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Dating Columns Archives



July 26- August 1, 2002


Unaffectionate Man,

How to Hold Hands,


Suicidal Ex-Boyfriend



Dear Mrs. Web,

My boyfriend and I (in our mid-fifties) have dated on and off for 5 years. We have a good relationship, and, enjoy a lot of the same things. I am attractive, shapely, and fit. I enjoy kissing and cuddling; I love that feeling of closeness.


My boyfriend very rarely kisses or cuddles me, except hello and goodbye. When I bring the topic up, he says that he does what he feels like doing, and, when I  mention the lack it makes him feel that he has to do it on demand. He said that if I want him to be more demonstrative, then I have to work towards that goal.  He says that I should consider what it would take for me to entice him into kissing me.


I think that kissing and cuddling are natural for two people in love. I feel that my boyfriend is not sufficiently attracted to me. Why is he like this and what should I do?


I think you have a man who equates kissing and cuddling with sex. There are men like that. They are not demonstrative in any way. It sounds like he is not taking any responsibility to change to meet one of your needs, but is instead placing all the responsibility on you. Is that what you want??


You need to decide what you can live with if he cannot or will not change.



Dear Mrs. Web,


How do you hold hands? Does the girls thumb go under the males thumb?

What a refreshing letter!


Your thumbs go where they are most comfortable for both of you.


Thank you, Dear Mr. Web, for letting me borrow your thumbs while I experimented.




Dear Mrs. Web,

I am 16 and just broke up with a guy who is 20. We dated for 3 months. I was his first girlfriend. He became very attached and wanted to settle down and have kids. He was trying to get a place fixed up to live in on his own. He wanted me to come live with him. My parents would not have liked that and I don't want to settle down yet.


He does not understand why we broke up and thinks there is another guy or that I am not interested in guys. I saw him at the store the other day when I was with friends and he just turned and left. I just want to be his friend.


What if he messes his life up or does something stupid because of me? I asked him one day if he would ever hurt himself after we broke up and he said probably if nothing was going right in his life. Sometimes I wish that I had never gone out with him. But this is just another thing in life to learn from, right?


You are not responsible for this young manís future. Only he has control over his reaction to your breakup. You need to have have your parents alert his family and the authorities if he threatens to hurt himself or you.


If you are breaking up with him you cannot remain friends, you need to release him.


This problem is the result of indiscriminate dating. Dear Mrs Web believes that one should not date until one is ready for marriage.


July 18-25, 2002

Decisive Woman, Fantasy Man, Takeover, Early Marriage, and Internet Love


Dear Mrs. Web,

I am a 24 year old guy. I love this girl very much and want to marry her. I am quiet guy she is really funny and talkative as well as caring and loving. She is also very decisive and can make up her mind quickly. I spend a lot of time mulling over my choices and sometimes her snap decisions scare me.


My brother and she had an accidental sexual connection once and since then, they both have disliked each other. If I marry her I am afraid that I would be ending my relationship with my brother. The rest of my family doesnít like her much either. They think she is a big flirt. I would appreciate your guidance.

Ahem!  There is no such thing as an accidental sexual connection.

I think you will have to think twice about marrying this girl. Opposites do attract, but people with similar tastes, values and worldviews usually work out better.


If this girl is going to alienate you from your family, I am not sure that marrying her is a good idea. If family is important to you, you will always be shoveling sand against the tide. Visit my Issues to Explore with Your Beloved and see if you have the kind of compatibility that can row a boat in the same direction.



Dear Mrs. Web,


Please help me with my problem. I recently broke up with my girlfriend of 4 years. The breakup was good thing.


However, I really want to sleep with her mother. I know her mother and stepfather rarely have sex and that her mother is sexually frustrated. I also know that she would often ask my ex-girlfriend details about our sex life. I don't want a relationship her, I just really want to sleep with her and fulfill this fantasy. The problem is, I have no idea what I should do. Please help.

You should walk away from this fantasy as fast as you can. You are treading into areas of pseudo-incest and grave error. You will be sadly used by these women.  They are, as mother and daughter, are already inappropriately in each otherís sex life. You will also cause a great disruption between them, and if they both turn on you, watch out. You will regret it if you proceed.


Have you thought of finding a nice woman, getting married and settling down? Home of your own? Picket fence? Babies? Stay in the light, guy; donít flirt with the edgy. Most people fall off the edge when they dance there. Dear Mrs Web knows.



Dear Mrs. Web,


I have been dating this girl for two years. She moved into my house 8 months ago. I am 27, and she is 21. Everything has been great.


However, she has a very close relationship with her mom. They talk on the telephone an average of five times a day, and her mom sleeps over at our house at least four times a month, sometimes for an entire weekend. Mom lives about an hour away, and expects to be able to come in town, and stay without asking permission, and with little warning. She is usually drags along her husband, and their dog and cat. If I am not happy about their arrival, my girlfriend starts an argument.


We live in a two-bedroom townhouse, and we don't have a ton of room. Whenever I try to discuss this with her, I end up looking like the bad guy. I don't know what my next step should be. Can you give me some advice?

This is your future; you need to decide whether this is what you want for a life.


It sounds like your roommate is involved in her family and that you are an add-on feature.


Dear Mrs. Web,

I am 18 years old and a freshman in college. I am dating a man I met last year. We have an amazing connection and indescribable chemistry. He lights up my day with merely a smile. About a month ago, he went away to work for the summer. I'm proud of him and fully supported his decision. We promised to stay in touch and he plans to return next month. I can't wait.


At 18 how long can a relationship last between two ambitious young people? We both want to further our education and we both want good careers. However, we have years of education that will take us to separate states. I know that young relationships don't usually last. What are our chances? Could it last? Is it possible to stay together through college? Would it be wrong to follow him? Please help!

Relationships without the commitment of marriage rarely last a long time even when children are involved. If you both want to build a life together and are willing to work your plans out (plans that also makes room for the unexpected blessings of children), then get married. Up until about twenty years ago there was always married housing on college campuses.

If you both do not have the forever commitment of marriage, there would be no real reason to change your life plans for each other. So, donít bother. Never change your life for someone without the commitment of marriage.



Dear Mrs. Web,


Do you think it's stupid to be in love with a person over the Internet? The local guys are jerks.


I've met this guy online and we've been talking for quite some time. I've never ever met anyone I could trust as much. I would like to continue our relationship and make it grow. But I am afraid that people are going to think I am weird.


He says he loves me a lot. He helps me with my problems and makes me feel special. I really do think he loves me. He hasn't lied to me, I just know he hasn't and he really wants to meet me and I love him so very much. What should I do?



I donít think that the word I would use would be "stupid." "Deluded" perhaps, or "lonely," but not necessarily "stupid."


You do not know this man, you just know who he says he is. He could be someone totally different. There is no real connection here yet. What you love is not real. Your judgment is blinded, so you need to make sure that someone who loves you, parents, friends, or church friends are involved in your meeting and getting to know this man in person.


The bad thing that has happened in this relationship is that your heart is opened to someone who is not real. Therefore, you could be badly hurt, emotionally or even physically.


Usually a man and woman meet within context of friends and family. You both have bypassed this. So, if you are going to get together, have him come stay with a friend or family member for a week or two and get to know him better. Then go stay with his family or friendís for a week or two. Perhaps it would be safer if you brought a friend or brother with you for your visit. Meet his family and friends and get a good picture of this man.




July 1- 12, 2002

Dear Mrs Web,

Every time a young man I am attracted to says or does something nice to me, I fall head over heels in love with them, I have no idea why, and this happens all the time.

I even fall in love with men I meet for the first timeÖand I think that they love me. When I see them again they either completely ignore me or flirt with another girl.

I set my self up to be hurt. I know I shouldn't get my hopes up about a guy but I always do. What do you think I should do?

You have no boundaries. You do not have a grown up sense of yourself and emotional discipline. You are enjoying the emotional ride of your fantasy life about these men you really donít know. You are putting your hopes and dreams into the shells of the young men that you have met. You have not bothered to acquaint yourself with them. In other words, you are using them. You need to protect yourself and develop some self-discipline.

Sometimes young women think that everything that is happening is about them. It is a psychological stage. Therefore, young woman will misinterpret a young manís actions because she thinks that his behaviors pertain to her inner state. Emotional maturity is the cure here.

Dear Mrs. Web,

I have liked this guy for one year. We dated for 2 months and we broke up because he was seeing five other girls.  Except that all I want is to be with him. I know that I should have more self-respect but I think I love him. He is now acting like he wants to be with me. He says that he has to wait until he is sure. What should I do??

Dear Mrs. Web wants to know how many time you will hit yourself with a hammer before you realize you should stop. You know this young manís poor character. Why go there again?

You need to look at your criteria for involvement with young men. It appears at this time to involve only two things: ďbreathingĒ, and ďgives me a second glance.Ē In your shoes, I would require much more of my potential beloved.


Dear Mrs. Web,

I met a guy at work who I like. We started to get to know each other after I initiated my interest in him. The feeling soon turned mutual. We flirted constantly, and he complimented me often.

A week later I found out that he has a girlfriend. I confronted him about it. He said that he felt bad and that his feelings took over. We are still close, and he still flirts with me. What should I do? Should I pursue a relationship with him?

Why would you pursue a relationship with a man who is still entangled in another relationship? You should make it clear that you are interested, but if he wants to pursue you, he had better do the honorable thing and end his interests elsewhere. Otherwise, he is a bounder and a cad.

Spend no time or energy on cads.

Dear Mrs. Web,

To make a long story short, I have been having romantic feelings for my 3rd cousin. The feeling is mutual and we both know it is wrong. Nothing has happened, but I am scared our emotions might get the best of us. What can we do? I don't want to feel this way. Any suggestions would be greatly appreciated.

I am not sure that your love is forbidden. I would check with a local lawyer but I think the incest laws do not extend to 3rd cousins. Check this out first before buying the rings. Another place that might know is the marriage licensing office.

Dear Mrs. Web:

Several years ago I met a man on the Internet (I know, I know... not a good thing, but this is different). He was quite a bit younger than me (a May/December romance) but his maturity level is equal to mine. We began corresponding as friends. Then we fell in love, despite having never met. I was married; he was not.

We felt strongly that we were soul mates. My marriage was in trouble. I broke off my relationship with my Internet friend at that point and tried everything to patch my marriage together. Subsequently, I divorced my husband.

I restarted my Internet relationship, but after a few months I met a local man and got pregnant. My Internet friend found out about the baby, and I have not heard from him since. He has not answered my emails, and when I leave messages at his parentís house, I suspect they are not passed on to him. I am sure his parents do not approve of the age difference (also my ex contacted the parents and said terrible things about me)

I have tried looking for him and I don't know if he has tried looking for me. My last name has changed. Do you recommend I continue to try finding this man or should I just leave well enough alone? I have felt so empty for so long and feel I will not be a whole until we are together.

You are spending your life slipped down a fantasy-hole, dreaming of a man you never really met and donít really know. A fantasy has got in the middle of your life and real time relationships

I think that you have a lot on your plate at home. Perhaps it is time to learn how to get off the fantasy merry-go-round and stop carrying this long-term torch. It is time to be in the here and now with the people who are really in your life. 

Dear Mrs. Web,

I am a 16-year-old girl. I have been going out with my 15-year-old boyfriend for a month now. I had sex with him for the first time a couple of days ago.

It was my first time, but he doesn't know this. He seems to think that I have a lot of experience. I want to tell him that I lost my virginity to him. Is there any reason why I should or shouldn't tell him? I really like him, but I have trust issues with guys due past experiences. If he finds out that I haven't told him the truth, he'll think I don't trust him.

I cannot imagine why this would be such a big deal. You had first time sex with a boy you have been dating for a month -  30 days. You obviously do not have a value system that puts much value in virginity. In fact, you took pains to hide your virginity.

If you have such big trust issues with guys, why would you trust your body to a boy who is not committed to you?

The reason you want to tell him is that a young woman will emotionally bond to the man she gives herself to sexually. Women are built that way. Men are not, and though your virginity has some meaning to you, it will not have much meaning to him. That is one of the reasons why intelligent and prudent women keep their virginity intact until after the wedding.


Dear Mrs. Web:

My boyfriend and I have been together for 5 years. I live with my mother. My boyfriend has his own house. We spend almost every night together. We get along great. He says he plans to marry me.

I feel that since we spend almost every night together, that a courtesy telephone call would be needed to each other when we have other plans. If he could just say that he has a meeting or whatever and we won't be spending the night together, it would let me plan my own activities for the evening instead of me receiving a telephone call at 9:30 p.m.

He has a cell telephone. I have voice mail at work and an answering machine at home.  We have the technology!

He says I shouldn't put such emphasis on receiving the telephone call. I think it is the respectful thing to do.

You are not wrong. It is respectful. However, it is not necessary.

You have no contract or commitment that would require you to share plans with each other.


Dear Mrs. Web,

Iíve tried to flirt with boys but I'm very shy and I can't make eye contact with them unless they talk to me first. Can you tell me how to begin a conversation with boys?

If you are unable to begin or sustain a conversation with a boy, you are too young to be talking to boys. Young women who are able to talk to boys are mature enough to ask him questions and be interested in what he is saying.

Check out my Dating and Relationship books on my website.




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