Dear FT,

So I’ve been dating for quite some time now. At first, I was mostly casual and I was ok with that. But now I’m at an age where I don’t get much joy from just casual dating. I know a lot of people say they start out this way, just hooking up, and then it becomes more, but for whatever reason, I just don’t think I’m good at that. It ends up making me feel confused. And it’s hard for me to compartmentalize my feelings.

That being said, I ran into a guy recently who I’d always had a crush on, who also said he’d always had a crush on me. Which is exciting. But he’s newly single and made the comment that he’s not looking to jump into a relationship. I totally understand, but … knowing that I am looking for a relationship, I wonder … should I even consider dating a guy that says he’s not ready for a relationship if I know that I am?


Dating with intent



Dearest Dating with Intent,

Ahhh, the joys of dating in today’s society, whereby we want these momentary, superficial connections without any of the sludge that potentially comes along with a deeper connection… We’ve let Facebook determine how we want to interact with others, sadly. We want your highlight reel, but we don’t want to be in your pictures. We want the occasional updates and your sporadic presence, but we don’t want to change our relationship status… A snippet here, an update there – let me have the “good,” while casting aside any of nitty-gritty of you…

Which is fine, and totally okay, if that is what you’re genuinely after, you’ve made this clear, and the other party has consented to this arrangement (problem is, often, we aren’t offered the option to consent to this up front and trudge along blindly with someone until the intent is made clear and ultimately hearts are hurt).  

But, we are all free agents able to choose what kinds of interactions we want with others and imposing boundaries around the kinds of interactions we don’t want. The truth of the matter here is, we should respect the boundaries of others while ensuring the boundaries of our own remain intact. And it sounds to me like this guy has implied a boundary: we can have a momentary connection (and let’s be honest, what I suspect is sex), but I will not be invested into knowing and caring for your soul. Basically, don’t expect to get from me what you’re craving – which is what I assume you’re wanting, Dating With Intent: two people working together to learn each other and eventually committing for however long, to become partners in life.

On one hand, it’s hard to know if people really mean what they say, though. Shit, as you mentioned as happens with many others, I, too, started off with my guy as a causal connection. Albeit, I was very clear that I was only into casual when I met my guy and he clearly expressed the same. And I may also mention, he had just 2 months prior, ended a 3-year relationship with someone else. However, we both stated clearly to each other that we weren’t looking for a relationship, But? We both also clarified if one (a relationship) should come about, then we’d be open to that too. And, well, that was exactly what happened. (However, my gut instinct is that this is not a similar situation with your crush – but let’s move on.)

To be fair, we should do the due diligence to rule the option of a possible relationship out, right? I mean, given my history with my current guy, from the sound of it, I can’t officially deduce that your crush was absolute on his boundary at this point. And as Tim Ferriss quotes often, “if you want better answers, ask better questions.”

“I’m not looking to jump into a relationship” doesn’t quite close the door, to me. Honestly, “I’m not looking to jump into a relationship” is exactly (in my opinion) what every relationship should start out being. Because it’s basically stating, “I’m not looking to jump in a relationship with you, yet.” And to be fair, in the beginning stages of getting to know someone, we all don’t know if we want to jump into this relationship. We don’t want to buy the car before the test drive. So, perhaps a further conversation is in order on how open he is to one potentially developing. Because his ultimate goal may be to eventually find someone he can share a life with, he just may really desire a series of non-committed experiences before that happens. To which case, if you wanted, you can then close the door for now, but offer to have him hit you up and see where you’re at after he’s got this season out of his system.

However, perhaps he says, “No, no, with the right person, I’d be open to being in a relationship again,” or something to that nature. Well, then, this is a proceed with caution situation… And in order to do that, I might bring up one consideration you’ve implied with this…

You mentioned you get “confused” after you have implied “hooking up” with guys in the past. Apologies if this is misinterpreted on my end, but I am left to assume “hooking up” means sex. And if this is the case, do you think that perhaps you could place a “no sex rule” until a 3rd or 4th, or 5th date with him (or future potential suitors), to help you clarify if this is someone you’d like to pursue further? I think that sex can confuse a lot of emotions for many individuals, and so perhaps you can take the car out for a test drive, without putting your gas in the tank.

However… However… All this leads me to a different concern. This concern being the degree of focus to which you maintain on finding a long-term relationship. While I think it’s highly, HIGHLY commendable that you are ruling out casual experiences because they are unfulfilling and confusing, the concern that arises for me is that you’re even in a wrestle at all on whether you should date him after he (may have) clearly stated he isn’t looking for what you’re looking for. Not going to lie, this smells a little of desperation – like a scarcity mentality – that perhaps you feel you must pursue all options if you have ANY chance of finding your long-desired long-term commitment? Now, I may be wrong, but if I am hitting on something that is making you even a little uncomfortable – have you asked yourself if you’re possibly too focused on finding a long-term commitment at the expense of a happier future?

Let me roll this out with a personal example for consideration…

Sometimes when I am so focused on obtaining something, I make compromises to my detriment. In my previous job, I left unexpectedly and not necessarily at my choosing. I felt panicked, worthless, alone, insignificant. I was feeling desperation for income. All I wanted was to have a long-term commitment of income… My guy, who was willing to shoulder our financial burden, told me during this scary season to take my time, and figure out “what I really wanted” before jumping into the next thing. But so desperate was I to have steady pay, and so terrified of losing my reputation, I couldn’t see clearly to evaluate what it even was that I wanted. Cue the first job offer I received, followed by an acceptance. Ahhhh, income… relief.

Now, you only have to read a recent post I wrote on how this all turns out. Yes, I got my steady pay back, but I here I am, a year and a few months later, miserable and plotting my escape. Looking back, I deeply wished I could have come to a place of acceptance of my situation despite my agony, and taken the time I needed to really flesh out what I wanted in a career. Instead, all I could see is I needed the commitment of income. How that played out, be damned. I was convinced whatever job would give me income, I would bust my ass and give it my all, make it work, and it would be great. But that wasn’t the case. I busted my ass and felt more and more empty as the months rolled on. I sacrificed so much of my authenticity in the name of reputation and security, only to find myself having to repeat the entire situation. I am soon to leave my long-term commitment of income yet again – and I am finding myself right back in the same situation I was so desperate to alleviate before. Only this time, I am ready to bear the financially tight scenario. I am ready to take my time, and work my ass off to build something that is right for me. And I finally feel like I know now, what is right for me (or at least my desired direction).

Now, why did I go into that personal hell story? Because I am curious if you might relate…

Clearly, you are focused on finding a long-term relationship (which is not wrong). But, say this guy (or maybe another guy you meet) was looking for a long-term relationship. Have you thought about how you would react to that? Is that really the solve? Have you taken the time to vet this person to see if you are compatible? Do you know yourself well enough to heed the red flags when they tell you, you aren’t compatible? Would you really be ready to commit to pursuing a relationship before the first date? And if you did commit, would you feel confident in yourself that you are choosing someone great for you, or would you perhaps just be willing to settle for the alleviation of being lonely, at the expense of your own future happiness – just because they are willing to pursue something long-term with you in the moment?

I mean, isn’t that what dating is, anyway? Figuring out all of this? 

Yes, we all crave companionship. We absolutely do. That is not a bad desire to want to have a long-term relationship at all. But at what cost?

My actual advice here you take this time to focus on you. Find out who “Dating with Intent” really is, if you don’t already know. Find lost loves and passion projects and hobbies she may have been neglecting. Find your demons and confront them. Seek a counselor, write, dance, sing, bust ass in your (hopefully loved) career. Take a class, deepen your friendships… Explore thyself and find out why she’s so damn lovely.

Mostly, learn to be your own cherished companion instead of considering committing yourself to someone who “will have you.” Because I have a sneaking suspicion that you’re incredible. And if you find how to fill the void for yourself that you are focused on someone else filling (yes, it may not be in the way you want it filled – i.e. a love relationship), you won’t be so conflicted in trying to pursue just any guy who tosses half-assed interest your way. You won’t need a relationship anymore. You’ll be free to explore on your terms, which helps you make better judgment calls on possible suitors. And the best, most fulfilling relationships are founded when we don’t need someone else. 

So keep shooing away the men you have conflict about (of course, after clarifying with good, deeper questions why the conflict exists in the first place). Don’t settle only to find yourself miserable later on and right back in the same situation, with more time wasted. And perhaps hold off on the “hookups” until you are convinced you like what you see with a potential suitor.

Do the work upfront. Explore thyself. Know thyself. Love thyself. Companion thyself.

And when he does come along? Well, it’s likely to be messy (as all relationships are) but it’ll be a much happier messy of your choosing – grounded in a proper vetting of compatibility – not one that feels like a settling or selling of your soul.

And if one comes along, but doesn’t work out even after better judgement calls are made and compatibility checks are complete? Well, you’ll have a powerful companion within yourself to retreat to, heal with, and recover so much quicker…


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