[This article was included in my print newsletter, and is reprinted here with a word that some considered vulgar).

I remember my first encounter when a relationship blew up; I was hanging out with a guy who was dating what I considered a fantastic gal (beautiful, smart, and usually funny), and she happened to be there. I must have been 17, and we were at a local pub where I was admittedly underage. He’s a Brit, she’s American.

The girl was obnoxiously drunk, but my friend had maybe two pints in him over 4 hours. We were at the pub to watch some professional game of some kind, and him and I happened to work in the same consulting industry, so he invited me to the game. She tagged along because she was insecure of him being at a bar with the boys for some reason.

After 4 hours, she wanted to leave. Before we all met, he told me that she’s the type that wants to be dragged along, and if it isn’t what she wants to do, she’ll throw a hissy-fit about it. I appreciated the guy’s openness about his girlfriend, because most of his guy friends did think of her as perfection from afar (and that’s a subject that I will definitely dive into later). I still appreciate openness with other guys who are open about the downsides of their relationships (not just with women). I’m one of them now, and I have no fear to let others know when I’m not happy and why. Reputation comes from that sort of honesty.

So after watching her pull on his hand, then his arm, and finally on his shoulder to leave, the Brit said something that I can never forget and that stuck this day into my head for the rest of my life: “Don’t piss on my good time.” The next words were either “Take a cab,” or “I’ll have the bar get you a cab.” That was it. I was floored. I grew up in a fairly “everyone is equal” family, and probably 50% of my friends till then were women. I was pretty angry that he didn’t want to leave, and I felt that he had slighted her and was in the wrong.

Years later, I’ve changed my tune completely. Relationships of mine that were stable and fun had a priority I didn’t necessarily notice: a woman’s respect for my time with friends, or alone, or doing something I like to do. The girlfriends I had that really made me frustrated, depressed, angry and distant were the ones who did exactly what my Brit friend told his girlfriend not to do: they ruined my good time.

Women’s insecurities are very hard for men to deal with. They just don’t know how to approach an insecure woman that has other great traits, but is so insecure that he won’t let him be him, won’t let him be away from her for an evening (or a weekend, let alone a week). It’s a terrible situation to be in, and if the signs are there in the beginning of a relationship, I generally tell the guy (when asked) to hit the road. You can patch a punctured tire, you can’t fix a shredded one.

Of all the men in my life (casual acquaintances, close friends, family, and those who e-mail me for help), the ones who are unhappy in their relationships can be pegged almost 50% of the time to being with a woman who won’t let them have a good time. I’ve spoken to unhappy men, generally a new one every few days, and I always ask them the same first question: “When was the last time you had a good time?” If the answer is “I can’t remember,” then I ask them: “When was the last time you went out without your girlfriend/wife?” If I ask the second question, the second answer is always “I can’t remember.” Bingo.

I’m not saying that you shouldn’t go out regularly with the woman you love. What I am saying is that you have to ascertain her comfort level if you do try to go out alone, with friends, or take a trip. I’ve stopped counting how many men have ignored this advice, and have suffered the consequences. I’ve also stopped counting how many men HAVE taken this advice and have thanked me less than a week after ditching the relationship.

Signs that she won’t let you have a good time:

1. Jealousy when you want to go somewhere without her. This can start with “Who’s going to be there?” (which is fine) but continues with “Who else?” This is a loaded question, and there is no good answer. One answer is enough, even if it is “Just the guys.” If a question is posed as “Are any girls going to be there?” she’s the type that’s going to ruin any fun you may have in the future.

2. Outrage that she’s not invited. I usually recommend bringing a new girlfriend to guy’s events at least once, to see how she reacts. I’ve met some amazing gals who do great when tagging along with their boyfriends. Focus on the word some. I’ve also met a great many who should never be invited again — they’re just not happy being there, so they want to steal the focus to them. If you’ve tried to integrate your lady into a guy’s night (or weekend or trip), and she hated it but still wants to come, you’re going to have to deal with that outrage forever. There are going to be things you want to do in the future that she will not want to do, but she won’t let you do them.

3. She won’t leave you alone when you do go out. You know the guy: his cell phone is beeping every 10 minutes, and it’s his girlfriend. This isn’t jealousy, this is pure insecurity, and it is a sign that the relationship won’t work out. I’ve never been wrong about this one. My advice: if you get 2 text messages from your gal in 30 minutes, turn the phone off. There won’t be any emergencies, problems, or needs while you’re out. The relationship at that point is probably ruined, but it’s going there anyway.

4. She wants every detail about when you did go out. “Who did you talk to?” “Who else?” “What did you eat/drink/watch?” It’s great to have a gal who is interested in your life, so please don’t think I am against sharing. The difference between the great inquisitive girl and the horrible inquisitive freak is the times they inquire to your life. Does she ONLY inquire about your “day” when you’re out doing something fun? If she never asks about work, the time you spend with your family, the work you did on the lawn or cleaning the garage, then she’s the freak. I personally love an inquisitive woman who just wants to know how my day has gone; I don’t want the rubber hoses coming out only on the occasion that I happened to be out doing something fun.

5. She tries to come up with a better plan. You want to go to watch a game with friends, or you were invited to an office party, but she finds something else to do: a concert, a movie, dinner, whatever. Women who can’t understand that a man can have fun without them often times come up with things to do that can be fun for both of them. I’ve had a standard answer to this one: “That sounds like fun, why don’t you do that while I’m out?” If she can’t handle that idea, run. If she sits on the couch all night, staring at the clock, run.

6. She’s obsessed with your exact schedule. “When exactly will you be home?” “Where exactly are you going?” This is a pre-event leading to disaster. It’s fine to be a bit obsessive-compulsive about details, but not if they’re only obsessed with the time you’re away from them.

Most of the women who were on receiving ends of my advice to men regarding having a good time have disagreed. But I’ve met some of those dumped girls again, and they’re reigning the same terror on their current men, usually husbands. It’s a terrible life to live, a marriage where you’re not free to have fun. I truly believe that the day comes early where the signs are visible that your gal is either going to be great, or terrible. Watch those signs, and make the proper changes to your relationship if you fear a future that is only about her, and never about you.

Zion, IL
By A.B. Dada
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In the past 4 weeks, I’ve had not one, not two, not even three but four guy friends “challenge” me with trying to find a solution with a common problem they’re all having: how to deal with the insecurities of their girlfriends (not wives, not fiances). Most of the guys have been dating the ladies for 4-6 months, and all of them have the exact same concen: their girlfriend is jealous, fearful, badgering, controlling, and over-inquisitive of what the guys are doing when they aren’t with them.

One friend is self employed, so his schedule is definitely odd at times. Another friend is unemployed, but doesn’t like to be home all the time with his girlfriend (who doesn’t work, and doesn’t have a huge house or kids to take care of). The third friend is a client, and he’s going crazy because his girlfriend was fine during tax season (he’s a CPA, and was overwhelmed) but is now “acting crazy” during his slower season. The last is just a guy I’ve spoken with at a pub from time to time, who came across me by searching Google for “dealing with insecurities.” Amazing that he also knew me in real life. His girlfriend hates that he manages a bar and grill.

I asked all of them the same thing: how much of your past did you share with your new girlfriend? What did you tell them about previous loves, crushes, relationships or friends? All of the guys shared with me the following: they told them too much.

Insecurities in women are tough to deal with — we live in a society that champions the idea of women being equal, but this puts many women at a disadvantage because NO ONE is equal, and it makes women feel like they must live up to this idea of being a strong-willed, independent, self-capable person. When a person is led to believe that they are the weakest of a group, their lives are negatively affected by what I consider a terrible lie. It is no different to me than what many of my friends were led to believe about housing: prices always go up (they don’t). Almost all of my renting friends made the terrible mistake of buying a home when they weren’t capable of handling the cost and maintenance. Again, people were lied to that they were lesser people because they were renting, and now they made bigger mistakes believing that. I see no difference in how society lies to women about telling them they can be equal to all other women, and men. This is a force that causes a great deal of insecurity in many women.

A trigger for a woman’s insecurities can come directly from a man offering her any sort of information about him that might connect him to men who have treated her badly in the past: fathers, brothers, uncles, boyfriends, bosses, whatever. Tell an insecure female you have been in love before, and she might start wondering why you left that previous love, and if you’ll leave her. Tell an insecure female that you had casual sexual relationships before, and she might start wondering if you’re with her for the same reason. Sidenote: Insecurities in men are no different, but that’s not the point of this article.

It has always been my rule and goal to limit what you share with your girlfriend early in a relationship. The less you offer about your past, the more intrigued she will be, increasing her interest in you, and wanting to know more. But there are some things you just can’t share, ever. Many people believe that men are visually stimulated, and women are emotionally stimulated, but this is not a fact by any means. In my experiences, women are the visually stimulated ones (look at the makeup, clothing, and accessories!) and men tend to be more logically-associated. Again, this has been my experience.

I queried my 4 friends about what they may have shared from the past that put their girlfriends on the defense. Here are the questions I asked, in no particular order or to a particular person:

1. Did you ever tell her you were in love with another woman in the past? Some women will ask this question. My answer has always been “I’ve had crushes, and I’ve had what I thought was love, but after digging deeper we mutually realized that things weren’t heading in a direction we both shared.” It’s always the truth, but it doesn’t put pictures in her head. Relationships that end should be always on a mutual understanding of a lack of direction, not a lack of passion, love, friendship or sex.

2. Did you ever tell her you had a relationship with someone at work? That’s a common question. My answer has always been “I’ve gone out with people I’ve worked with, but I was young and didn’t realize how much it affects work. Nothing serious, but definitely a learning lesson just to keep business and pleasure apart.” Again, this shows you are a logical and concerned boyfriend, not someone who was sleeping through the entire Human Resources department.

3. Did you ever tell her you hooked up with someone? I can’t believe guys would answer this question in detail, even if you’re a virgin till marriage, “hooking up” creates some rough mental pictures. Even if you HAVE “hooked up” with someone before, the best answer is “I’m not one to jump into a relationship of any sort without getting to know the person much better.” This isn’t a lie, because if you did hook up, you made that decision based on knowing the person “better” than not at all. If you tend to hook up with people without saying 5 words to them, you probably aren’t ready to be in a long term relationship until you overcome those desires.

4. Did you ever tell you you’ve kissed a friend, and called it a mistake? I’ve fielded this question before (I had a lot of female pals when I was younger), and I am shocked at the amount of guys who admit to this. The moment you cross that line, the woman will never trust casual female acquaintances in your life. My answer has been “I’ve never kissed a friend, but I’ve had past crushes that turned into friendships when it was obvious things weren’t heading in the same direction.” No one kisses “just a friend,” there is almost always some attraction that is more akin to a crush than a friendship. Don’t make a friend into a crush, make a crush into a friend. Cap it off with “Nothing happened after we realized we really didn’t like each other that way.”

Insecurities in women come from a bad past, usually. Old drama turns into modern baggage, and it is hard to deal with once you start stuffing your own history into her baggage. If you’re going to open your mouth too much, think the mental picture through that might come from what you say. Limiting yourself to being logical, instead of visual, can lead you to a healthy relationship that helps the insecure woman grow, rather than stay on the course of distrust and jealousy.

Lastly, if it is obvious that she is too controlling, too jealous, and too insecure, you should realize that those things don’t change. Once her insecurities enter your relationship, they can be a terrible weapon against stability in the long term. I’ve dated some nice and brilliant women in my life, but some of them had insecurities that were impossible to tackle. I don’t have sympathy for the guys that married them, figuring they could change the women, only to make all the mistakes I listed above.