Casual Dating

Hi Regina!

I am hoping you can help me! I am a single (fluffy) mom. I am totally obsessed with my life, I love it and every aspect of the chaos we live in, but I am not opposed to some very casual dating.
Here are my three big problems:
I don’t feel comfortable going to the bar as I don’t really drink.
I can’t stand the idea of meeting someone in church, seeing as I don’t go regularly, I don’t want to “lead on” a Godly man.
Lastly online dating apps such as Tinder give me the WORST anxiety what is this guy going to do to me or what if there isn’t enough chemistry to make it to the casual dating part?? Any suggestions?!



Dear Anonymous,

First – I’m not sure if you wrote fluffy as a qualification or disqualification, but I need to address that you are a beautiful person. Inside and out. You are attractive, magnetic, kind, and worthy of love and attention.

Second – My suggestion is your hobby. Don’t have one? Get one. Just think about it – say you like rodeos, right? Even if you don’t compete, but you make a point to go. Go without the kids. Get a little concession food, watch the rodeo, strike up conversations. Someone will surface.

More of a book lover? Schedule time once a week to go hang out at the library and read. Inevitably, people will talk to you.

Enjoying your hobby may help with the loneliness, but it is a really good way to strike up conversations with people who you know share at least one of your interests.

I know you said dating apps aren’t up your alley. So try this instead, find a local Facebook group (or two), that has to do with your hobby. I’m in several reading groups and several horse/farming groups. Start talking and interacting there, make connections, and I could see a casual dating relationship sparking there.

Most importantly, love yourself and don’t settle. Love yourself enough to pick someone who loves you well, but be gracious enough to let them be human, and ultimately flawed, too.

With Love,
Regina W.

Family in Transition

Dear Regina,

What should I do? My husband and I were planning a visit to distant family over Thanksgiving but have recently learned that this family is going through a large transition in their lives which is not a pleasant one. Should we postpone the trip and not invade their home and lives while they are going thru this transition?

Rebecca, Colorado


Dear Mom,

I couldn’t decide if I was supposed to reply with or without the familiarity we share. So, if I didn’t know you, or the situation you were referencing, this is what I would say:

The burden of unpleasant transitions is often eased by the community around us loving us through the changes, and sometimes exactly what someone needs is for family (or friends) to show up, connect, and lend an ear/shoulder. Time is an invaluable gift, and your presence matters to them, I’m sure. That being said, holidays are often a stressful time for people, with increased financial expectations, and the general busyness of the season. If the transition affects the family financially, then you may reach out and discuss meal plans and let them know how you can help with the big meal, but also the smaller meals surrounding the trip. Travel makes it hard to cook and bring specific dishes, but knowing that they aren’t expected to feed everyone out of their own pocketbook may be a relief as they face the transition at hand. Offering to split the grocery bill, or letting them know that you don’t need them to provide every meal while you are visiting will be helpful to them. (If the transition is not financial in nature, and they have offered and are willing to feed you, then enjoy and go be a shoulder!) If you don’t share the closeness with this family that it takes to have a transparent financial conversation, it may be best to postpone the trip.

I have to get personal with this answer and say, please come see us. These transitions are just part of life – changes happen, and we learn and grow in the difficult seasons. I want to see your beautiful face, and Dad’s too. I want to spend time with you and watch my kids interact with you. The meal will worry about itself, but let’s not miss the opportunity to spend time together.

Happy Trails!


Kindness Abounds

Dear Regina,
How did you get to be so amazing? And when can we get together for coffee? I love that you are doing this. You are smart, talented, and so sincerely tender.

Luther, America

Dear Laura,

You are sweet and kind, your words mean so much to me. I can’t wait for our coffee date next week!

As for how I got to be so amazing – I don’t know. I want to deflect and avoid even answering, because the truth is, I have a really ugly way of talking to myself and a nasty inside voice that says I can’t/shouldn’t/don’t measure up. He is loud and a little frightening at times. Sometimes, though, I stomp my foot and stare him down, telling him he doesn’t get to decide everything. And for a moment, I feel brave enough to take on something new and exciting, like this.

I’ll see you soon!

With Love,
Regina W.