like from the 50s, they show couples who don’t exactly have great chemistry. Instead, the man marries the woman because she’s pretty, and she marries him because he’s stable. Theoretically, times were harder back then, and survival mattered more than fulfillment or happiness. But in those situations, like in countries with arranged marriages, there is no concept of choice.

The entries in this book all end with a question-mark because you are someone who has choices. And if you have a choice, you should get what’s best, which is someone with great chemistry and great character. If you compromise on any of those dimensions, even for the sake of necessity, your relationship will always be something you put up with for the sake of something else. It’ll be like a job where you punch your clock.

What if you’re desperate, though? Well, I’d argue that it’s better to be single for the rest of your life. Without good character, you’ll have to put up with their abuses constantly. Without good chemistry, you’ll have to manage your boredom constantly.

Should I Date Someone Who Is a Good Thing for Me Right Now, but Not Someone I See Myself Long-term with?

Character: If you find yourself in this kind of situation, it’s important to think about why you see this person as only temporary. Perhaps it’s because they have character flaws. You may find that they’re spontaneous and reckless, which is fun for you right now, but not the kind of thing you want in your life when you get older. That’s fine, just be sure that you’re honest with yourself and know that you are compromising on character. You should be aware of any possible consequences.

If your relationship is truly un-involved (i.e. with limited romance, limited amount of time spent together, etc.), then the character issues won’t manifest that negatively. If they’re irresponsible, that’s fine, because you don’t really depend on them for anything. If they’re uncaring, that’s fine, because you don’t take too much stock in their opinions at this point.

But as a general rule, anybody who plays an important role in your life should have good character, whether it’s a roommate, business partner, husband, wife, or best friend. The closer a bad character is to you, the more likely random problems will spring up in your life. Even if you’re just seeing someone casually, they’re probably close enough that you should hold them to the same high standards.

Let’s say you’re just casually seeing someone, but you find out they’re irresponsible. When they get into in trouble, like in a drunk-driving accident or in a bar fight, do you really want to be associated with any of that? Or let’s say they’re untrustworthy, they might become quietly attached to you. Do you really want to deal with someone who might lash out passive-aggressively?

So, if it’s truly something “just for now,” and unless it’s super-casual, you should still ensure they have a good character.

Chemistry: Perhaps you’re considering something temporary because you don’t have that much chemistry with this person. This person doesn’t excite you romantically, perhaps, but is exciting physically. This is tricky, because a lot of the gestures of love carry an assumption that each partner feels very highly about the other person. How would you feel like if the person you were sleeping with felt the same way about you? What if they enjoy your company physically, but intellectually find you inferior, and therefore don’t consider you marriage-material? That doesn’t sound like someone you would exactly want to snuggle with.

So, in conclusion, you should still seek good chemistry and character, even if your relationship isn’t long-term. If you still decide to compromise on either dimension, just be aware of what the risks are.

Should I Date Someone Long-distance?

Chemistry: Chemistry can still exist in a long-distance relationship. A lot of what makes you feel good in a relationship is the idea you carry in your heart about who your partner is. Knowing that someone great is into you and waiting for you, is enough to keep many people going every day. If sex is not a huge part of your basic needs, then perhaps the great conversations over the phone with your partner are enough to keep you satisfied.

There’s two kinds of long-distance, though. If the long-distance situation is temporary, like if they are finishing school, then you should be willing to accept a lesser amount of chemistry. If you know there is a life of good character and chemistry waiting for you down the road, it might be worth it. On the other hand, you may find the experience of not physically having your partner with you too painful. If you aren’t really enjoying life or you feel too compelled to stray, then you should probably not take on this kind of relationship.

The other kind of long-distance is one that is semi-permanent. Perhaps they are in the military or travel a lot for business. In this case, you should make sure that you feel a 100% great chemistry in this situation. Perhaps you’re an introvert and don’t need a constant amount of face-time to feel fulfilled, then this might be a perfect arrangement for you.

Character: The fact that your partner is in another city probably doesn’t have any character implications. But a partner’s interest in long-distance does beg a question about how interested someone is in a real relationship to begin with.

Perhaps your partner is uncaring, and long-distance makes it easy to avoid worrying about someone else’s emotions all the time. Or perhaps they don’t want the responsibility of having to attend to someone’s needs all the time. When your partner lives close to you, they are more likely to want to come over and do activities together. So if someone is seeking something long-distance, make sure that they still ultimately want a real relationship, one with real responsibilities and with real emotional needs being fulfilled.

Should I Date Someone Who I Fight with All The Time?

Chemistry: I imagine that this is a very stressful situation to be stuck in. Even if you have a great rapport when things are good, you should factor this stress into your overall feel and chemistry of the relationship. Take into account both the intensity and frequency of the fighting. If you fight so much that most of your nights are sleepless, and you’ve ruled out the character considerations below, you should probably leave, and get your life back.

You should leave not just for your own sanity, but for the sake of having quality relationships. You really want to enjoy your partner with little or no reservations. And so if you flinch every time you’re around your partner, or you’re constantly uneasy because a fight is always around the corner, then unless you’ve ruled out the character considerations below, you should leave.

Character: Perhaps the things you are fighting about have to do with character issues. If, for example, you keep fighting over the fact that your partner talks over you and treats you like a child, then perhaps your partner is disrespectful or uncaring, and doesn’t have a good character.

Perhaps the way your partner fights also indicates character issues. Are they spiteful in the way they argue, belittling you or denying your own emotions? Are the positions they take fair, or do they constantly have a “my way or the highway” attitude?

Some people fight all the time because both sides love each other so much. You may, for example, be struggling to keep a job to support your partner, and so when they criticize you for working too much overtime, it hurts you deeply and it all comes flowing out in a fight.

If this is the case then you might want to stick it out and figure out how to communicate. It may take considerable time (maybe 1-3 years even) to figure this out, but if you otherwise have good chemistry, then it might be worth it to sail through all these fights, if it means finding a keeper.

Should I Date Someone Who Is My Friend’s Ex?

Of course a lot depends on how close you are to this friend, how long it’s been since they dated, how close their relationship was, and what lingering feelings there exist now. Since I can’t possibly answer every situation, let’s look at what the possible character implications are in the worst-case scenario.

Character: It’s possible that your partner is showing an uncaring side. They may simply not care about whose feathers they ruffle by dating you. It could also reveal dishonesty. Perhaps they still have lingering feelings for your friend, and are dating you to indirectly retread old territory. It certainly brings up possible respect issues, because there are some unspoken rules about dating an ex’s friend, and violating them is possibly an act of disrespect. And lastly, it’s possibly irresponsible, since it could lead to a split between you and your friend.

That’s a lot of possible character issues, but the keyword is “possible”. Like I said at the beginning, it depends on the actual specifics of the relationship. I would see to what extent your potential partner is careful or aware of the delicate situation. If they’re brazen about it, then watch out, they will likely be careless with your heart down the road.

Chemistry: It’s possible that chemistry could also push you away in this situation. There’s a saying, “Don’t shit in your backyard,” and so the relationship could end up stinking if it feels like you’re dating too close to home. Or it could be irritating if the topic of conversation always returns back to your friend, or if dating your friend’s ex creates an awkward love triangle. You may want to let this dimension play out, though, as you may have your own unique chemistry with this person.

Should I Date Someone Who Is Depressed?

I read a study saying that a major factor in your happiness is the happiness of your partner. Now, this doesn’t mean you should abandon people who are unhappy. Some would argue that suggesting this is a form of discrimination. This is why it’s better to look at just character and chemistry, which is a very fair way to judge relationships.

Character: Responsibility - Despite all the burden depressed people carry, is your partner still a responsible person? One of the hallmarks of depression is being so burdened with emotion that you can’t do basic things, like get out of bed to go to work or eat. But just because someone has this problem, it doesn’t necessarily mean they’re an irresponsible person.

Caring and Fairness - It’s easy to get wrapped up in your own emotions when you’re depressed, so I would ask if they’re still compassionate and caring of the emotions of other people. Also, do you find that you’re dealing with their emotional needs all the time, or is there still a lot of room for you too? If not, then they might be just be selfish.

Chemistry: Perhaps you find a lot of enjoyment being a care-taker and you love feeling needed. Or maybe you’re depressed yourself and misery loves company. Unfortunately, if your chemistry is based on that alone, what will your chemistry become when your partner recovers? You should make sure you have a total chemistry with your partner, not just when you’re dealing with their depression. Because if you’re enjoying dealing with their depression, then you’re operating under a somewhat perverse premise. Supposedly, you’re giving advice and supporting them in the hope that they will eventually get better. Yet, at the same time, you’re in love with the state that they’re in now, not the state they’ll be in the future.

Should I Date Someone Who Is Too Serious?

Chemistry: If you are dating someone who is “too serious,” then there must have been something initially attractive about the seriousness. Maybe their intensity meant super-romantic dates. Or maybe it means your partner is very successful because they take their work seriously. However, something must’ve triggered or annoyed you recently, and perhaps your bubble is now bursting. So don’t judge your relationship by your early chemistry, but rather by your chemistry today and tomorrow. Do you still really enjoy nearly every minute with your partner? Is their seriousness making it a chore to be with them? Or is it just a matter of random annoyances here and there?

Character: A more serious person probably takes things like trust, respect, and responsibility very seriously. So consider that this is likely a good benefit to dating someone who is “too serious.” However, it’s important to make sure that their seriousness isn’t a cover for actually having bad character traits. There are many people who exude a lot of intensity or righteousness, but it’s simply a way to push the attention away from themselves and make other people feel guilty.

An excess of seriousness can also lead to poor marks in fairness and caring. If your partner is constantly emphasizing the way things should be, taking on a “my way, or the highway,” attitude, then that is selfish. Even if you make mistakes, you should still be getting your way roughly half-of-the-time. Also, if they annoy people around them with their seriousness, then it shows they don’t care about other people’s enjoyment.