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4 Things never to say when your single girlfriend is discouraged with dating



Jacqueline Halbig von Schleppenbach - published on 05/30/19

... and what to say instead!

Being single can be a rollercoaster of emotions. Some days you’re fine with your current life and some days you feel like maybe you shouldn’t have broken up with that cute guy who seemed great on paper even though he made you feel worthless. You know, the guy you thought might be your last hope. But you’ll have to trust me on this — he wasn’t.

If you had asked me at 25 or 30 what was so hard about my journey of singlehood, I would have said “nearly everything.” Loneliness, every financial stress, going home at Christmas alone, going to Mass alone on Christmas Eve, practicing chastity for years on end when those I dated thought of it as an exciting challenge. It was tiresome, discouraging, and most of the time the journey seemed to be getting the best of me. Those are some of my own struggles – not necessarily shared by all women.

But there are things we say to unmarried friends, especially women, that are tiresome and painful to hear. Most people mean well and simply don’t know what to say, but even if there’s a grain of truth in what they say, a woman who is disheartened in her search for a partner in life does not have the bandwidth to hear it. Here are some of the things not to say to a single woman who hopes to be married:

“Timing is everything.”

This has more truth than I want to admit, but as a piece of encouragement it often falls flat — or at least it did for me. What does “timing is everything” really mean? To a woman who’s been dating  25-plus years, all she can think is “Who decides when the time is right? How can I expedite that time so it happens sooner?” Even if she realizes that timing is out of her control, this can leave her feeling hopeless and even forgotten by God.

“Expect it when you least expect it!”

Phrases like “expect it when you least expect it’ or “when you’re not looking, it will happen” are also problematic. It seems impossible not to be looking when your heart feels certain your calling is to be married. In my experience, I tried really hard to not expect it. I tried very hard to not look. But finding love was the only thing that seemed impossible to achieve and that frustration was compounded by disappointment when a relationship didn’t feel right or go right.   

“Gosh, I don’t know what I would do if I were you. There just aren’t any good men left.”

First of all, that is simply not true. We know that there’s a God in heaven and He’s at work and continuing to shape, mold, and convert hearts — including men’s hearts. He’s always creating and working with us and our situation. Second, your friend may already have that exact fear, so saying this is not helpful. Hope is a virtue, and we must help fan its flames.

Don’t be too picky!

Among the most frustrating things said to me were “Don’t be too picky!” and “You’ve just got to get out there!” Excuse me? Picky? There’s a 50% divorce rate and we’re talking about the rest of my earthly life and you don’t think I should be too picky?” And by the way, I’m out there and I’m doing everything I know to do and it’s just not working.

While loneliness is painful, there are worse things than being single — like being married to the wrong guy, or a guy with addictions, or who lacks virtue, or who is unable to love his wife and family. That’s all much worse. I have four close, faith-filled girlfriends who were married and are now divorced. Two married very worldly and successful men. The other two married pastors. Yet, all these husbands were unfaithful. Some were addicted to pornography, some were into drugs and prostitution, and as a result they were unable to love and commit themselves to marriage.

I asked these friends if there were signs. Two of them told me they knew better before they married but just didn’t want to break up and start the whole dating process over. They were very tired of dating. Being tired of dating or afraid of being alone is understandable, but being married to the wrong person can easily turn life into a living hell – and is a very bad reason to get married to the wrong person. 

So what should you say to someone who’s painfully single and dating?

For starters, think positive words of encouragement, truth, and empathy.

Encouraging words

The basis for all of the encouragement that we share comes from this truth: He who created the world and everything in it loves you completely and has not forgotten you. God is always creating and working with us and our situations. So we can find encouragement in that, and we can speak encouraging words of hope and confidence to those who are dating.

One of my good friends, during one of the most discouraging breakups I had, told me this:

“Jacqueline, I have no doubt that you are going to get married.”

I couldn’t believe her confidence, but I felt very encouraged by it and it really picked me up. She mentioned the Blessed Mother’s role at the wedding feast in Cana, saying, “Remember how they ran out wine and Our Lady said (paraphrasing) ‘No big deal, we got this!’ Keep entrusting this into her interceding and prayerful hands. You are in a perfect place to choose wisely! You know exactly what you are looking for.”

This gave me hope and confidence.


We all need and appreciate empathy and validation. Something that was said to me many years ago by a married man who was quite a bit older than me stuck with me. He said, “I am sure this must be frustrating for you! I know you have been at this for a long time, but when you meet the right one you are going to appreciate the gift of your relationship more than most.”

And he was right. Because I had to wait so long to meet and marry my husband, I had a profound appreciation of and gratitude for my marriage once it happened.

“You are beautiful”

Every woman I know appreciates being told what is beautiful about her! And sometimes it just needs to be said. It can be especially helpful to single women who experience failed relationships and don’t have a companion in their life to affirm their beauty and worth. So feel free to be generous with your compliments.

Read more:
The secret to finding love when you’re (painfully) single


Read more:
How to balance vulnerability and honesty when you’re dating

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