Real life is nothing like the movie Pretty Woman

Hey there, time traveller!
This article was published 25/11/2017 (3230 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I am a male in my 40s, married for half my life and from a conservative background. I have a half-grown daughter. For the last eight years, I’ve not been intimate with my wife. Over the years, our love has dwindled and the only common thing we share is our love for our daughter.

I have seen several escorts over the last few years. I’ve been seeing a woman more than 10 years younger than me for several years. We have been to a few cities and spent a few days together. I pay her for her time and expenses when she travels with me. I feel a strong attraction toward her, and she says she likes me too. There is a strong sense of passion, laughs and overall we have a good time.

I’m very confused, as I feel a strong desire to just be with her, but I don’t know how the relationship would ever develop if money wasn’t involved. I feel depressed and lonely. Her company cheers me up.

Please help and advise, what should I do to regain myself? — Confused, Manitoba.

Dear Confused: It seems your young-ish escort likes you and the arrangement now just the way it is. How do you think she’s going to feel if you ask her to be your wife or mistress? Is she in love with you or just a sexy friend you pay for? You don’t mention her emotions other than you say she likes you. Does she ever hint at anything deeper?

With other customers gone, it would mean a drastic cut in pay just receiving what you give her as an allowance, and she would have to get different work that pays dramatically less.

She may be industrious and want to work at a regular job with eight-hour shifts, but a lot of people in the escort game are not industrious. The higher-status ladies are getting up to $1,000 per “date” depending on time and what they offer.

Perhaps she wants a family one day. Given the difference in age, she may also have to give up any dreams of finding a guy her age and having that family if she settles with you.

It doesn’t look hopeful for you to be with her permanently, but you could ask her.

You really need a long-range plan. You could make a last-ditch effort to try and rekindle this cold marriage through counselling. If that’s not going to happen, you need to free yourself from this loveless marriage and be generous in your support of the ex-wife and child, then you should search for a woman who’s not in the escort business, is around your age and is understanding about children, or even has some of her own that you like.

Thinking of your child’s welfare, you must decide at which point you want to depart the family. You are already feeling depressed. Staying forever is going to be too hard on you.

 

Dear Miss Lonelyhearts: I’m a hockey freak and so is my ex-girlfriend. My new girlfriend is gorgeous and sexy, but thinks sports are boring. I bought tickets for us to go to some Jets games and she spent the whole time off walking around, buying food and finding people she knew to talk to.

I decided to start taking friends instead. The next game, I asked a buddy and that went great.

The game after that, my ex-girlfriend, who I see at work, came with me at the last minute because I didn’t want to waste the ticket. She asked how my new girlfriend would feel about it and I jokingly said she would be grateful.

A few days later, my girlfriend said someone she knew saw me there with my ex. She’s still seeing me, but she’s as cold as hockey ice.

I told her all we did was watch the game.  I can’t seem to get through to her very often this week, and when I do she’s always busy and has to go quickly. Do you think it’s over with her?  — Hockey Freak, Tuxedo

Dear Hockey Freak: You publicly disrespected your new girlfriend by being out at the game with your ex. Why’s the new lady hanging on at all? Maybe she doesn’t want your ex-girlfriend to think she can get you back just like that, but this new lady has lost trust and sexual feeling for you.

Let her go! It would be a good time to find a sporty woman who is a hockey fan to a certain degree, and at least enjoys the game with you.

Also, find a buddy to kick in some money for a few of the games and go with him a part of the time. Unless you like cuddling up to an ice block, this romance is over.

Dude, what made you think you could go to a big public event in Winnipeg and not be seen by someone who knows your present girlfriend?

You’re not clever enough to do something behind somebody’s back in this well-connected town. You would be best to play it straight from now on.

 

Dear Miss Lonelyhearts: Three men are chasing me: two are younger and one is older.

I just got out of a nine-year marriage that was five boring years too long! My sensual energy is at a very high peak in my mid-30s and I have been entertaining all three of them, and refusing to belong to anyone.

They are all aware I’m dating freely now and say they’re OK with it.

The older one is in his late 40s and very well-known and distinguished. The guy who’s closest to my age is lots of fun, both in and out of bed. He’s close, but no cigar — OK, a small cigar. 

The third one is an old boyfriend who’s come back for another round, so it’s very comfortable and I feel great with him in bed, but he dumped me years ago and really hurt me. If I wasn’t good enough for him then, why would I be good enough for him now?

What do you think? —Three Isn’t the Charm? St. Vital

Dear Three Isn’t the Charm: Keep on looking! These three are OK, but they’re not real contenders for your heart, soul and body. They have not made the cut, and you already know that.

You’re just warming up with them, getting different kinds of support, sustenance and sexual satisfaction. These guys in the frog chorus are amusing, but are not going to turn into Prince Charming, so keep on with your search and stop stressing over it.

The right man will bowl you over, and you’ll know he’s the one.

 

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6