3 Ways to Figure out Exactly What He's Thinking

Jenna Birch
Contributing Writer
(Photo: Getty Images)

Dating often seems really confusing to millennials … and it is. Never has there been a generation dealt with so many “options,” so many buzzwords (“ghosting” was just the beginning), or so many ways to miscommunicate.

One of the toughest parts of dating is that “being on the same page” is never a given. Women often date for a potential relationship — but they’re also often dating men who are socialized to play the field instead of settle down, and don’t have a biological clock to contend with. This can ultimately lead to romantic mayhem. You’re open to a relationship, meanwhile your date is just bored on a Thursday night, trying to get laid, looking to get over an ex with some new company, etc. The list of different intentions can go on and on.

The very essence of compatibility is figuring out if you’re looking for the same things. However, lots of women fail to take the appropriate steps to figure it out.

I’m not suggesting you show up to a first date asking whether the person wants to get married (in fact, please don’t). But I am suggesting you listen closely, don’t let connection blind you, and know what you’re comfortable with before you graduate into deeper levels of intimacy.

If you’re dating for a relationship, then you’re probably the person most invested in the outcome of every date and every prospect. With that, there are a few tactics I want you to employ as you meet up with your potential future plus-ones.

Watch his language.

Most men tell you everything you need to know about them. If a guy’s not looking for a real relationship, or even open to one, here’s the best news ever: He will tell you. Is he going to say the words directly? Nope, probably not. But he will still tell you.

Guys who aren’t looking for a relationship will present those barriers to you. “It’s a really busy time right now,” “my career is taking a lot out of me,” “I just got out of a relationship,” or “I’m applying to grad programs” are cues that they’ve got other stuff on their plates.

Likewise, guys will hint at their history. I’ve been on many dates where men have professed to leave a bunch of women’s hearts in their wake (whoa). Watch for them to slide their flaws into their speech. “I’ve never been great at commitment,” “My communication skills aren’t great,” or “My exes are all crazy” are indeed forewarnings. If he was really concerned about scaring you off, he’d probably not say such things. He’s setting an expectation: Don’t expect this to end well.

The major problem with dating for a relationship is that you are blinded by connection and chemistry, because that’s what you’re looking for first. In the presence of sparks, you may tend to brush off comments you should consider — literally everything just shy of, “I’m bad news, sweetheart” — and start projecting your hopes and wishes onto a prospect you really like. However, if you only took a teensy step back, you could see the whole situation for what it is: Risky, and probably not what you want long-term.

So, listen to his words. Be discerning. One red flag is normal; we’ve all got baggage, we’ve all said some questionable things. A bunch of red flags is cause for concern. I would not tell a grown woman, “Don’t date him.” But I am definitely saying, “Date him with eyes wide open,” “he’s very possibly preoccupied,” and/or, “he doesn’t exactly have a good track record in relationships.”

Look for open signals.

Men (or women) aren’t necessarily always “looking” for a relationship. However, if someone is “open” to one, it’ll be obvious for one simple reason: They are putting their best foot forward, and they dont want to give you reason to question their motives.

A person who’s open should be self-aware enough to care about the implications. Staying in consistent touch shows he wants you to know he’s thinking about you. Planning dates in advance instead of last-minute shows he wants time in your schedule. Explaining himself shows he’s thinking of what might give you pause, like “Sorry I didn’t call at six; I got held up in a meeting” or, “I’ve been looking at grad programs out of state — unless, of course, I have reason to stay here.”

Remember the obvious: When we want to make a good impression on someone, we are aware of what might come off poorly and what we need to do to garner their good opinion. If a guy isn’t sending you positive signals through his actions, and giving you the appropriate explanations for mistakes or disappointments, he’s basically telling you that a relationship with you is not on his list of short-term priorities.

Anyone who is intentionally vague or evasive is playing you or doesn’t know what he wants at that very moment. Be aware of both possible scenarios, and understand that a general vibe of “openness” is the best kind of relationship material.

Be as direct as possible.

Everyone is afraid to ask the tough questions while dating — and I agree, you shouldn’t come to a first date with guns a-blazin’. You do not need to know what his five-year plan is, when his last relationship was, how he views commitment, or what he’s looking for in a life partner. (That’s the literal definition of a buzzkill.) Just have fun, while keeping your eyes and ears open for him to indirectly reveal crucial information.

At the same time, it’s important to recognize what your dating goals are and what you’re ultimately comfortable with (or not). Then, you need to lay out your boundary lines when the moment comes. We are a generation of mixed signals and poor communication, making direct questions all the more rare — but all the more necessary.

If you are ever in doubt about a person’s headspace or intentions, ask point-blank questions before forward movement is about to happen — or when you feel it should be happening, but isn’t. If you’re feeling antsy because you don’t know how a guy feels about the growing relationship, you need to ask, “Are we exclusive?” or, “Are you seeing other people?”

Likewise, before you sleep with a guy, you need to determine what you’re okay with ahead of time. If you want a relationship with the man in question, you need to say, “Do you see a relationship with me?” You could also use very direct statements like, “I don’t sleep with guys I’m not exclusive with,” or, “I don’t do casual.” (I lifted that last line from super-smart dating expert Susan Walsh.)

Bottom Line: Goals > Guy

When you’re looking for love, I want you to lose your fear of scaring off incompatible partners. To get what you ultimately want, independent from any one guy, you need to lay it out there when the right time comes. I’ve found men will evade, but usually dont lie. They’ll try to avoid confronting issues they’d rather not consider, but they will do so if you bring it up.

So, bring it up. It’s better to be honest with yourself and get the answers you need, rather than regret the time and emotion you spent on a person who was never compatible with your desires.

Jenna Birch is a journalist, dating coach, and author of The Love Gap (Grand Central Life & Style, January 2018). Her relationship column appears on Yahoo every Friday. To ask her a question, which may appear in an upcoming post, send an email to jen.birch@sbcglobal.net with YAHOO QUESTION in the subject line.