Is It Your Job To Soothe Her Insecurities? | Doc Love - Dating Advice For Men

Is It Your Job To Soothe Her Insecurities?


(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).

Hi Doc,

I’ve been a faithful reader of your columns for over three years now. I’ve tried to use your principles, especially being a Challenge, in my current relationship with June (we’ve been together for over two years), but it’s not working as well as I thought it would. There’s something wrong, but I don’t know what it is.

June and I met in our last year of college. We started dating after three weeks of getting to know each other as classmates. I used your techniques from the get-go and they worked! I appeared confident,
decisive, and didn’t always give in to June’s whims. I guess that’s how we’ve been able to stay together, and she even moved to Taiwan from her homeland (Hong Kong) for me.

But this is where things might have gone wrong. June is an incredibly insecure girl. Let me give you an example. On our first date, which was lunch, we were at a restaurant where some of the customers at other tables were being noisy. Therefore I decided that we should leave. However, she interpreted this to mean that I didn’t care about her and acted stone cold for the rest of the evening. When I asked her what was wrong, she wouldn’t say a word. Finally her friends intervened and resolved the situation.

Another example is that she’ll compare the movies and novels she reads with her life and concludes that a guy should do anything for the girl he loves. Doc, since this is her first relationship, all she can compare me to are the men from the movies and books she’s read. So if I don’t measure up well (in her mind) to the fictional guys, she becomes fearful that I don’t love her enough. Then she’ll try and catch my attention by acting really sad and angry, and I have to spend hours comforting her and reassuring her that I care a lot for her.

The problem is now worse, because June moved across the ocean to be with me, which means she has even higher expectations and demands from our relationship. The slightest imperfection or misunderstanding can cause her to worry and doubt the relationship. And since she is so insecure, she tries to save face by terminating the relationship first.

Whenever she pulls this tactic, however, she ends up crying and regretting what she said and did. Doc, I’m at wit’s end. How do I deal with such a sensitive and insecure girl? If I remain a Challenge, she’ll think I don’t compare with the romantic “wussies” from the Hollywood movies. Does being a Challenge work for a girl with low self-esteem and insecurities?


Mick - who got himself into a mess and doesn’t know how to get out


Hi Mick,

Before we get into the heart of your fix, I want to point something out. When you appear confident, it doesn’t matter what country the woman’s from, as you’ve demonstrated here. She can be from Mongolia or she can be from Montana, but all women, all over the world, want a confident, decisive guy.

Secondly, you mentioned that June wanted to do things that you didn’t. So how did you handle it? You compromised a little. You gave some ground to her, but to the rest of her demands you said NO. So I want to thank you for writing that sentence. Most guys would just read it and not give it a second thought, but there is a lot of power in it, and like Fast Eddie Love would say, “Dude, you showed that you have some real cojones.” Mick, there doesn’t have to be any guessing on your part about why you two stayed together. Your ability to take a stand and say NO is definitely the reason.


When a woman moves for you – in your case, across the South China Sea – that indicates high Interest Level. What you have to do is keep the Interest Level high – that’s the hard part. But at the same time, you have to have something to work with. And sadly, you don’t have that here. I’ll explain a little later.

When you left the restaurant, Mick, did you tell June why? Did you say, “Honey, let’s go find a place that’s a little more quiet?” Apparently you didn’t explain it to her, or she didn’t hear it. She pouted when you left, though, and that’s the most problematic thing here. This “mature” woman that you’re in love with acts like a seven-year-old. And like my cousin General Love says, “When they act like seven-year-olds and you live with them, that means they’re HIGH MAINTENANCE, baby!” And of course that means you have to put up with lots of stuff. Oh, it’ll be cute for a couple of months, but then you know what happens? It becomes a real drag.

Mick, if your girl has trouble confusing crappy entertainment with real life, you should be showing her Cary Grant films. When she wants to read, give her The Fountainhead by Ayn Rand so she can get to know Howard Roark. Between the two, she’ll get an idea of how a real man acts. What you’re telling me here is that if you don’t crawl around on your hands and knees and beg, and tell her everything is perfect all the time (when you’re really miserable) like the wussies in the movies and romance novels do, she can’t handle it. Sounds like your girl is in tune with reality, buddy!

Don't have a lot of time to watch a video from Doc but still want his great coaching?  Check out our YOUTUBE SHORTS

But wait a minute here, Mick. After you have the guts to stand up – at least some of the time -- to this girl, you then turn around and spend hours begging? You spend hours playing nursemaid? And you call yourself a Challenge when you’re down on your knees “reassuring” and “comforting” your unhappy princess? Is that what you’re telling me here, Mister Consistent Confidence? Get a grip, man!

So, she has even bigger expectations of your relationship? Tough! You don’t care about her expectations – and you’re not going to meet them. It’s time for her to grow up, or pack her bags and don’t let the door hit her in the you-know-what on her way out.

When June gets all insecure and sniveling and asks you where you’ve been, tell her “I’ve been out on a date with another woman.” If she bitches that she doesn’t like that kind of talk from you, you then say “Well, don’t bring it up, babe! It’s time for you to grow up. I’m sick and tired of you acting like a second-grader!”

And when she tosses a hissy fit and terminates the relationship, tell her “Honey, every time you leave you come back. Don’t you feel a little funny pulling that lame act, huh?”

Mick, what it boils down to is that this girl is a mess, and how she got her hooks into you I’ll never understand. Remember what I’ve told you guys again and again about making sure she’s clinically sane before you get involved. You’d be surprised how many girls out there aren’t. To you Psych majors, you have to be very, very careful from the get-go and not let her luscious bee-stung lips and legs that go on forever obscure what you’re really seeing.

Here’s how you deal with June. You sit her down and give her a talk. You tell her to grow up or shove off! It’s her problem if she compares you unfavorably with the romantic wussies on the silver screen. Because you’re not going to play along with it. You’re not going to cater to her. You’re going to do what’s right. Because like my Uncle Jethro Love puts it, ”Golly! You ain’t even got married yet! Once you tie that knot, it’s really going to be fun, boy!”

So the answer to your question, pal, is yes, using Challenge on June did work. It showed you that she’s no good for you. Challenge always works when it comes to women. ALWAYS.

Remember, guys: begging only lowers Interest Level.

Want Women To Look At You Differently (In A Good Way?)

Doc interviewed THOUSANDS of women - what he learned is taught to you - get THE SYSTEM/DATING DICTIONARY BELOW

About the Author