Sometimes life is gracious enough to give us second chances. I believe we should live in those moments in order to take full advantage of the opportunity. And just like life, sometimes a wife will be gracious enough to give her husband a second chance. In that moment he should be thankful and definitely take full advantage of another chance to right his wrong. Before your mind drifts to all the despicable things a husband would need a second chance to right let me tell you about Weeknight Date Night.

This week’s edition of Weeknight Date Night was selected by me, and it was a remix rematch of our July “Goodwill Hunting” date. Last July Anthony and I had a date at Goodwill. We had 30 minutes to select two outfits for each other. We then found a random stranger and asked her to judge our outfits. She picked both of the outfits I selected for Anthony, therefore I won the date. Anthony and my mom both cried foul, because I shop at Goodwill weekly. They felt like the judge was someone I planted in the store. Conspiracy Theory!

Last August I was introduced to a fellow Goodwill shopper named Betsy. We’re actually from the same small town, but never had the pleasure of meeting. She has a blog called Goldwill Digger. The blog focuses on her amazing Goodwill fashion finds. She also has a ton of fashion tips as well as advice on places to shop other than Goodwill that won’t break the bank.

Betsy and I hit it off instantly and we’ve become fast friends. So when I thought about giving ole Hutch a second chance I thought it would be a good idea if he had some professional assistance. I asked Betsy if she’d partner with Anthony and I would be teammates with her boyfriend Justin. She loved the idea and that’s how Goodwill Hunting II came to life!

The four of us met at one of our favorite Goodwill store and the rules were set. Both teams had 30 minutes to find outfits for the other team. The theme was “a night out on the town”. We said we’d meet back up at the dressing rooms at 6:35pm to try on the clothes.

Both teams quickly broke apart and came up with a strategy. Justin and I decided to stick together. We started on Anthony’s outfit first. We found four pair of slacks that were close to Anthony’s style, but we made one costly error! We looked at the Goodwill tag on the clothing but NOT the tag on the inside of the pants. Major Key Alert…when thrifting make sure to ALWAYS check the tag on the inside of the clothing! We proceeded to find a nice button down and blazer to accompany the slacks.

Justin and I then put our focus on finding Betsy an outfit. The tough part for our team was having Justin pick out pieces that were appropriate for a night out on the town and not a night in the house if you catch my drift. We found the cutest brown leather skirt, but once again we didn’t look at the tag inside! I take this personally because I’m a professional thrifter and looking at tags is thrifting 101. In the process of finding a blouse for the skirt there were a few times when Justin got off task and I had to bring him back. At one point he picked up an Elsa shirt. I looked at him and said “Justin, seriously dude let it go” pun intended! While it was easy for him to part with the Elsa shirt it wasn’t so easy for Justin to part with the short black skirt and skin baring black blouse he desperately wanted Betsy to wear. He was a great sport and went with the PG outfit, but my boy didn’t put down the black outfit. He was determined to let Betsy see what could have been. I mean you have to respect a man that doesn’t give up!!!

Meanwhile on the other team they decided to go with a different strategy. Betsy and Anthony split up…tragic move! Betsy clearly didn’t know that Anthony has no sense of my size. It was later told to me that he picked up a size 2 skirt. I don’t think I’ve ever worn a size 2. In my best southern voice “Bless his heart!” I think even more tragic than the size 2 he attempted to pick out for me was the floral grandma cardigan he ultimately decided on selecting. Seriously that cardigan looked like I was ready to teach Sunday School and I had a ton of butterscotch and peppermint in my purse. I get it, I dress like a “fly” grandma, but the key word being fly!

Our 30 minutes were up and the four of us met at the dressing rooms to try on our clothes. Justin was up first and his outfit was pretty good except his slacks were a tad too short. Next up was Anthony. Remember that mistake Justin and I made by not looking at the size inside the slacks? Well yeah, it came back to haunt us. Anthony’s pants were a tad (meaning he couldn’t breathe) bit too tight. I was next and my clothes actually fit. Out of the 4 of us my outfit was the only one that fit. I give ALL credit to Betsy!!! Seeing as how I grew up in the Bible Belt I felt I was missing one major accessory from my outfit…a bible. I ran over to the book section and picked up a book for my pictures. Betsy and Anthony felt I was reaching with the bible, but look below at the pictures. You be the judge! I feel that bible was needed since I looked like a Sunday School teacher. Last was fashionista Betsy and I think Justin and I did a good job with her outfit. Well except for the fact we picked out a size 16! Remember how I said I’ve never worn a size 2. Well, I’m pretty confident that Betsy has never been a size 16.

This date was pretty amazing!!! This was actually our first double date for a Weeknight Date Night, and I’d love to have other couples participate in our crazy adventures more often. Betsy and Justin were too much fun, so definitely keep your eyes open for them again. And be sure to swing by Goldwill Digger to stay current with all the fashion trends. I’m pretty sure you’ll see Betsy and Justin be on the blog again!

Until next week loves…