You can message back and forth all day long, but when it comes to an actual date, you have to put yourself out there. While the rom-coms make asking someone out look like second nature, we know there’s usually some anxiety involved. No shame.

Meet Match’s Dating Expert: Sylvi

With over 25 years in healthcare, Sylvi has dedicated her life to helping others. This passion eventually evolved from a focus on physical health to emotional health as she helps singles navigate relationships. Sylvi’s specialty is perfecting members’ profiles to attract who they’re looking for.

Q: How do I ask for a date without coming off as pushy or too eager?

A: Let your match know that you’re enjoying getting to know them and would like to meet up sometime soon. Ask them what their schedule is like. This confirms your interest in spending time with them and is a low-pressure invitation. It’s also a great way to feel out if the interest is mutual without making it awkward.

Q: I was turned down. What should I do?

A: We’ve all been there. If it’s clear that there will be no further contact, let them know that you appreciate their time and wish them well. If it’s a temporary situation – for example, your match is going out of town or has previous plans – ask again in a few days or sooner if your match brings it up. Life gets busy, so “no” doesn’t always mean never.

Q: My match accepted the date. Now how do I know who pays?

A: It’s 2021, so there’s no more hard-and-fast rules on who pays. However, if you initiated the date, be prepared to pay for both of you. If you didn’t initiate the date but feel strongly about paying or splitting the bill, feel free to let them know how you like to handle things beforehand. For example, you can work into the conversation, “I’m old school and pay for all of my dates. I hope that’s okay with you.” Or, “I know you asked me out, but I picked the restaurant, so can we split the bill this time?” If it doesn’t come up naturally and you feel strongly about paying, you can always excuse yourself to the bathroom and quietly take care of the check before returning.

Q: My last date didn’t look anything like their photos. How do I avoid this happening again?

A: Start by looking at your match’s photos and asking them to tell you about them. For example, if they have a lot of travel pictures, you can ask when they took those trips. Due to the pandemic, some photos may be over a year old. You can also look out for signs of discrepancy, such as obvious or heavy editing, super close headshots where you can’t see their entire face, and no full-body photos.

I also always recommend scheduling a Vibe Check prior to setting up a date. Video chats not only give you a chance to talk and see each other live, but can ease some of the anxiety that comes with meeting in person for the first time.­­