You only get one chance to make a first impression. Make it a good one! Read on for tips on what to wear, what to bring, and what to talk about on a first date.

What to Wear

  • Accurately represent yourself as much as possible. Don’t “dress to the nines” if that’s not what you usually do. However, I don’t recommend wearing sweats, even if that’s what you usually wear. Look like you made some effort. Comb your hair, apply makeup (if that’s what you usually do), and put some thought into your outfit. I almost always lean toward nice, dark designer jeans for every first date. (Joe’s Jeans fit me best, so I stick with that brand.) I feel most comfortable in jeans, and they can be dressed up or down. I add a cute top, a belt, jewelry, and appropriate shoes. I touch up my makeup and make sure my hair is still presentable, sometimes adding a cute barrette. I prefer to keep the focus on me and my charming personality, not on my clothing.
  • Dress appropriately for the venue. Although I usually stick with jeans, top and shoe choices change depending upon venue. If I’m meeting my date in a park on a warm day, I’ll wear sandals and a nice t-shirt. If I’m going to a museum, I’ll wear a nice top and comfortable shoes… like my cute yellow flats. If I’m meeting in a bar, I’ll wear a dressy top with heels or dressy pointed-toe flats. Use common sense. For example, don’t wear heels to park.

What to Bring

  • Cash or credit card. Always be prepared to pay for your half of the date.
  • Identification. This is a no-brainer, especially if you’ll be using a credit card or drinking anything alcoholic.
  • Anything else you might need for the venue. Ideas: Sunblock, water, medication. My ex-husband, Mars, once said he went hiking on a first date. His date was asthmatic and forgot her inhaler. She had an asthma attack on the trail. Stupid. Needless to say, there was no second date.

What to Talk About

Most conversation flows naturally and easily but if your date isn’t being very social or engaging, you may have to get creative. Here are some ideas to get you started:


Did I forget anything?

What do you usually wear on first dates?