Are you emotionally ready to begin dating again?

A 7-year-divorced, midlife friend is starting to date again after a few-year respite. A few years ago, she fell in love with a man who seemed equally infatuated. They dated for six months, having sleepovers several times a week. It seemed this relationship was going to be long-term, so she took the plunge and introduced him to her teenage daughter, something reserved for very few of the men she dated.

On a business trip, immediately upon landing she turned on her phone to tell her sweetie that she’d arrived safely and there was his text: “I’m married.”

We can only imagine the pain, anger, betrayal, hurt, and confusion she felt. Needless to say, it’s taken her a while to reenter the dating pool. Which she did recently.

She shared, “I met someone online. I liked him but since I’m so rusty, I was nervous on the first date. He gently put his arm around me and I couldn’t believe I said, ‘Don’t touch me! You don’t know me well enough.’”

Now we feel compassion for her, don’t we? We understand how one can be nervous around someone whom they’ve become fond through emails and phone conversations. A kind, loving, caring man would give her some grace because of the pre-meeting connection they’d shared.

But her story doesn’t end here.

“A few seconds before my blurting out at him, I tensed up, clutching my arm to my body. My phone, which was inside my pocket, randomly dialed my daughter’s friend. She heard me tell him not to touch me and thought I was in trouble on this date. She proceeded to call everyone who she thought knew me to tell them something was wrong on my date. So everyone started texting me and warning me to stay put and someone would rescue me. Poor guy, he thought I was completely nuts.”

Oy! She’s now testing every ounce of patience he has. Any deposits she had made to his Bank of Grace are close to being — if not already — overdrawn.

She didn’t share how this date ended, or if it ended right then, or if she ever talked to him again. But I understood — and I think she did too — that she wasn’t really emotionally ready to begin dating again. Her nerves were a bit too raw and her ability to graciously express her boundaries was nonexistent.

What could you do if you find yourself similarly unable to cope? Admit it. If a man does something that unwittingly crosses your boundary (e.g., first date hand on knee, passionate kiss, or other PDA), you can simply say, “I haven’t dated in a while and it will take me a little while to get to know you and feel comfortable with PDAs.” Or, “I’m a bit rusty at dating, so I’d like to take it slow.” Or, “I love PDAs but I have to know a guy a bit longer to feel comfortable.”

My friend is an intelligent, sensitive, thoughtful woman, so I’m guessing that after she pulled away she said something like the above to him. And hopefully he/they could laugh at all the texting drama. It could happen to any of us.

No matter on which side of this scenario you might find yourself, it’s telling to see how each person reacts. If she didn’t apologize for her brusqueness, that says a lot about her. If he didn’t accept it, that tells us a lot about him. If she didn’t laugh at the texting and say something like, “It’s great to have so many friends who care about me,” she’s taking life much too seriously. (And she needed to respond to all the texts to assure her friends she was fine.) If he didn’t laugh along with her, he’s not putting himself in her place.

Missteps happen in dating. And how you both react tells you a lot about your emotional readiness to handle the inevitable ups and downs that dating usually entails.


Date or WaitIf you find yourself wondering if you are ready to date again then Date or Wait: Are You Ready for Mr. Great? is the perfect book for you.


4 responses to “Are you emotionally ready to begin dating again?”

  1. Ruby W Avatar
    Ruby W

    I know what you mean .. I have been wondering why all the men I’m attracting are married or otherwise unavailable. Until a friend asked me “are you sure YOU’RE not the one who’s unavailable?” And, despite part of me that thinks it wants to be in something long term, I know I’m not ready yet ..

  2. Patty Evans Avatar

    Great post – I think many of us have our own horror stories when we begin dating again. But it’s great if you can find the humor in it and go on.

  3. Terry Avatar

    Gosh, there’s a special place in hell for a man who sleeps with a woman several times a week and then texts, “I’m married.” What a loser.

    After a divorce and that disaster, I don’t blame your friend for freaking out when she started dating again. One day soon, I hope she’ll be able to attract and accept the love she deserves.

  4. Jack Avatar

    Interesting post. I was on about a 3 year post divorce run of completely misreading the signals of the women I was interested in. I realized I was really misreading myself. No dating for a while and maybe a long while. Taking a break has let me assess what I value and am looking for in a mate without causing any pain or confusion in another person.