The Top 3 Mistakes Men Make When Flirting with Women
Lots of men tell me they are confused and wary when it comes to flirting with women today.
“What if I come across as creepy?”
“What if I’m unjustly accused?”
I get it — flirting takes a lot of courage and resilience to rejection.
However, you can transform this experience.
And guess what? Being smart and nerdy is more of an asset than abs and a fortune, in my opinion.
Here are the top 3 mistakes men make when flirting with or dating women:
- Qualifying yourself instead of her
- Using techniques instead of skillful honesty
- Casting too wide a net
Let’s break these down.
1. Qualifying yourself rather than qualifying her
You’ll set yourself up for bad dating experiences if you, like many men I work with, spend 99% of your time worrying if you’re ‘good enough / rich enough / ripped enough’ — and no time considering if she actually meets YOUR standards.
If you come to flirting feeling centered in your self-worth and being measured in your approach, you’ll have women swooning. Self-confidence and good boundaries are hot.
Rather than wondering if you ‘measure up’ and waiting for her to determine that, practice cultivating your innate worthiness, and notice what she brings to the table.
Unfortunately, most dating advice matches people based on surface-level characteristics. However, you want to consider if she has the deeper qualities that truly ‘meet’ you and will enable you to build a solid foundation together — like kindness, self-awareness, emotional maturity, good communication skills, and openness to growth.
How do you develop the self-worth that allows you to do this? This can be a life-long inner journey, but as a simple place to start, I recommend having a practice of writing down 3 things you love about yourself every day. Also, ask your friends for their honest reflections.
Cultivating self-love rather than relentless self-criticism is one of the practices my male clients have the most resistance to — and I get it! When I was at MIT, I scoffed at the idea of being kind to myself. Only being tough on myself was going to get me through, I thought. I needed to push — and this only worsened during my PhD.
For men, the pressure can be even greater because of the need to be a ‘provider’.
Paradoxically, motivating yourself from self-love is more effective, however (that’s a whole article unto itself to write!).
It’s not about being egotistical or ‘better-than’, but about a sober acknowledgment of the gifts you do bring (while also being aware of where you’re a work-in-progress).
2. Using techniques instead of skillful honesty
If you just want notches on your belt, or you haven’t developed good self-worth yet, then ‘techniques’ might get you attention — but it won’t be the right attention.
Instead, one of the key practices I teach my clients is to ‘go meta’ — that is, to reveal what’s going on for you.
This is an incredibly courageous thing to do that also gives her permission to be real — and she will thank you for it.
(If she doesn’t, she’s not right for a deep, long-term, healthy partnership).
Don’t go to extremes with this, however — too often, men interpret this as collapsing into a sob story.
No. Hold your center and your self-worth — but reveal a piece of yourself you might otherwise not.
For example, if she’s so gorgeous and you have momentarily lost your train of thought, say that!
“Actually, my mind is blanking right now — I was sincerely distracted by your beauty.”
Or, if you’re really wanting to get closer or maybe kiss her, but you’re not sure what to do, you can say: “Can I kiss you?”
Once when I was out on a 3rd date with a new man, we were having a really great, connecting dinner — and I knew we’d probably kiss afterwards, but I was nervous.
How could I give him a sign? What might he do? Would it be awkward?
Instead, on the way back to the car, he simply asked me “Can I kiss you?”
What a relief! I smiled and said an enthusiastic ‘YES.’
3. Not being specific about what you want
By far the most common mistake I see men making is being vague on their dating profiles. “I like hiking,” “I have a dog,” “I like sports”.
These don’t tell women anything about your inner world. They don’t show self-awareness, boldness, or vulnerability. They don’t reveal your dreams, fears, or desires.
Women want deep connection and relationality — and it’s hard to connect with surface-level generalities.
I get it, it can be vulnerable to put yourself out there. And I also know that men do this to cast as wide a net as possible, rather than narrowing the number of matches.
And yet, time and time again my clients have found themselves wasting time on ill-matched dates and sweating through interminable dinners, wondering when to ask her if she would be into, for example, dom/sub play — because they didn’t put it on their profile.
One man was getting inundated with women looking for an LTR even though his wife had died and he wasn’t ready for that yet. But he had failed to be clear about what he was available for on his profile.
Once he specified that he wanted something casual, maybe being a secondary partner to an established relationship, he immediately found awesome women who perfectly matched his interest — and he had fantastic dates that developed into the intimacy he desired.
The point is, if you have a non-negotiable, like not wanting to have sex before marriage, coming out as a sensual dom, or not wanting a primary partnership, put it out there.
Be you and your original, quirky self.
Will it reduce the number of matches? Yes.
Will it save you time and headache? Yes.
Will it make it easier to match with a great woman? Absofuckinglutely.
As a bonus, there’s one last story I want to leave you with.
You see, many men today also make the mistake of not being clear and assertive enough — not taking the lead — in dating.
I get it, it’s confusing in this era of equality. You want to be respectful, not domineering.
However, there’s something irresistible about a man who isn’t afraid to make a specific invitation.
For example:
Once, with a new man I was dating, we were texting about what we each liked when it came to dinner and drinks. He gave me a couple options in the area to choose from. They both seemed fine to me, so I said “You pick! Take me somewhere.”
But instead of writing back with a confident, clear response — “Excellent! I’ll take us somewhere great. Be ready at 7” — he continued to hem and haw and be indecisive, asking me what I wanted — even though I had just stated what I wanted!
It was a total turnoff.
On the other hand, the man who became my partner texted me this before our first date: “What are your dietary restrictions?” Once I told him, he said “Be ready at 7, I’m picking you up. Wear something nice.”
And we’ve been inseparable ever since.
Not all women are the same, and not all are like me — some might not like that level of polarity play. The point is: decide the kind of woman you want to attract, and then consider: what kind of invitation from you would turn her on?
The through-line in all of this is: skillful dating means cultivating your own self-worth, honesty, and assertiveness. Give yourself the gift of knowing that it’s okay to be you.
It’s something a lot of ‘Nice Guys’ and powerful nerds struggle with — and I love working with you on this.
I can tell you from my decade of experience in women’s groups that women are looking for powerful, relational men with heart.
Dating is just as stressful and weird for us, too.
Women actually want you to succeed.
Keep that close to your heart.
If you want more on how to up-level your inner game when it comes to dating…
Get my Free Dating Guide for Smart Men.
Stop unwittingly repelling the very women you want to attract and get free from repeating patterns in dating.
Download 10 Ways to Meet Awesome Women — OFFLINE here and attract gorgeous AND emotionally-mature women who you’re actually attracted to!
Dr. Jessica
xo
