There’s really no getting around it: First dates are super awkward. Even once you’ve brushed up on trendy online dating slang, found the *perfect* first-date outfit, AND picked a date night meal with the least probability of spillage, you’re still going to have to make awkward conversation with a stranger for an hour… without it turning into a bad game of 20 questions. In order to help us jump back into the dating pool with confidence, we asked five relationship experts for tips on keeping the conversation flowing naturally on an already-awkward first date.

1. Don’t skimp on the preparation. While planning out every detail of your date on color-coded flash cards may be too much, it never hurts to come with a plan (and having done some diligent Facebook stalking). “When I was dating, I would make sure I had several funny or interesting stories lined up to break the ice and make a good first impression,” says co-owner of Ex-Boyfriend Recovery Jennifer Seiter. “Bottom line: If you want your date to feel open and comfortable, come prepared.”

2. Plan something interactive. If you’re super worried about running out of things to talk about with your new crush, you may want to consider planning something interactive instead of a typical dinner and movie. “Dinner is nice, but when the bread runs out it can get awkward fast. A first date that’s an activity can solve this problem,” notes chief communications officer at Peoplelooker (AKA a background checker for online daters) Justin Lavelle. “For instance, try an Escape Room. The challenge to escape provides all the conversation you need. Regardless of success, working together is a great way to get to know each other.”

3. Ask questions that evoke feelings, passions, and stories. “Too often people dig for facts on first dates,” says certified counselor and relationship coach Jonathan Bennett. Instead of digging for answers about the childhood pets or quirky nicknames, Bennett suggests getting your date talking about their passions. “Most people are happy to talk about their passions but sometimes are too shy to take the lead,” he notes. “Asking questions that move the date beyond the usual fact sharing will help continue the conversation, build rapport, and create an instant bond.”

4. Take little risks. It may be easy to talk about safe topics and funny anecdotes all night, but don’t be afraid to take little risks to move the conversation toward something deeper. “Ask permission to either ask something a little more personal [about your date] or to share something a bit more personal about yourself and/or your background. See how they respond. If it’s positive, go for it,” says chief psychologist at Montefiore Medical Center Dr. Simon Rego.

5. Ask questions that matter to you. At the end of the day, you probably want to know if your date subscribes to any of your relationship deal breakers *before* you waste your time with a second date. Astroglide’s resident sexologist Dr. Jess O’Reilly reminds us that we’re totally allowed to ask these questions on a first date… no matter how awkward they are. “If you’re actually interested in the response (as opposed to simply asking questions to seem interesting or cultured), you’re more likely to generate rich and meaningful conversations.” In other words: Go for it, lady!

Do you have any tips to get through an awkward first date? Tweet us them by mentioning @BritandCo!

(Photos via Getty)