Dear Diary: What Should I Wear on the First Date?

April 09, 2017

Dear Diary: What Should I Wear on the First Date?


It finally happened. The guy I've been eyeing all week asked me for a date this weekend. I drank my celebratory wine, but now I've got to get down to business. I need to find the perfect, eye-catching outfit. Oh, and I can't forget the shoes. I just don't know where we're going, so I have to be prepared for any possibility.

He mentioned maybe going to a club for a drink, so I should have an outfit made for that. I could wear my little black dress with a pair of red heels for that pop of color. When I add in my silver hoops and wear my hair up, I'll be unstoppable. Oh! But what about my strapless purple dress? It's just the right amount of classy and sexy. I'll match it with my black or nude flats, so I'm ready for a night of dancing. It's a tough choice.

Of course, we may not even go to a club. We might end up doing dinner and a movie. Theaters are usually chilly, so I think my green sweater with my skinny jeans would be perfect. I can add in my suede, heeled boots to complete the total look. I should have a plan B, though, just in case the restaurant is warm. Maybe I could keep the jeans, but swap the sweater for a cute top and jacket. I can pair that with my pointy heels and a matching handbag. It's a definite possibility.

I wonder if I can talk to him about taking a day trip. There's so much to do right here in town. Plus, we could spend the whole day together. In that case, I think I'll wear a bubble skirt with a matching top. That always looks good with my knee-high flat boots and a boho bag. Just to be prepared, I could bring a tote bag my white capris, a bright tank, and my white or nude flats. That way, if we stop at the beach, I'm totally on board.

I'm sure no matter what outfit and shoes I pick, I'm going to look adorable. I can't wait to go on a second date with me in no time.