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Personal Advice Column

Dating Archives

 

Dear Mrs. Web,

Normally, I'm comfortable around women. I date fairly regularly. However, a month ago, I noticed a woman in her mid 20's, who started working at a marketplace near my office. I go there almost every day for lunch. 

Because this woman is probably several years younger than I am, I shouldn't be intimidated. However, every time I get ready to approach her and say "Hi," I lose my poise and walk away. 

Is this something that happens to other guys? What would cause such a "slump"?

Dear Mrs. Web is often unnerved by handsome, younger men, particularly her five year old. "Honey! Please don’t drive nails into the aquarium!"

No, I don’t think you are going through adolescence again! But I do think that you are reacting to her youth and appearance much the way an adolescent reacts to an attractive young woman, viscerally and sometimes even physically.

Yours is not the first letter I have received from men who are unnerved by younger women. There is something about your attraction to this woman that overwhelms your normal poise. Evaluate what that is so you will be able to install appropriate emotional distance so your feelings don’t overwhelm you.

 


 

Dear Mrs. Web,

Three years ago, I met a woman in my major at college. We started dating and had a child together. We had some tough times but we stayed together. Then I had some personal problems and we broke up.

We both became involved with other relationships but they failed and we ended up seeing each other again, sporadically. My personal problems have cleared up and I have done well.

Now she tells me she does not want us to get back together, but she does continue to be intimate with me. She says she feels guilty that we are not married.

Her mother does not approve of me yet she invites me over when her mother is not home. Sometimes she says the oddest things. We were discussing something I was planning to do and we had a small disagreement. She suddenly stopped and said, "Well, we are not together so it really doesn’t matter how I feel." 

When I asked her whether it was a bad thing to be together, she said no. So a few days later with a lot of pondering behind me I risked and emailed her and told her I still loved her and would like to maybe get together. She wrote back mentioning the little disagreement we had and felt we would "kill" each other.

She seems to like me and then she says no, not right now. How do I approach her about my desire to be with her without her becoming upset or defensive? Should I wait for this relationship?

I cannot answer this question without knowing one thing, where is the baby? Creating a baby with someone changes the relationship.

 


 

Dear Mrs. Web,

My boyfriend’s mother and I have had a poor relationship due to many reasons. I was patching things up after my pregnancy, not to mention the drinking episode with her underage daughter. I was back in her good graces after the abortion.

A few evenings ago, my boyfriend and I had a silly fight on the porch of his mother’s house. It was dusk and I walked off the porch and down the driveway swearing at him as I walked away. I did not realize that his mother and grandmother were parked at the far end of the driveway. 

They thought I was cussing them out. They are very angry and refuse to even see me. I don’t want to apologize; I didn’t do anything wrong. They are treating me badly again because they choose to believe the worst about me. How can I get back into their good graces?

Goodness gracious! 

It seems as though you have a history with them, of really making a muddle of things.  So it is only normal for them to expect the worst. 

The only thing I have seen work in these situations is abject, humble apologies. With flowers. And good chocolates. A real crawl. If everyone’s heart is able to forgo the lid of anger and coldness, relationships can work again. 

However, in your shoes, I would treat this woman with a bit of distance.

 


 

Dear Mrs. Web,

My girlfriend and I have been going out for three months. She is a lot older than I am. I am actually not allowed to date and my parents just discovered our relationship. They are trying to break us up. 

They blame her because she is older. They are saying that she is making me disobey them. They refuse to let us be friends or even to let me talk to her anymore. I really like her and neither of us want to break up. What do you think I should do?


Aren’t you the underage boy with the 19-year-old girlfriend? I think you are swimming out of your depth. Your parents have given you limits. I think you need to follow their rules. They have your future in mind and I can assure you that if you are fiddling around with your girlfriend, your future is dim. Do you really want to be a father at 17?

I happen to believe that a true mark of maturity is the ability to accept limits, as well as honesty. Purchase and read I Kissed Dating Good Bye. It is on my website bookshelf. .

 


 

Dear Mrs. Web, 

I am a 16-year-old guy and I am dating a 19-year-old girl. I am wondering if there is any legal problem with our age difference. What is the oldest age I could date legally?

Are you planning to make the hearts beat faster at the Betterdays Rest Home, son?

I don’t think any state would have a problem with a 16 year old dating an older woman. The problems occur if the adult has any sort of sexual contact with the minor. 

So you shouldn’t have any problem…oh, you are?  In that case, each state has different rules about sexual contact with a minor. You will need to call your local police, the state attorney general’s office or look through the state penal code.  

Before you do that though, sign up at your high school for a good active sport like soccer, basketball, or track. You sound like you need a good, tiring sports workout six or seven times a week.

 


 

Dear Mrs. Web,

My boyfriend broke up with me about 6 months ago and is involved with someone else. I still have feelings for him and can’t seem to get over it.

Every guy that I have dated has always broken up with me first. I don't know what I am doing wrong. Recently, I can’t seem to make it to a second date. What am I doing wrong?

Let’s begin with the boyfriend. You are having a difficult time shaking the boyfriend from your heart. That is normal. When we let someone into our heart and soul the way a boyfriend or girlfriend is permitted, we experience pain and loss. We are not television characters, we have many more dimensions, and when we play with our emotions, we get hurt.

That is why I favor courtship over dating. I think it is an emotionally safer path for relationships and the best way to find one’s life-mate.

Next, dating is about shopping. Most people think it is a venue to grow relationships. That is not true because it is such an artificial situation. 

You are not unusual, I hear many women and some men tell me they have a difficulty maintaining a dating relationship.

Get out of the meat market and read I Kissed Dating Goodbye and other books about courtship.

 


 

Dear Mrs. Web,

What is the socially acceptable waiting period to become engaged after divorce?

I don’t think there is a magic number, but one would hope that one waits long enough for children, if there are any, to become acclimated to divorce before bringing in the new model. Divorce is difficult for children; remarriage is difficult for children. Give them some breathing room.

When children are not at issue, I would think some down time between spouses might be edifying. It also gives the extended family time to adjust. In your shoes, I would wait between 6 months and a year. Particularly if there is a trophy in the wings.

 


 

Dear Mrs. Web,

My best friend has been dating this guy for about three years. At the very beginning of their relationship, he and I spent an evening together. We almost ended up in bed but we both realized in time that it wasn't the right thing to do.

I never told my friend about this little moment, and now they are happy and in love. They are planning their wedding for this autumn. I feel that this past event is keeping me from being completely open with her. It was a long time ago and I don't even know if it would really matter to her now, but I can't stop thinking about it. 

I don't want to ruin her relationship or our friendship.  Should I tell her?

No,  of course it would still matter to her.  You and the boyfriend almost made a mistake, but you didn’t. This is both your burden and your responsibility. I don’t know why you want to dump it on her. It would be unkind. Friendship is not about blowing up people’s relationships.

Let me give you one piece of information: friendship is not about being completely open. Friendship includes the flexibility of tact, warmth, and discretion.

I don’t know why you are still carrying this issue around. Quit worshiping and worrying it and let it roll off your shoulders. Moreover, continue to behave yourself around her beloved.  Dance at their wedding with a clear conscience.  You both did the right thing.

 


 

Dear Mrs. Web, 

Is a divorced women known as a "Mrs?"

My grandmother used to call divorced women "grass widows."  I just love the phrase. 

The official formal social title of a married woman is Mrs. John Smith. With a divorcée, if she keeps her former husband’s surname, she becomes Mrs. Mary Smith.

 

 

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