confidence, dating, men's issues, personal development

Four Mistakes Men Make Before the Third Date

It’s happened to all of us: you’re getting to know a woman, and you both seem to be hitting it off. Maybe that first date is some stimulating, shared outing; the second date, something more quiet and conversational. But by the third date, whatever it is, something fizzles. Suddenly you realize that she’s not the catch you thought she was; or she’s visibly turned off by something you didn’t even know you were doing. Or worse, you think it’s gone really well – but you don’t hear back from her. Or she sends you a polite note saying thanks, but you’re not for her.

A young  loving  couple hugging and kissing on the beach at suns

If you’ve spent a lot of time giving and receiving dating advice, as I have, you know that it’s dangerous to overthink any single interaction. Every situation, and every woman, is different, and each early interconnection has its own trajectory that includes a feminine person, a masculine person, the dating environment, logistics, and our inner lives. There are too many variables to look at in any meaningful way, and in any case, it’s best not to ascribe motives to a woman that she hasn’t verbalized to you herself.

But there are some common pitfalls. They’re easy to avoid if you’re careful; if you know how to relax; and if you can communicate well and circulate your desire through your body. (If you don’t know how to do these things, get in touch with me.) For these tips to be effective, you need to know what (and who) you’re looking for.  You also need to demonstrate that knowledge through your every word and action; be in touch with your own feelings and desires, and be honest with yourself about them.

Mistake #1.  Showing continued interest when you’re no longer interested. Why do we men do this? Maybe we’re acting out of fear and scarcity and want to “lock in” what we have; maybe we’re not sure what we’re looking for; or maybe we’re planning to keep her on the sidelines for NSA sex. In all cases, you’ve already decided she’s not what you want, but you find yourself making plans with her anyway. You continue to text her, you flirt with her, maybe you even go on another date or two.

It’s often worth sticking around for a while to find out if your feelings for her change. People can, and do, find the love of their lives in someone who “isn’t my type” or who made a bad first impression. If there is only one aspect of her you find unappealing, and everything else looks good, it’s wise to be patient with yourself, and with her. But if you find the thought of calling her again exhausting; if you’re easily bored this early in the interconnection and have to constantly resist the urge to look at your phone or at other women in the room; or if (yes, this needs to be said) she absolutely disgusts you, you need to break it off – early and cleanly. To do anything else is a disservice to her and to yourself. These are not the same rules that govern a long-term relationship. In a committed relationship, there are going to be moments when we find our partners exhausting, boring, or disgusting, and our job, as loving partners, is to love our women through their least attractive moments. But the relationships that survive these moments are those grounded in deep physical and emotional connection. If it isn’t there from the beginning, you won’t be doing either of you any favors by continuing to stay with her. It’s better to be alone than with the wrong person. (Women understand this, by the way, better than we do, in recent years.)

Know your desire. Get acquainted with what it feels like in your body, and in your heart. Trust your deepest wisdom. If you’re still not sure, talk to your friends.

Mistake #2. Being too nice. It’s fine to give her a compliment – once. But if you continue to do so, she may think you’re being too nice, and if it continues past a certain point, she might actually stop believing you.

Recent research suggests that being a jerk, counterintuitively, can get results. High disagreeableness correlates with a wider variety of sexual partners, and the correlation cuts across all demographic and socioeconomic groups. But the same women who select men for casual sex select different men for long-term relationships, and those men tend to be kinder and more sensitive. Bottom line:  if you’re a nice guy looking for a casual fling, you might need to cultivate some qualities, such as social dominance and insensitivity, that don’t come naturally to you, and if you’re a disagreeable man looking for a long-term relationship, you need to blunt your edges.

Don’t be afraid to give her a sincere compliment about something you notice about her. Choose one aspect of her, preferably some choice she’s made, an accessory or an article of clothing, rather than some aspect of her face or body, and deliver your compliment sincerely and with good eye-contact. Let her hear it, and see how it lands. How she handles a well-delivered compliment will tell you a lot about her.

Being too generous is part of this “too-nice” quality. Spending more money than you usually do on a night out will be picked up as low-value behavior, and will actually decrease your chances of another date. Don’t take a cab if you normally take the subway; don’t take her to a five-star restaurant if you’d normally go for pizza. Although, for some women, high income communicates high status and marriageability, if it isn’t genuine, the outcome will be worse. You may think you can fake it, but trust me, she will know if you’re using payment methods you’re not used to, or negotiating wine lists you don’t know anything about. Even if she feels special to you, demonstrating it by being overly generous will lead her to expect such treatment all the time. Can your wallet handle it?

Mistake #3:  Not touching her. The topic of kino and physical escalation is a controversial one, but I’ll say it directly:  from the first interaction, you need to be touching her, at least in social ways if not romantically or seductively. Even during a chat between friends, there’s a physical conversation happening, or not, that sets the tone for the entire interconnection. It’s worth paying attention to what’s socially acceptable in her culture; some societies value touching more than others. But by date #3, an interconnection is defined, in large part, by how two people are handling each other physically. (And recent studies show that physical touch has social benefits that go way beyond sex and romance, but that’s a topic for another article.)

Physical touch is how you separate yourself from her other friends and establish yourself as a potential intimate partner. Elbows and shoulders are usually good starting points for social touch. As emotional intimacy develops, a man can move on to the hands, hair, and the small of her back. Keep alert to her responses, and calibrate accordingly. If she asks you not to touch her, don’t! She should eventually be reciprocating.

Mistake #4.  Giving information instead of emotion.  Information and small-talk are instant killers of romance. “What do you do?” “Where are you from?” Do you really want to ask these questions, or answer them? Women (and, much of the time, men too) want to be taken on an emotional journey. They remember and value feelings, rather than data. Tell stories she’ll remember, give her impressions of textures, sights, aromas. Your own feelings are a great guide here. If you’re bored, chances are that she is too. If you’re relaxed and having a good time, she likely is as well. It’s probably better to be a bit of a jerk than to be boring on a first, second, or third date. Don’t be afraid to voice your strong opinions on wine, music, or politics. Ask her for her opinions too, and playfully challenge them if she sounds too deferential or accommodating.

You can talk about the weather, if the talk reflects your true passions and experiences. But too often, small-talk and information are used as a way to hide – either because we’re shy, or because we’re afraid to make a mistake or to let the woman see us as we are.

Avoiding these mistakes are a good start to getting what you want in the world of dating. Knowing what you want can set the tone for the interconnection. You’ll be able to communicate your desires clearly and, if a connection isn’t what you’re looking for, you’ll be able to break it quickly and honorably. Taking your date on an emotional journey, touching her affectionately, and avoiding insincerity will show her who you really are. And who we are is what we should always aim to be to women. After all, why would we want to be anyone else?


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