First Date Outfits

Having been single for the majority of the last few years, I have been on more first dates than I can count. Some good, some bad and some just down right awkward. I certainly have quite the playbook of funny first date stories and I’m honestly not quite sure why I’ve been keeping them all to myself. Scroll to the bottom of this post to share in the laughs. In addition to funny first date stories, I also think I’ve perfected the first date outfit by now.

My requirements in a first date outfit are this. It has to show a little skin while still being modest. We’re out here trying to trap a husband not a one night stand kind of guy! It also has to be cute without being too over the top. This is mainly because I don’t want to look like I tried too hard. We don’t want anything going to their heads after all 😛

There is a 99.9% chance you will find me in all black on a first date or if I’m going out for any occasion for that matter. Black is the most slimming and flattering color so of course us girls opt to wear it when we want to look our best! Now how formal the date is will determine how dressy your outfit should be. I always err on the more casual side. If you are going out for drinks, then jeans or a casual skirt are the way to go. If homeboy is ballsy/fancy enough to take you to dinner, you better pull out that LBD (little black dress) you’ve been saving up. For shoes, I almost always wear heels because they elongate your legs and well because your girl just needs an excuse to rock the absurd amount of heels that I own. But you do you girl. If the date location is outside, it is more than okay to wear sandals or flats.

First Date Outfits

Now for the first date stories! After writing them out, I realized how many bad first dates I’ve been on so I narrowed it down to the top 5 worst/funniest.

Crawfish King– I knew this wasn’t going to turn out well from the moment he asked me to go get crawfish. I mean not the sexiest first date peeling and sucking on crawdaddy’s. Definitely not my best look anyway. Between the awkward convo, him telling me he had no job and was depressed, and then getting mad at me when I politely told him I had to head home (after 4 hours) there was no second date.

Margarita Man– After telling him I hated Mexican food and margaritas he insisted on Papasitos. Besides the fact that something obviously got lost in translation, while on the date he told me that he goes to Papasitos every single day of the week for their happy hour and has 3 large margaritas. Alone. Thank you, next.

Sushi PTSD– As much as I love sushi I usually try to steer clear of it on first dates as it’s not the easiest, most ladylike food to maneuver on a first date. He picked a hole in the wall sushi place that I had never heard of. I almost suggested another place but 1) I didn’t want to offend him and 2) thought it might be a hidden gem despite the fact I’d never heard of it and I’ve lived in Houston my entire life. WRONG. We were the only ones in the entire place. The sushi was horrible and chewy. Later that night I experienced my first case of food poisoning.

Mr. Workaholic – Met this guy on Hinge and got together for drinks. He had his laptop out the entire time we were there. We had one drink, he walked me to my car and then went in for the kiss. I went in for the hug 😳

Baseball Boy– He took me out to the ballgame! He got so drunk that he kept falling asleep during the game. I think he snoozed for at least 3 innings. Funny part of the story is that I hit if off with another guy sitting next to me while Baseball Boy was sleeping and he ended up asking me for my number! #score

First Date Outfits