Dating Advice: How Do You Know If You Really Love Someone?

dating advice

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

“How do you know if you’re really in love?” is the question I answer in my Love Essentially column, published yesterday in Chicago Tribune Media Group publications. This is some dating advice you’ll really want to hear!

How Do You Know if You Really Love Someone? by Jackie Pilossoph

I have been dating a woman for four years now. She has a lot of problems with her adult son, who is autistic. He is college educated, but recently lost a job he had for over 15 years. How do you know if you really love someone, even though she has these problems to handle? I like her very much and even think I love her. She’s been very faithful to me and we have a good relationship. I don’t know if we will ever get married. She has two other problem adult children.

Four years is a long time in a relationship, which leads me to believe you really care for and love this woman. That is wonderful! A connection like yours doesn’t happen very often.

The thing is, every person on earth has problems, and truly loving someone means loving them despite those problems, not to mention faults, bad habits, mistakes, quirks and anything else that might not be easy or fun to deal with.

Love isn’t something you decide to have under the right conditions. True love means loving ALL of someone. In other words, love is a package deal. When you go to the grocery store, do you buy one egg? No. You can’t. You buy a dozen eggs. Your girlfriend’s problem children are the other eggs in the carton. That leaves me with a question for you: Do you want to buy the whole carton of eggs or do you not want any eggs at all?

The choice is yours. You can love her and support her during the tough times she has with her children, and you can even try to help if you choose. Or, you can decide you don’t want to be a part of those problems, break up with her, and never have to deal with her children’s issues, ever again. That’s the choice.

It doesn’t sound like you want to end it. You say she’s faithful and that you have a good relationship. Furthermore, it is clear that the two of you have stood the test of time — four years. All these things are very special and important.

When it comes to relationships, there are two must-haves for it to work long-term: trust and loyalty. Those are the biggies. Ask yourself if they define your relationship. If they do, I’d hang on to her!

Lastly, regarding your comment, “I don’t know if we’ll ever get married,” my response is: Who said anything about marriage? Why do you have to know right now? Unless she is expressing an interest in wedding vows, there is no reason to put it on the table. Just continue enjoying the relationship.

I think couples who are in a long term relationship put way too much pressure on marriage, like there’s a time limit on how long you are allowed to date before you must get engaged. How about just living your life appreciating each other and letting the natural progression of time dictate what happens?

It’s probably very annoying when someone asks, “Are the two of you ever going to get married?” So, the next time that happens, just smile and say with confidence, “We’re not sure, but for now we’re really fine with the way things are, and we’re EGGtremely happy!”

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

One Response to “Dating Advice: How Do You Know If You Really Love Someone?”

  1. Do I or Don't I

    Dear Jackie,

    You stressed two must-have’s for a successful relationship; trust and loyalty. But is that enough? I’m in a 30 year marriage which has been a mixed bag throughout the entire time, although I can say that I have been in love with my wife for most of the time if not all of it. I can also say that we’ve been through some incredibly stressful and difficult times as most people face in life which naturally strains, changes and challenges the relationship . We have clearly grown apart in who we are today. I do believe that we have a good deal of trust and loyalty, although due to the various stressors in our lives there has been lots of negativity, resentment, and unforgettable behavior in our relationship, which makes me question if I love her and to my lesser concern…if she loves me. I accept that it won’t be like it was 30 years ago, but is my love for her still there and just buried beneath tons of negative feelings? At many times, There is so much resentment, anger and maybe even hatred towards one another because of our problems. It’s very possible that one or both of us have fallen out of love with the other which is the way it seems. We both deserve to be happy of course but as we are in our early and mid-50s, there’s not too much time left to get on the road to happiness without making some decisions and acting quickly. So I guess my question is, putting trust and loyalty aside for the moment, how do you know if you are still in love with someone when you really don’t feel it and can we and/or do I want to try and turn around what has been a very difficult, maddening, and almost unbearable existence/relationship for the last 5+ years, or just move on and start a solo journey or fresh start towards my own happiness?

    Confused & Contemplating


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