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Tag Archives: Dating

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My dear Jack, you’ve got to summon up courage to ask her out. You’re going to die in silence wishing for her if you don’t summon the courage to ask her out. Granted if she says no it’s going to hurt, and damage your pride a bit, but what if she says yes! You keep dancing around her, circling like a wagon in a Western B Movie, imagining all sorts of scenarios in your head. You’ve seen her going down the aisle with you, even seen her having a baby for you. You’re a couple in your dreams. But dreams don’t produce a wife. And all the desire in the world will not produce a marriage. Ask her out. If you don’t bite the bullet and ask her out, you’ll be friend-zoned. She’ll be the wife you never had. You don’t want to watch another man take her, do you? You’ll have regrets. Right now you’re like a sub on the sideline getting ready to come on the pitch as the referee is about to blow final whistle. If she says no, laugh over the whole thing with her. Make fun of yourself. Continue your life. What else are you going to do? And she may change her mind later – who knows these things! But if she doesn’t, you have your life to live. Seek another.

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My dear Jil, if a man won’t respect you, what are you doing in the relationship? This guy has no respect for you. He’s treating you like dirt, like he’s doing you a favour. You have a “take it or leave it” relationship, like he’s got so many options lined up and you’re just lucky to have him. How can someone you claim is your boyfriend treat you like a disposable? What kind of relationship is that? And you’re only confirming his opinion of you with your attitude to the relationship. You seem resigned. You’ve put yourself in a blackmail position. It’s why this guy has no sensitivity for your feelings. He sleeps with you, treats you like trash, talks anyhow to you, is insolent, crude, and you think you have a relationship. This guy has no regard for you. Continue reading

My dear Jil, when you’ve been on your own for so long, relationships can be difficult. Clearly, you can fend for yourself and you’ve been fending for yourself. You can take care of yourself. Being an executive, you’re used to funding your own travels, buying things for yourself, even taking care of others. So on a material basis, you really don’t need a man. Yet here you are wanting marriage. Means there’s something more you want. You’re also used to keeping your own time. You go to the gym according to your schedule, go to the salon on your schedule. You do social calls without need of informing anyone. You don’t have to give an excuse or render an explanation. So you’re pretty much independent and very independent-minded. Continue reading

Dear Jack, I think you should avoid the temptation of compulsive dating. I understand the loneliness thing. It’s nice to have someone you can call your own, someone you can go out with. There’s just that thing about showing up at a social event with a partner.

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My dear Jack, you’re going to hurt yourself trying to keep up with the Joneses. You’ve got to know your limitations in life, know the lifestyle you can afford and what you can’t afford. Don’t go and join a club you can’t afford for example. It’s not just about annual subscription, there’s a lifestyle attached. If you can’t afford a boat why join a boat club? It’s a minimum requirement not so? It’s not enough to buy the boat, you must also buy the lifestyle. There are administrative expenses attached to owning a boat. There’s parking fee and maintenance fee. You’re a young entrepreneur. Every penny you spend you have to make it by yourself. You can’t spend what’s not in the bank. The boat bill of a multinational corporation CEO is borne by the company. It’s part of the package. But you don’t have such a package. It’s why you can’t compare yourself to such people. And everyone at the boat club can tell you’re struggling to pay those club subscriptions. I mean how are you going to keep up the $50,000 subscription every year? Your business needs the money. It’s an annual subscription. How will you afford it? How are you going to sustain it?

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Dear Jack, I really don’t know how it would work, and my philosophy is, if it won’t work, don’t force it to work. Continue reading

My dear Jil, there’s such a thing as emotional stinginess. You can’t be emotionally stingy in your relationship. You want a boyfriend who fawns over you, telling you he loves you… But you deliberately hold back on reciprocation. You don’t want to be emotionally forthcoming, or even gracious, just so you’ll be in control of the relationship. It smacks of meanness, borders on coldness, manipulatedness and hardness. It’s a narcissus complex. If the guy adopts the same self-induced emotional constipation what do you think will happen?  Continue reading

My dear Jil,

You said there’s this colleague of yours who seems very much interested in you in the office. You’re wondering whether to get involved with him since you both work in the same office. Well let’s first clarify the office issue. Be sure your corporate policy allows for office romance. Especially since he is superordinate to you. He’s your senior in the office. That in itself can lay him open to charges of sexual harassment. But I don’t envisage you going after him with that, though emotions can be vicious when there are disappointments.  Continue reading

Relationship requires maturity. It’s why marriage is for men and not boys. Without maturity there will be emotional brickbats in a relationship. Such a relationship will trace the virtual paths of a yoyo. Up today, down tomorrow. Moods, temperament, anger, malice… these are pointers to the issue of emotional maturity in your relationship. And so because of a disagreement she withdraws to a corner and you become annoyed with the fact that she did. And so you withdraw in anger too. And soon it escalates as molehills are geologically blown out of proportion. Until everyone forgets the real issues. Now it’s all about pride and who’ll blink first. Such immaturity! Continue reading

My dear Jil, yeah I read your mail and was a little disturbed by a statement you made. You said, and I quote, “Bad guys get the good girls!” That’s a dangerous article of faith you’ve stated there and I do hope you don’t believe you’re fated for difficulties. And in any case, there are so many good girls who got good guys, and so many good girls getting good guys. Just as there are many good guys who got good girls, and many good guys getting good girls. By the very nature of statistics there will of course always be an anomaly. There will be some bad guys who get good girls. Just as there will be many bad girls who get good guys, but those are probabilistic issues not rules. And even if the anomaly becomes the rule you must be the exception. Continue reading

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