Should I Date Someone Who . . .

Should I Date Someone Who Is Too Laid-back?

Chemistry: Their lack of seriousness is probably a turn-on. Perhaps they’re spontaneous or perhaps they listen to everything you say without judgment. But your slacker friend may become less charming when you try to do more complicated activities together like plan a trip. So, one way to figure your chemistry out is to have more varied experiences with your partner.

Other than that, though, the chemistry dimension is pretty easy to evaluate here. You either enjoy being around laid-back people or you don’t. So you should probably focus on the character questions.

Character: Does their laid-back nature extend to a lack of responsibility? Do they have trouble keeping appointments and holding onto jobs? Or does their laid-back attitude have less to do with laziness and more to do with having a relaxed mindset?

Next consider the fairness questions. Is being laid-back a cover for letting everybody else do all the work? If they’re a free-loader or a leech, then this is minus points in the fairness character trait. Don’t expect them to make compromises or cater to your needs in a more committed relationship. On the other hand, if being laid-back is their way of letting other people take the spotlight and have a chance to lead, that’s plus points in the fairness category.

Another question to ask is, Are they apathetic about the world around them? Citizenship is a commonly forgotten part of the character dimension, but if you want to eventually start a family, you’ll want a partner who can serve as a role model or who is interested in community activities. On the other hand, they may be very aware of the world or community events, but just choose not to get overly stressed or excited about them.

Should I Date Someone Who Is Really Messy?

I have another saying, “The roommate who is cleaner is always oppressed.” I don’t believe this is a hard-and-fast rule, but it has some value.

Chemistry: Rather than judging a messy partner outright, why not see how the messiness is in action and go on a trip with them. If you find that the trip is less fun for you because you’re grossed out the whole time, or you’re disgusted by your partner’s habits, then imagine what 365 days of that, year-after-year is going to be like.

Character: Is the messiness indicative of irresponsibility? Are they also lazy or always running late? Do they have trouble keeping jobs or following up? If so, then that could come back to bite you when more serious responsibilities become the norm in your relationship.

The way in which your partner deals with your cleanliness is also a good prism by which to view their character. When you object to how dirty or messy things are, does your partner respect your opinion? Are they fair in their response? I’m a clean and organized person, and I know why I’m that way. When I see disorder, I feel motivated to correct it. If something’s out of place, I can’t help but put it back or make it right. I feel unsettled when my environment is unsettled, and I get satisfaction returning things back to equilibrium. A messy person doesn’t feel the same unsettling feeling, nor do they get the same motivating kick that I would get.

Having said that, even if a messy person can’t change overnight, there’s enough hacks and tricks that your partner can do to make your life easier. Let’s say your partner leaves dirty socks everywhere. You may not be able to convince them to stop doing that altogether, but you can probably convince them to at least put them in a pile in one corner or somewhere out-of-sight. If they can’t at least do some small favors to make coping with a messy person easier, then they’re not being fair, nor caring, nor respectful.

Should I Date Someone Who Is Way Younger Than Me?

This is probably coming from a man dating a younger woman, but the ruling here applies to both sexes. First, let me state the famous unofficial rule in case you haven’t heard of it. It’s the half-your-age-plus-seven rule. Take your age (let’s say 34), halve it (so 17), then add 7 (so 24). Therefore a 34-year-old should only date someone 24 years or older. Take any age, and you’ll find this formula sort of “make sense” in most cases. But why does it make sense?

Chemistry:The Two Chis Principle will roughly come out with the same answer (give or take a few years). The most obvious concern is chemistry. If you’re dating someone a lot younger, there’s a good chance you’re very much drawn to the other person’s good looks. The amount of magnetism you feel for your partner is a crucial aspect of chemistry. But you have to take a 360-degree view of your chemistry in order to know how well the relationship will succeed. Are you magnetized to your partner’s mind? Do you feel warm and stimulated in conversation? Do you feel great going on long trips with your partner? The most obvious problem with an age-gap is whether you’ll have enough in common to have chemistry beyond the simple age-difference attraction. So for example, just because you’re an older dashing gentleman and she is a nubile, innocent beaut, it doesn’t mean you’re a perfect match.

There are also some social considerations. You shouldn’t care what other people think, but you need to be practical, and see how it feels like to be with your partner in social settings. Do you feel uneasy when you and your partner socialize in groups? If so, gauge how much it actually affects how you feel about your partner. Do you find that it makes you want to cling more tightly and say, “forget what everybody else thinks,” or do other people’s doubts become your own?

Character: There are some character issues that are natural to youth, such as lack of responsibility or being overly selfish. However, relationships can bring out the best in people, and a lot of young people are very responsible and fair, even at a young age.

With regards to trust, there’s a good chance that the young person you’re dating doesn’t quite know themselves yet or know what they want. However, since even older people evolve over time, you can’t really hold it against them. Instead, see if your partner is good at articulating their station in life. Do they understand where they’re at today, and what they’re leaning towards in the future? This takes some emotional intelligence, but it will make it easier to trust them if you know they’re open and accurate about their self-descriptions. Even young people can be self-aware and say, “You know what, I’m at a point in my life where I want to be free and travel, try different jobs, and see what happens.” The non-self-aware version will just get up, travel, and leave you hanging. So figure out what kind of partner you have.

There are respect issues too. You may command a lot of respect from your partner just because you’re older. But verify that they’re respectful to their peers as well as people younger than them. If not, then their respect for you may wither when the two of you become more familiar.

Should I Date Someone Who Is Shorter Than Me?

Chemistry: I’m not going to be naive and make a blanket statement like, “You shouldn’t care what other people think” or “You shouldn’t be so superficial and judge people like that.” Your overall attraction toward your partner is important, regardless of where that attraction comes from.

Do you still feel sexy when you stand next to them at a party? Do you still feel secure when walking on the street alone with them? If so, then congratulations, this is not a major component in your attraction for this person. I would imagine that most people overestimate how big of a deal height differences are up-front, and so I would wait for those kind of situations to occur rather than pre-judging how the experience will turn out.

Character: n/a

Should I Date Someone Who Is in the Mob or Involved in Crime?

Carmela Soprano probably should’ve read this before dating Tony, but the short answer is “No.”

Chemistry: Let’s try to base this off of the Two Chis anyway. The chemistry dimension may not actually seem like a factor here, because the fact that your partner’s a criminal is probably a turn-on for you. However, it’s likely you don’t know your partner well enough. You might be only seeing them in spurts, and so aren’t getting a chance to let the whole criminal lifestyle sink in. The chemistry you have with your partner may fade away when strange people start camping out at your house, or when you have to deal with moving around too much, or when the lying gets too stressful, or when the uncertainty gets too grating. So before you judge the relationship based on your excitement, see more shades of your partner, experience longer stretches of interaction, and then see how excited you really are.

Character: The character component should be obvious, but perhaps that’s why it needs to be spelled out. Every aspect of character is expressed in criminal behavior.

• Trust: Criminals often have to lie in order for their cons to be effective.
• Responsibility: Criminals expose themselves to too much risk. When your partner goes out and makes their rounds, they are willing to risk being thrown in jail and therefore, being completely isolated from you, for the sake of money.
• Respect: They don’t respect other people’s property or interests.
• Fairness: They believe their interests are so important, that they have to come at the expense of others.
• Caring: They are unmerciful and don’t care about how many hearts they have to break to get what they want.
• Citizenship: This is obvious, and while it may not seem like a big deal, think about the kind of role model your partner is. Their behavior is certainly not the type you want duplicated in your community or in your children.

After reading all this, the villain may still seem irresistible. If so, I would try to imagine what it would be like on the receiving end of all of those transgressions. How would it feel if they didn’t care about your feelings? How would it feel if they burned you with dishonesty?

Should I Date Someone Who Is with Someone Else?

No.

Well, okay, maybe.

Chemistry: The chemistry you have with your partner may have a lot to do with the fact that they’re with someone else. Your partner’s excitement may be rubbing off on you. Most people with affairs find that sneaking around adds a lot of spice to their lives. Their excitement may therefore be rubbing off on you. But will it be exciting once they’re not with their significant other anymore?

Do you only see your partner in spurts here and there, when they have a chance to sneak off? If so, you might be seeing a very limited side of their personality. Try to pin your partner down for longer stretches of interaction or for more typical/”boring” couple activities, like having dinner and a movie. If you’re basing your whole relationship on late-night sushi and random romps every couple days, then you have a skewed view of your actual chemistry with this person.

Character: This should be easy to address. Cheating is untrustworthy. It’s disrespectful. It’s uncaring. It’s unfair (the cheater gets the full attention of two partners, while as the cheated gets only half of one). And if there are kids involved, it’s very irresponsible. So, if you’re with someone who is with someone else, it’s very likely they have larger character flaws. Good luck in dealing with those character flaws when and if they end up with you.

However, there are some caveats. Breaking up is hard, and many relationships are as good as finished anyway. A good example is someone who has been separated for a year, but is still married on paper. Another is someone who has stopped living with their long-term boyfriend/girlfriend. If your partner has already made material progress toward breaking up, then they might be as good as single. Your partner loses some points for not having the will to make a clean break, but it doesn’t necessarily indicate a poor character unless there are other warning signs.

Should I Date Someone Who Works With Me?

It’s important to keep in mind that your specific case may have more practical considerations than the Two Chis. My first questions would be, “How much do you care about your job?” and “How large is your company?” If you care a lot about your job, then you should be really reluctant to consider dating in the workplace. If the relationship goes under, then you’ll be losing both a partner and a potentially rewarding career. If the company is larger though, then there may be more opportunities to move around should the worst happen. Having said that, dating within the workplace is extremely alluring and one of the most frequent places where people nowadays say they met their significant other, so you should never say never.

Character: If the person you’re dating is your superior, then that should raise a flag. It’s not an automatic deal-breaker, but you have to see how this reflects on their character. Do they have a prior history of picking up subordinates from the office? If yes, then your potential partner doesn’t seem to have a strict enough moral compass to keep themselves in check. There is a spoken and an unspoken rule about superiors dating their subordinates, and so your superior should only pursue something with you if this time is really an exceptional case. Even if they do decide to proceed, they should at least appear to be cautious and show reservations.

If they’re flagrant about it, and have dated subordinates before, then they probably lose points on the fairness aspect of character. Superiors have an automatic power advantage, which is very easy to abuse. If they seem casual with using that power, then you may have trouble getting what you want or finding compromise later down the road.

If the person you’re dating is a subordinate, then that should raise a flag as well. Again, dating within the workplace is like the Rubicon, it should only be crossed in exceptional circumstances. Does your partner have a prior history in the workplace? Are they very carefree about it, throwing caution into the wind? If so, then this person is someone who is potentially very irresponsible and/or uncaring. This is someone who doesn’t care what other people think of them, and so how can you be sure they’ll care what you think about them?

Chemistry: Dating within the workplace is usually extremely appealing. So, I would be curious to see what your interaction is like outside of the workplace setting. If you go on a trip together (for something non-work related), are all the sparks still there?

Should I Date Someone Who Makes Less Money Than Me?

Chemistry: This question is most likely coming from a woman in a heterosexual relationship. I would imagine that for you, it probably doesn’t bother you to make more money than your man. It probably isn’t a libido-reducing aspect like it could be for him. You should watch how it affects your partner’s attitudes toward you, though. If your partner can’t give a 100% because they have some innate need to be the breadwinner, then that could be a problem. Most couples want both partners to feel confident and free in the relationship (even if one is more dominant), and so you may not reach the full enjoyment potential in this kind of situation.

Perhaps, though, you’re asking this question because you’re worried that your partner doesn’t make enough money and will have to rely on you too much. You might be an over-achiever and you might like being surrounded by peers. If your partner is a slacker, and that lifestyle is reprehensible to you, then that is the turn-off, and your chemistry should suffer accordingly.

Character: So the question here is, then, what does your partner’s earning potential show about them. Usually it’s a matter of responsibility. Do they earn less because they just can’t get their act together. If they’re irresponsible in other parts of their life (like with excessive drinking or constant flaking out), then this should be a warning sign. There are many other responsibilities in a relationship besides financial, and so it’s going to be horribly vexing when they flake out on you down the road.

Should I Date Someone Who Makes More Money Than Me?

Chemistry: This should not be a deal-breaker right off the bat, unless you have a very strong need to be the main breadwinner. If just the thought of making less money than your partner repulses you immediately, then it’s probably not worth even trying. Most people are not like that, though, and so I think you should give it at least a month to see how your attitude evolves. Maybe you’ll feel less insecure about the disparity over time.

Maybe you’re worried that you’ll be pushed around. Why not try it out and see if that happens? If so, then your partner is unfair and disrespectful, and that’s a character issue about them that you just learned. Just because they make more money than you doesn’t guarantee they’ll be bossy.

Maybe you’re worried you won’t feel as good about yourself. Why not try it out, and see if that’s the case? When you go to parties with your partner, is it impossible for you to escape feelings of weakness? If so, then it’s just not going to work for you.

Maybe you feel like you won’t be able to have as much to say in important decisions. Why not try it out, and see what kind of natural roles crop up? Maybe you’re used to taking a certain role in previous relationships, but will be pleasantly surprised when you don’t react the same way in this relationship.

Maybe you feel like it’ll make you feel too subordinate and that will lower your libido. Why not try it out, and see if that’s the case. Maybe you discover everything works just fine, and you feel more comfortable than you thought you would have.

So in other words, let the chemistry play out, rather than pre-judging based on this one feature.

Character: Making more money doesn’t automatically imply a worse character, but it does provide an opportunity to verify it, as mentioned above. After all, they say power corrupts. So check to see if money isn’t corrupting your partner and they aren’t abusive of their power.