I've been dating a girl off and on for the past 2 years. When I originally met her, I was overweight and on a dry spell. She was very attractive, genuine, and truly enjoyed being around me. I became enamored of her and fell in love for the first time in my life. Prior to that, I was accustomed to having sex with 20-30 women per year and living the completely uncommitted lifestyle.

Personality-wise, we are quite different. I am sarcastic, quick-witted, and very logical when it comes to decision-making in my life. She is kindhearted, a bit gullible, and tends to make decisions based on her emotions. Although we can share a laugh at times, I often feel like we're not on the same page in conversations.

We also have drastically different incomes. I make six figures and she has been a student for nearly the entire time with minimal income. She is not high-maintenance and she's generous with the money she has, but I would like to take trips and do other activities and it just rubs me the wrong way when I'm paying for every flight, hotel room, meal, and entertainment activity. She will likely make good income in the long run due to her education, but it's difficult now.

The sex is great. I usually get bored quickly with the same girl, but I'm still very turned on by her. It is still not as exciting as multiple partners, though.

Beyond the first three months, my love for her started to fade and she fell deeply in love with me. I got in better shape and began to receive more interest from other attractive girls. I wanted to be committed to her, but it was difficult to change my lifestyle. I began to feel smothered by the way she wanted me to show more commitment and frequently tell her that I loved her when I wasn't even sure how I felt.

Ever since then, we've been on the same cycle. Things will be smooth and the sex will be good, but then she begins to ask questions about where we stand. I tell her that I'm not ready for a serious, committed relationship at this time and she gets angry, says that we should just stop seeing one another, and breaks communication for a week or two. Most of the time, I just leave it alone and she eventually comes back.

I've still been sleeping with other girls from time to time, but I haven't found anyone who compares to her overall. I'm getting to the point in my life where I would not mind being with someone in a committed relationship, but when I've tried devoting myself to her completely, I get very bored and realize that we have different personalities. But, when we do separate for periods of time, I feel like I've made a mistake and will regret losing her if it ever happens permanently.

Any advice on this? Do I need to just get over the initial feeling of loneliness after a separation to be able to see that this will never be functional? Or, do I need to realize that a committed relationship is going to feel like this with any female?

I think this might be the only way to actually maintain a relationship these days, man.

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The ultimate lesson of psychoanalysis is that human life is never "just life": we are possessed by the strange drive to enjoy life in excess, attached to a surplus which derails the ordinary run of things.
-Slavoj Zizek

Speaking as a guy who has been teaching pickup for 6 years, and has been in a relationship for 5 years.. I'll give some advice from my experience.

1) Being in a relationship when you are clearly able to get lots of girls is interesting, but I love it. I stayed single until I found someone I really really clicked with, who completely understood me. She's on my wavelength completely. Because of my work,I'm faced with temptation multiple times every week. Only sometimes is it really difficult not to do anything about it, most of the time it's just 'another chick'. It doesn't sound like this chick is the winner for you at any rate. My guess would be you are hanging int there because shes a really nice girl, and part of you doesn't want to hurt her either. Doing that ultimately just degrades your self-esteem and wastes both of your time.

2) Be wary that you aren't using women as a drug like any other. The high from picking up women is almost chemically indistinguishable from drugs like cocaine and heroine. If you have deep seeded insecurities or unhappiness buried somewhere, some people use food, some people use alcohol, some weed, and some use women. That doesn't mean you disrespect the women in the process, but for you, picking up women is plugging an insecurity which you really need to deal with. If you don't, you'll forever be romantically alone.

I hope the above two points give you something to consider.

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Damien D
Head Coach - The School of Attraction
The School of Attraction

I was guilty of #2 in the past. I did not lose my virginity until my early 20's and I ended up having sex with over 100 girls over the course of my mid 20's. Many were not very attractive, but I felt self-confident and handsome after I managed to get any girl to have sex with me. My impetus for sex was often just to brag to friends or to feel proud that I pulled something off. I feel like I'm beyond this now. I'm much more selective with who I talk to and I only have sex with girls if I'm very turned on by them and find it difficult to resist.

I think you may be correct on #1. It's just difficult for a few reasons. Although she's the epitome of the good girl and I find her to be a bit boring, childish, and not challenging in many conversations, I worry that I won't be able to replace her. It's difficult to find a girl without children or other baggage who is attractive, faithful, and genuinely in love with you and nobody else. She also represents where I'm trying to go with my life. She is motivated, focused on her education, and never goes out getting drunk or partying every weekend like many of the single girls I meet. I was guilty of that for years and I'm trying to step away from that lifestyle and focus on pursuits that benefit my career, education, and well-being.

On the other hand, I wonder if low self-esteem is causing me to settle for what's guaranteed and not take risks with my love life. I've been putting off commitment with her for years in an attempt to bide my time, but I don't feel any more confident in a relationship with her than I did before. It seems like my biggest fear of letting her go is that I'll eventually realize my mistake and she will be in a long-term relationship or married to someone who recognized her value.

Mate, I honestly know how hard it can be.... Prior to my current girlfriend, I was dating a girl who was perfect for me on paper in so many ways... She was a behavioural Psychologist, no children, very intelligent, kind, nurturing, loved me completely, looked after me, loyal etc. We never even had fights in 18 months.

But I got bored of her, and part of me felt guilty for it since she was such an amazing woman. I procrastinated for months about what to do...

But relationships are like that man, just because they are great logically doesn't mean anything if they don't "DO" it for you in the long term.

ALSO, there are a metric tonne of awesome women out there.. Don't be worried about that one. Sure there are plenty of women who aren't worth the effort, the world is flooded with them, but I'm coaching 2 nights a week every week, and at least 2x a month I meet a woman who I think is really awesome and totally worth dating. And I'm incredibly picky about who I would actually date.

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Damien D
Head Coach - The School of Attraction
The School of Attraction