When Should a First Date Progress to a Second?

web-sally-640x480Dear Ella,

I hate first dates, and I’ve had quite a few lately. What’s with all the shtick men have now? The first guy seemed normal online and on the phone. We went for dinner and everything was going well, until he reached over and picked up a bunch of fries off my plate. The next guy barely took his eyes off his phone as his annoying text message alert kept interrupting our conversation. I couldn’t help feel the texts were about me. The third guy was clearly not over his ex and couldn’t stop discussing what a bitch she was. All deal-breakers in my book.

Isn’t there anyone left out there that’s normal! I’m so frustrated I could scream. How am I ever going to meet Mr. Right?


Hates Dating

Dear Hates Dating,

Dating is all about the risks and the rewards. You have no choice but to put yourself out there in order to progress that first date into a second one. 

The first impression someone makes may not convey who they really are as a potential partner. You’re meeting a superficial being on the first date, someone who might be nervous, trying to put forward a specific persona, or trying too hard to impress you. On the other hand, he may truly be a jerk and not dating for the same reasons you are.

Time to put your Sherlock hat on and follow your instincts. It’s not easy, and you have to be smart. 

Here are some questions to ask yourself to determine if that first date should turn into a second. 

First and foremost, do you feel safe, not only physically, but emotionally? Is he well-mannered, not putting you down or making you feel inadequate? Do you have anything in common? Does he possess any of the qualities from your short list? Are you bored? Are you enjoying yourself, or is the date a chore? Is your conversation easy or strained? Catching him in a lie is also a huge red flag. Trust your instincts. 

Even if he did or said something annoying, if he passes most of the questions I mentioned, give a second date a try. Give yourselves a chance to let your hair down and get to know each other with the first date jitters and awkwardness out of the way. It only takes one to make it all the way to being that Mr. Right.

Dear Ella,

I recently met a sweet fellow at a party. He asked me out on a date, and I happily accepted. We were out for a walk after a lovely dinner, and he mentioned he would prefer to date women who have children. He is recently divorced and has two daughters 12 and 15.

At first I just thought it was an odd thing to say, but he explained that he didn’t feel a woman who has never raised children would understand that he has to put his kids first. I don’t have kids, and therefore don’t meet his criteria, but I like this guy and his values. Do you think I should bother trying to pursue him, and change his mind?


Kidless & Single

Dear Kidless & Single,

I think on the surface, this fellow is admirable. First, his priority is his daughters, which tells me he is a hands-on dad. Second, he is being honest with you from the start, also an commendable trait. 

The question then turns to you. Are you comfortable taking second place in this relationship right from the start? He is telling you that you will never be No. 1. Can you handle that? Is that what you want?

I think what he really needs is time to adjust to his new lifestyle and experience what it’s like to be in the dating world again. He needs to stop being judgmental if he wants to succeed. Being a mother is not the only criteria that makes a woman understanding. There are plenty of divorced mothers who are ready to be No. 1 one in their man’s life, and there are plenty of single childless women, who may even want to get to know his kids and be part of their lives. 

Although this guy may have his priorities straight, his narrow-minded views tell me he’s not ready for the dating scene yet. He has growing and learning to do. Are you sure you want to be the one to teach it to him? 

An Empty Nest Means You’ve Done it Right!


Whether they’re off to university or to their first day of school, your feelings are real and life as you knew it has changed. You may not realize it now, but it’s a good thing. Really! (CJN column Oct 2, 2015)

Dear Ella,

A few weeks ago, my husband and I drove our son to McGill University in Montreal. On our drive home, we discussed how happy we were to have finally reached a stage where both boys are in university.

Now that it has sunk in and my husband is off to work every day, I am finding myself moping around, constantly depressed. The house is too quiet. When I open the front door, there is no one playing guitar, no music blaring, no mess, no negotiations about the car, and no one expecting dinner. I never thought I would feel so empty. 

I’m very happy for both my sons, but this empty nester thing is truly for the birds. How am I going to move on from feeling so lost and not needed?


Sadly Alone at Last

Dear Sadly Alone at Last

Having your last child leave home opens up a whole barrage of emotions. Everything from joy, relief and well-deserved pride for having done a great job as a parent, to sadness, worry and loneliness. You have entered a new stage in your life, and you need to allow yourself time to adjust. This is also a new phase as a parent, as a wife and as an individual.

You’ve raised your boys with the hopes of getting them to this milestone. You’ve given them the tools they need to become productive, self-sufficient adults, and now it’s time to let go and let them put all the life skills you have instilled to work.

You probably put your family’s needs above your own, and it will take time and action to re-adjust that thought process and fill the void with things that continue to make you feel fulfilled. You could volunteer, go back to work, take some courses, join a book club, travel, join a health club, revive or start a hobby, go out on dates with your husband, get a dog, take up golf – the list is endless.

Remember: your boys are not gone for good, and believe me, they still need you and always will. Allow yourself time to make this new adjustment.

Try to plan your week in advance. In the beginning, you might be lunching a lot with friends you never had time for in the past, but eventually you will want to remake yourself and find the new right fit. 

Remember that your sons are always accessible. You can reach out by phone, text, FaceTime, Facebook or even visits. You’ve done a wonderful job as a parent, now it’s your turn, embrace this new transition.

Dear Ella,

I have three children, 9, 6 and 4. My baby started all-day junior kindergarten this week. My full-time job as a mom has abruptly come to an end. 

Usually, when the bus picks up the older boys, my daughter and I begin our full day of activities, but when I waved good-bye to her this morning, my heart sank down to the pit of my stomach. I spent so much time preparing her for this moment, but I never thought about what it would do to me.

I jumped in my car and chased the bus, only to find her getting off at the other end seeming quite content. She wasn’t in tears, but I was! I cried all the way home. I should be happy, not miserable.


Baby in School

Dear Baby in School

Relinquishing the care of your last baby to someone else, a virtual stranger, is certainly traumatic, and there is no reason to trivialize it. However, your job as a full-time mom has not abruptly come to an end, it has simply changed. 

You just went from being needed every waking moment to an empty house for a few hours with time for your own thoughts and the luxury of making your own schedule without a kid hanging off of you. Your feelings are real and natural, and you have to allow yourself the time to work through them – time to grieve your old routine so you can create a new one that’s just as productive.

You’ve done a great job as a mom in the last nine years raising your little miracles to go into the world. Although it’s a difficult change for you, it’s also a good one. Time to add another layer to your already accomplished, full life.

But remember: you only have a few hours until that school bus arrives and your house is full of kids once again, all shouting mommy and needing you like they were never gone.