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Dating Tips Advice Column:
Can Old and Far be Near and Dear?

Dear Dating Tips,
I'm a 49 year old Chicago gal, looking for a nice man to settle down with. I have lived in Chicago 49 years and still haven't found what I'm looking for... think that's a song, isn't it? Anyway, I have been speaking to men from far away states, 500 plus miles; It's been wonderful and I wondered if I could actually have a relationship with one of real life? What do you think? What are the chances of that working out and if the chances are ok, how can I help make it happen? Thanks. ~ Lovin, but Not Local

Dear Lovin, but Not Local,

Long distance relationships are a challenge, but if the person is right for you then it can work.

First, you have to approach the situation realistically and ask yourself this question: If you fall in love with this man, will you be willing to leave Chicago and move 500 miles away? It sounds like you have deep roots in Chicago. If you're not willing to consider moving in the future and the man isn't willing to consider it, then the ability to move your long-distance relationship to the next level will hit a stale-mate.

Outside of phone calls and visits, here are some things you can do to keep things alive:

1) Little surprises. Out of the blue send him/her via snail-mail a "thinking about you" card.

2) Love notes. If you visit the person at his/her place, hide little "love notes" around their place for them to find. If you mail them, include a secret coded love note.

3) Care packages. On special occasions put time and thought into a nice care package for the other person. The more personalized it is, the more impact it will have.

4) Flowers for special occasions. For guys, when a special occasion arises, make sure a bouquet of flowers are delivered to her at home or work. Alternatively you can have neat balloons or teddy bears delivered. Make her know that she is special and that you are always thinking about her.

5) Learn to be expressive. Because your relationship is long distance, you need to become good at expressing your feelings through the phone, email, and letters.

6) Stay balanced mentally. Keep yourself always mentally healthy and balanced by eating good and exercising. You can even set a goal to look much more improved before your next meeting as a "surprise" to your significant other. But more importantly, staying balanced mentally helps you to cope with the distance issue.

6) Keep things fresh. Long distance relationships can start to go stale after awhile when you forget about the thoughtful things you did at the beginning of the relationship. Be consistent in expressing your love for that person.

Also, look for good phone calling plans that don't break your budget. For example, Costco sells 670 minute long distance calling cards for only $20 (can you tell I've done this before?).

Yes, long distance relationships can work and have for tens of thousands of people. It takes a lot of hard work, but if this person is the right one then the payoff is big. ~ The Dating Tipster

If you have a question for The Dating Tipster, simply email your question to Most questions are answered within 48 hours and your privacy details (i.e. email address) are always kept confidential and never used for any other purpose).

How has your experience with online dating or relationships been? Take a moment to share your experience! Our readers appreciate being able to read, and learn from, the experiences of people like you.


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