Let’s get you to the first date faster.

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.­­

How to make dating fun again

We get it. Dating can feel dull sometimes. Whether all your dates are starting to blend together, or you’re not even motivated to truly put yourself out there, it happens. This doesn’t have to be the norm though. Simply shaking up your routine can be exactly what it takes to bring back the excitement.

Match’s Dating Expert: Brooklyn

While mathematics is her specialty, Brooklyn knows there’s no one-size-fits-all formula for relationships. With this in mind, she’s made it her mission to help singles with their specific struggles, whether moving on from a previous relationship, or simply moving out of their comfort zone.

Q: I’m in a dinner date rut. How do I liven up my first dates while ensuring the other person is having fun too?

A: It’s easy to get caught in a revolving door of dinner dates. A new setting is what you need. While you’re still in the chatting phase, be sure to learn about your potential date’s hobbies, interests & even the activities they loved growing up. For example, if they used to play competitive sports, introduce some healthy competition with a round of mini golf. If they’re creative, consider a paint & sip class. Even if your date prefers a more traditional approach, moving that meal outside for a picnic or bringing takeout to a cool drive-in movie can make all the difference.

Q: When is a good time to start bringing my date on group outings?

A: I would suggest waiting until you’ve been on a few dates. It’s good to get in some quality one-on-one time together before introducing them to a group. However, if you’re someone who feels more secure meeting for the first time with friends, make sure you gauge your date’s comfort level first. After all, meeting your crew might feel a bit intimidating. Suggest they bring some of their friends along to ensure they feel more at ease.

Q: I’m out of my comfort zone now that I’m dating again. Any tips on how to overcome the anxiety & actually enjoy myself?

A: You’re not alone in this feeling. The majority of members are either new to online dating or getting back into the swing of things. Start by setting boundaries for yourself. If scrolling through tons of profiles is nerve-racking, set yourself a manageable time limit for how long you’ll sift through prospective matches each day. Maybe even reward yourself by doing something you love afterwards. If sending the first message makes you uneasy, compose a message template that allows you to customize the details depending on the person you’re reaching out to. And if it’s the actual in-person date that’s giving you the blues, consider setting up video dates to get better acquainted with them beforehand. The more comfortable you are, the more fun you’ll have.