Romance is a fascinating thing, if you think about it. But it’s also rather bizarre. Like it or not, I end up attracted to people who would make terrible partners, and I sometimes find myself completely unmoved by someone who, by all accounts, would make a great match for me.
It’s for this reason that I’ve decided to be a bit more discerning about whom I spend my precious late twenties pursuing, right from the beginning. From what I can tell, I’m not alone in that, either. There's something about that big looming three-zero that makes you want to be a little bit more intentional about your life, dating especially.
So if you’re wondering what in the world is going on inside your date’s head, want a little inside information as to how to put your best foot forward, or simply want to be entertained by the musings of a wandering bachelor, keep reading. Without further ado, here are 11 things I want to know about a woman I am attracted to right away.
01. IS SHE AVAILABLE?
Sounds simple enough, right? Of course, I want to respect the boundaries in place if she’s in a committed relationship. But, beyond that, there seems to be a whole spectrum of how available a woman really is making herself, even if she can’t necessarily claim to be spoken for, if you will. It’s to the point where I’ll even flat-out ask, as clearly as possible, “Are you looking to enter into a relationship with somebody?” Believe me, it’s nice to be able to clear that up right away.
So please do tell us if you have anything you need to deal with before you’re ready to move on with someone else. But also feel free to let us know you are available. And don’t be afraid to be a bit forward about it, because we’re not always very good at picking up subtleties, if you haven’t found out already.
02. IS SHE CRAZY?
Hate to break it to you, ladies, but this one is definitely on our minds. And, just so we’re clear, we know you all are going to be a little crazy—as in, we have no idea how to predict female behavior—and some more (or less) than others. That being said, we need to know how much crazy we’re talking here. Is she going to get puking-in-your-bathroom drunk on your first date? Is she going to be giving out her number to my friends? Are beef jerky and Red Bull her idea of breakfast? Then we’re probably talking too crazy. Luckily, in my experience at least, the craziest ones can’t help but show their cards as soon as possible.
03. IS SHE INTO IT?
I don’t want to waste anybody else’s time, and I certainly don’t want to waste mine. So I’m on the lookout for cues that give me an idea if she’s engaged and interested. Simple things like if she’s late for a date, or even if she asks to reschedule, could be fairly innocuous. But it can also mean she’s not making me a priority or, worse, that she’s finding ways to avoid me. If she’s making a point to explain those instances and apologize, no big deal. If not, I might start wondering.
04. IS SHE FUN?
Life is serious enough, and a long-term relationship will have plenty of trials and tough times. It’s important to me that a woman doesn’t take herself too seriously and can see the lighter side of things. She can make fun of herself and she can make fun of me, and not necessarily in that order.
05. DOES SHE ROOT FOR THE GOOD GUYS?
Good: Twins, Vikings, Timberwolves, Wild, Gophers. Bad: Packers, Yankees, Red Sox, Badgers, Blackhawks, Patriots, Seahawks, Bears, White Sox, Hawkeyes… I could go on.
06. IS SHE KIND?
How much does she care about other people, and how does she treat them? How would she treat me if we were in a relationship? There are few things more important to me than discovering if she can treat people with kindness and how often she chooses to do so. Generosity, thoughtfulness, tenderness, compassion, empathy—basically I’m looking for indications that she knows she’s not the center of the universe and she prefers it that way. Kindness is rarely broadcasted, so much of it comes from observing the way she treats those around her. But a kind person typically has a hard time speaking any other way.
07. WHAT ARE HER VALUES, MORALS, AND BOUNDARIES?
One of the most impressive things I’ve noticed about certain women is when they’re able to draw a line in the sand on a difficult subject. What does she value enough that she’s willing to protect? What are her limits when it comes to what she’s willing to put up with? I do really stupid things sometimes, and I say really stupid things a lot of the time. Can she call me out on my bull? Can she say no to something when necessary, even when it’s difficult to do so? Is she sure enough of herself to stand for what she knows is right?
08. WHAT IS SHE ABOUT?
To ask a woman right away, point blank, about her deepest desires, hopes, and dreams can be a bit overwhelming. But I do want to know what gets her up in the morning. Finding out what is important in her life will tell me more about her than just about anything else. Whether we realize it or not, the way we live reveals what we care about the most. I’ve covered this one before, but ideally, casual conversation about how she spends her time will reveal she is already dedicating herself to higher pursuits.
09. DOES SHE WANT A FAMILY?
Getting married and having a family is a goal for me. So if a woman I am attracted to is not on the same page, then we are going to have very different ideas about what a relationship would look like. It might be hard to discover this information upon first introduction, but it’s a question I would definitely want answered on a first date. Better to understand each others’ expectations, specifically for an end goal, as soon as possible before moving forward.
Of course, that can be a bit much to ask point-blank, especially on the first date. So I listen for clues. Does she speak positively about children? When she mentions her married friends, does she roll her eyes? If there’s an opportunity to ask naturally, I do.
10. WHICH RELATIONSHIPS ARE IMPORTANT TO HER?
Is she close with her family? Is she too close with her family? In whom does she confide? Who does she trust? Is there anybody I will be competing with for her time, her affections, or her loyalty?Yes, it’s important for her to have friends, even bestie bffs forever. But as Andy Samberg knows, sometimes that means we get the short end of the stick. Believe it or not, I am looking for an independent woman, and that means she is independent from her friends, her parents, job, and yes, even her pets. If she’s wondering how anybody could possibly replace her pug, we might have problems…
11. DOES SHE BRING THE BEST OUT OF ME?
Ultimately, I’m looking for more than just a companion in life, and even more than a passionate lover (although those are both on the list). What I’m looking for is someone who makes me feel the need to step up my game. Because, here’s the thing: I want to step up my game. Bachelorhood is great and all, but it’s way too comfortable. I want to be inspired to realize my greatest potential as a man. And not just for my own sake, I want to be my best for someone else. Certainly, this is something that will take some time to determine conclusively, but I will be looking for clues from the very start.
All of this said, so much of what makes me attracted to a woman is fairly mysterious, even to myself. If nothing else, take this list as a sort of olive branch from one man to womankind, to help you understand what at least one of us is thinking. Now, to return the favor, I wouldn’t mind getting a few tips from the female point of view...