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Dating Columns Archives



Week of December 17, 2000


Dear Mrs Web,

I want to ask my girlfriend of four years to marry me. I have a ring and want to ask her Christmas Eve. We are both in our second year of college and I wonder if it is fair to tie her down all these years until we graduate? Am I wrong to ask her?

If you both are committed to each other, the two years will go by quickly and you will have a good foundation built for your marriage. In addition, in the fifties and sixties it was not unheard of for a couple to be married in college and helped through by both families. Visit my web page: Topics to Explore Before Marriage to help you both prepare for your marriage.

Dear Mrs Web,

I am a fifteen-year-old girl who has been dating a 16-year-old by for the past year. We keep dating and breaking up either because of the gossip around school (everybody talks about everybody) or because I meet someone new.

I have never kissed anyone in my life and he keeps trying to kiss me. I don't know what is wrong with me, but I donít want to. All my friends have all kissed someone. I like him and probably love him (if I knew what "love" meant). He says he "loves" me

Should I continue to date him?

As much as you like your boyfriend and are attracted to him; it sounds like you are not ready to settle down into a relationship yet. This is quite normal. You seem to have a level head on your shoulders, high standards, and do not want to get in over your head.

Being attracted to someone does not necessarily mean you should date him. The time has to be right. In many places, girls find it important to be attached to guys in order to fit in, and more than one who has written to me has told me she is unable to figure out what to think of, or how to feel or respond to her boyfriend. This is because she is nowhere near ready for the commitment and intensity of a relationship.


Dear Mrs. Web,

I am having an on-line romance with a wonderful and loving man. He has one problem. He is eighteen and I am 36. We have been corresponding for over one year. He is supportive, a dear and makes me happy.

Can the May/December relationship work between an older woman and a younger man? I care for him immensely and do not want to hurt him.

Should a mature, woman in her thirties be involved with an older adolescent boy? Frankly, May/Decembers rarely work out unless scads of money are involved. Then you are basically buying his company Ė and we all know what that is called.

Let us be serious here. Mature, deep, loving relationships require commitment, trust, compatibility, and a future. There isnít a future here. Young men need to commit to preparing themselves for their future and future responsibilities. He should be focusing in school, and building his personality and character at this time, not playing house with someone whom could be his mother.

You sound as if you want to love and commit to a man who loves you deeply and well. In my opinion, I think it is time to let this go and find someone closer to you in age, interests, and maturity.

Dear Mrs. Web,

I just received my birthday gift from my boyfriend. I was so embarrassed when I opened it. He gave me some things that are really sexual (clothing, books, cards) and I donít know what to do. We havenít been having sex or anything. Help!

Well, your boyfriend has certainly made his plans for your relationship clear. It almost sounds like he bought himself a birthday present.

He sounds crass and crude to me. I wouldnít waste anymore time on him. Lose him.

Dear Mrs. Web,

I have been attracted to a man for the past year. It has been obvious he has been attracted to me, and I had become very interested in him. I am surprised because I had always assumed he was homosexual. I needed to clear this up. We met for dinner at my request. I told him I was attracted to him. It turns out he is homosexual. He explained he found women in general and me in particular, attractive, and sexy. He said he enjoys womenís company.


He also denied he was aware of any attraction of any kind between us, but most of us know when someone is attracted to you by his actions. Did I misread his signals?


No, you probably did not misread him. Some people can only relate to others in the power/sexual way. Having others find them sexually attractive makes them feel powerful, wanted, and whole.

You were wise to find out his sexual tastes and back off. Some women just keep trying to win him over. That is a losing proposition because the issue is power instead of sexual or emotional attraction.




Week of December 10, 2000


Dear Mrs. Web,

I am a 28 year old male dating a 20 year old woman. Our relationship has been wonderful. She is leaving for a few weeks for an extended tour overseas. We are ending our relationship on a good note.


I have recently become fascinated with another woman. I do not want to distract myself from the last seconds of a beautiful relationship that is ending very soon. However, I can't shake my compelling attraction to the other woman. I don't know what to do.


You are in an enjoyable relationship with a woman. The relationship appears to have no commitments or future. It is entertaining for the moment. In addition, the relationship is ending.

An interesting distraction is in the wings.


It sounds like you would like to finish your relationship with your current emotional interest on her timetable. Therefore, you are looking at five weeks more of commitment. I think it is a superb exercise of character.


How? Well, you own your thoughts. You choose what you put in your mind and what you dwell on. You do not have to be ruled by your senses, desires, and emotions. This is how people stay in committed, lifelong, monogamous relationships. They backburner or round-file the things that get in the way of the commitment.


Dear Mrs Web,

I am embarrassed over my daughter. I have been dating a lovely
woman for about three years now. She is the nicest person I have
every known. My 30-year-old daughter says, "she's ugly". My daughter and former wife are obsessed with physical appearance. How do I deal with this?

The best defense against shallow and limited people is to require decent manners from them. Your daughter should be told it is never appropriate to talk about anyoneís appearance, except to praise him or her or express concern about their health. Anything else is tacky gossip. Sit down with her and make your expectations clear. The most unattractive women in this world are the rude ones.

Dear Mrs. Web,

Three weeks ago I went on a cruise with my mother. I met a man who works on the ship. He was our waiter. He swept me off my feet.

Since I have been home, he has either e-mailed me or called me daily. He says he is in love with me. He wants to purchase a cruise package for me so I will return to the ship. He also wants me to go home with him to his own country this spring. Should I pursue this?

You were on a cruise. Your waiter is inappropriately attentive. He is pressuring you with his interest. He even wants you to return to the ship, while he is working, with some sort of discount employee ticket. He also wants to take you home to Mother???

What do you know about him? Nothing. What do you get out of the relationship? Not much, I can see. What does he get out of the relationship? Hmmm.

Would I continue this relationship? No! Would I spend intimate time on a cruise ship with a man I didnít really know? No! Would I go to a foreign country with a man I didnít know? No! It sounds like he was trolling and you took the bait. There are men who prey on unattached women. They are charming. Thatís why it works. I would walk away from this immediately.

Dear Mrs. Web,

I am a 16-year-old guy who has been seeing a terrific girl for the past couple of months. We really love each other.

We talk on the phone every night for up to 4 hours. She really doesnít want to spend all her time with me. If we go out one night she just wants to stay home for the next few nights, not to do anything special, just not get together. I would really like to hang out together with her. Other couples at our school are with each other almost 24/7. I want that too.

Am I trying too hard? I need some advice.

Your girlfriend does not want to glue herself to you. This can be a healthy and mature sign. When an individual pursues her interests, and takes time for reflection she is deepening her personality.

Your friends who glue themselves to each other are not able to exist happily as whole single human beings. Since they have not overcome being "glued" to each other, they are more prone to making poor life choices to maintain "glued" status.

When looking for a mature guy, young women look for a man who can be devoted to her, have a successful life and a variety of interests and with an aim and plans for the future.

Cut back, find some additional interests, and work on being becoming the kind of adult you want to be. On my bookshelf page, I recommend Life on the Edge as one of the best books about the choices teens make that affect our future


Week of December 3, 2000


Dear Mrs Web,

I know a woman who is dating another guy. I want to know how to steal her away from her boyfriend. Can you tell me?

You can win a womanís hand by showing her your good heart, your warm, caring personality, your steadiness, loyalty and reliability; but most of all, by your honorable character.

Dear Mrs. Web;

I am a 24 years old single mother of a five year old boy. I want to marry and have more family. But I do not meet ANY men! I work with women as a nurse, all my friends are married. I very rarely have any free time. I am extremely lonely. 

My mother started her adult life as an unwed mother, friendless, and a nurse. She is now 56 and still unmarried. The last man she dated was my father. I am terrified of being like her

Sometimes, we copy the lives with which we are most familiar. It takes a real effort to get out of these tracks already before us. You have a double difficulty because you have a little guy who has claim on your time and heart.

One thing that worries me is that your fears about not ending up old and alone will push you into poor relationships. I am going to recommend that you think of some sort of individual/group therapy combo that will help you break your old patterns of relationships in healthy ways.

You sound like you are very alone in your life and this solution will bring a voice into your life that can help you change, find, and have a healthy, married relationship. I am not so worried about finding men at this time as I am about what you are going to do if you do find one.

Dear Mrs Web,

How important is attraction in a relationship?

Attraction to another either physically or emotionally is the force that initiates emotional intimacy. One would not want to be involved with someone who repels him.

Some people prefer living in neutral territory in their relationships. Even the ones they consider most intimate. I am not sure that deep emotional intimacy is attainable when one is in a gray fog of neutrality. Passion is an important part of any relationship and peopleís souls dry up and slowly die without it.

Dear Mrs. Web:

When I go to visit my boyfriendís family, they live in another state, I notice that the men order the women around and expect them to wait on them. It is not the life I want. It worries me. What should I do?

In some cultures and different socioeconomic groups, men are dominant in the family. If I were you, I would have some real frank talks with your beloved about his expectations and beliefs about a wifeís role in marriage. I would talk directly about the roles the two sexes have in his family. Then, listen to him carefully.


Week of November 18, 2000


Dear Mrs. Web,

I once dated a woman and later found out she really didnít want to go out with me. She was just bored. Now that I am seeing someone new how can I prevent this from happening again.

Nothing is totally preventable. However, I do think that it is important that you discuss honesty with your friend. Tell her you plan to be honest in your relationship with her and you expect honesty from her.

Dear Mrs. Web,

This is my question: I know a wonderful and kind man. I think I could spend the rest of my life with him. The problem is this: He lives on the East Coast and I am on the West Coast.

I have no idea what the guidelines are for long distance relationship. If we decide to marry, who should to whose state? I know I am very willing to move East, though I have all my immediate family and friends where I am. However, I need advice to make sure I am making the right moves and choices.

Your are at the beginning of discovering the heart of this man. You are both going to have to communicate, communicate, and communicate! Have you looked at and printed out my Questions for the Beloved? This list will help you know and understand each other.

If your relationship progresses, you will both need to make the decision of where to live. This decision should be made for the benefit of both of you and your future children. You will both weigh career plans, family hopes, family support systems, etc. and try to project and imagine the kind of lives you want to live. 

If you have high-powered career plans and he would like to stay home, paint pictures, and raise the children, it will be one choice. If you want to be the baby-tender and he wants to hunt down the paycheck, of course, you will make different plans. If you find it imperative to live and raise your children near your extended family, other issues arise.

Developing a relationship is designing a future, together. Successful marriage is negotiation, communication, and passion.

Dear Mrs. Web,

I have been corresponding with a man via the Internet for the last 2 months. Daily exchanges, slowly getting to know each other. We are both in the process of being divorced. After 6 months alone, I find myself wondering if this could develop into something real and lasting. I am not able to judge. What is your advice?

There is not enough information here for any sort of judgment whether your Internet relationship could develop into something real and lasting. It sounds like two lonely souls exchanging electrons in the night, not a real grown up relationship.

What concerns me most regarding your letter is that I am not reading about any sort of responsibility or insight into your previous marriage. Instead, I read that you were separated four months and then found someone else to wrap up in. Someone who isnít even real flesh and blood. It seems surreal to me.

A real and lasting relationship has everything to do with the commitments and decisions of the participantsÖand the choices they make in partners. Choices like learning what they can and cannot live with as far as personal habits philosophies, values, and beliefs. These insights are hard work and take time and commitment to really know yourself first as well as the potential beloved.

My site has a section called To: Questions and Issues to Explore with Your Beloved located at the end of my Dating Column. It is for people to use individually to get to know the self better, and with a potential love interest, to help decide whether there are enough similarities to move a relationship to serious ground.


Dear Mrs Web,

Why is it whenever I hang out with women from work, they act as if I don't exist? I try to flirt effectively, compliment them, and look in their eyes. They treat me poorly or ignore me.


People say I'm good-looking but I seem to strike out with women. Why donít they like me? Am I doing something wrong? Do I have a bad attitude? How can I flirt more effectively?


The statement "I try to flirt effectively, and compliment them and look in their eyes Öbut they treat me poorly" tells me that you are not aware of what messages you are sending out. My guess is that you want to send out verbal and nonverbal messages saying: I like you, I am interested in you, and, do you like me?


I suspect your messages are saying something else, altogether. You may need help deciphering what you really are saying. Do you have a sister or cousin who can help you with this? If not, singles group therapy can work well on our messages to the opposite sex.


Week of November 12, 2000


Dear Mrs. Web,

I am a person who likes predictability. I really donít like changing at all and find most change very stressful. I am 22 years old. My mother has pointed out that my dislike of change seems to affect my life. What should I do?

Some people flop in any direction, relying on the winds of style or popularity to give them direction. Others are so stiff and rigid and endure the breezes easily Ė but snap quickly in heavy storms. Strive to be like a reed, upright and flexible, ready for whatever the weather brings. 

The best way to achieve flexibility is to truly understand that the only constant in life is change. It is inevitable. Translated: Change Happens.

Dear Mrs. Web:

I am single and self sufficient with a good job, nice clothes a good car and have a healthy stock portfolio. I do not make a lot of money, about $26,000, but I can stretch it well.

Recently my boyfriend of 4 years was surprised at how little I make, he thought I made much more. He makes quite a bit more than I do. How important do you think my salary is to him? Do you think it might prevent us from having a future together?

I donít know how important your salary is to him. It depends upon what his hopes and plans are for the futureÖfor example, is he hoping for an at-home wife and children? Is he looking for someone to equally share the burden? Is he looking for a babe with a trust fund to smooth the roads of his life? This is important information to know. After 4 years together, this is information you should have.

By the way, in my opinion, your excellent financial management skills and thrifty ways would be a real plus to most potential mates.

Dear Mrs Web,

I am thinking of being transferred to another state for a better position at work. My ex-wife and son, age 8, live here. I want fly back once a month for a four-day weekend and have him on holidays. I currently see him once a week. He is upset that I am moving. I think his mother is putting him up to this and getting him wound up. What should I do?

I donít think your wife has to "put him up to this". It is normal for a child to become very upset when losing a parentís care. He has already lost your 24/7 care. Now your are dropping your visits down to once every thirty days. He knows you are slipping out of his life. He is feeling abandoned.

I think your son is telling you he needs you and wants you in his life. Face it and give him what he needs, an available, and caring Daddy.

Dear Mrs. Web,

I'm a 28-year-old professional man. I was married and divorced when I was very young. Since then, I have only dated two women steadily. They both had the total package of qualities I want in a woman. I messed up both relationships because of my own issues. I am in better shape now.

I am interested in a young woman I recently met. She has the total package I want: it is hard to define: but it is the way she looks, talks, walks, laughs, her eyes, lips, hips, and more. She seems to flirt with me, but I canít really tell if she is interested. How should I approach her, what should I do?

Two issues here: the first one is how do you approach a flirty young woman (or any woman for that matter). You approach her kindly, openly and honestly. The best way to get to know someone is not to do the high-pressure date. Instead, work with them on a project, rock-climbing classes, skiing lessons, feeding the homeless, building a canoe, cooking classes, folk dancingÖthe list is endless. 

I think suitors should build foundation stones in the relationship, one small block at a time, learning and evaluating their love interest. One can be tongue-tied or enchanted by a womanís physical attributes, but still one does not give oneís heart to an emotional or philosophical stranger.

This leads me to the second issue - the package. I was surprised at how one- dimensional your "package specifications" are. You essentially stated only physical qualifications.

Now, I realize men find the physical package a great attraction, but at your age, with one failed marriage under your belt, I would want to see more depth in your qualifications.

I have a web page designed to help couples explore themselves: Questions and Issues to Explore with Your Beloved  It is a good tool for single people to use to discover what issues things are important to them.  Use it to add to your package qualifications. This way you can get what you want in life instead of chasing kite-tails.




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