How to Get a Second Date (On the First)

I’ll never forget the first-date I hoped would turn into more. I thought I did everything right. I showed up on time with flowers in hand. I made reservations at a swanky steakhouse (it turns out my date was vegan). Despite the dinner faux pas, we seemed to have a lovely evening, but in the end, I failed to ask for a second date. By the time I gathered the courage to text her again, time had caused things to fizzle.

Getting a second date is often difficult, at least in my experience. In fact, in my experience, it’s even harder than getting a first date. The pressure I put on myself to make a great first impression can make me focus a little too much on the first date and forget that (most of the time) I’d like to go on another one. 

All things considered, you can put your best foot forward when you apply a few common-sense techniques to dating. When I’ve tried these myself, I’ve managed to secure a second date every single time. So how do I make sure things go well?   

Keep these four tips in mind.

Dress like you’re invested

Many first dates are casual. You’ll probably look out of place in a three-piece suite at the aquarium. But you shouldn’t be afraid of dressing up a little bit. Think of your first date like an initial job interview — you want to advance to the next round, and that means making sure your ensemble is in line with the importance you’re putting on the occasion.

To make the best first impression, there’s a few fashion mistakes that I avoid. First, I skip sleeveless shirts and tank tops. Athletic wear can work, but you don’t want to look like you just finished a set of reps at the gym. Dress shoes and a jacket may be a little much, but I don’t like to wear sneakers. I wear some casual slip ons, instead. They can make relaxed formal outfits look more put together.

Women tend to enjoy a greater variety of fashion choices than men, so try to let your personality shine. If no outfit is speaking to you, dress the way you would for casual Friday at the office. Nice jeans and a fun blouse or a t-shirt work well paired with comfortable flats.  

Focus on your shared interests

It’s an hour in. You’ve already gone through the polite awkwardness of small talk. If you’re lucky, you might have really clicked. You know your date better now than you did before, and it’s crucial to keep up that momentum.

When the night is winding down, moving the conversation toward your shared interests will help you secure a future date. If you have a genre of music you both like, talk about live music – specifically, a restaurant or bar with live music that would make for a great second date locale. Find common ground and work with it. Football season is here, after all, so if you both love the Packers, suggest catching Sunday’s game at a local pub together.

Ask about their plans for the week ahead

Asking about your date’s upcoming plans shows that you’re genuinely interested in them. It’s also a good way to know how busy their life is. If they respond with something along the lines of, “I don’t have much going on this week,” you can feel confident about asking to meet up again.

Look into upcoming events

I may be somewhat biased because I live in Philadelphia, but if you do some research (Time Out has fun local options for more than 50 cities worldwide) you’ll usually find that there are plenty of creative date activities like independent movie screenings, outdoor concerts, or walking tours and wine tastings. The internet is packed with articles about ideas for second dates.

When the conversation reaches a point where suggesting future activities is appropriate, seize the moment. For example, if you’re discussing your favorite music groups and one of your dates’ top ten bands is coming to town, suggest grabbing tickets to the show.

Getting a second date

There’s no guarantee you’ll get to date number two. But you can save yourself some anxiety by paying attention to social cues and getting to know your potential partner — and by taking a chance and asking for a second night out before the first one ends.

Remember to be your best, charismatic self. Here’s to a second date more memorable than the first. As for the third, best of luck!

Content Survey (Inline)

We want to know what you think!