How to handle the awkward, total fun-suck of second dates

by Erin Brandt

A successful first date can be a great ego boost but, how do you move from the first date to the second date? Where do you “go” for that second date? When do you call or text after the first date? And how the fuck do you manage all of this in the middle of a pandemic?

There is a misconception that a game must be played before reaching out to someone you are interested in — waiting a certain amount of time or acting nonchalant when you are well and truly interested. Skip the game-play and focus on communicating your interest for a second date. COVID not only screws up the logistics of dating it also makes what could have been a more chill process seem urgent. No time to mess around with quarantine or serious illness a possibility at any moment. Call/text/carrier pigeon a message as soon as you can. Let them know that the first date was (insert adjective here) and you can’t wait to see them again soon.

In this day and age, texting is a popular way of communicating but I am going to encourage you to call the person you are interested in and make the connection with your voice. Personalizing communication is important in the initial stages of dating to build intimacy and there is no better way than speaking to each other and spending time together—even if that time is on a Zoom date.

What makes a great second date? Hopefully, you will have picked up on some shared interests during the conversations on your first date. Maybe a shared love of seafood or everyone is a champion mini-golfer. Maybe there is a new art installation you both want to see or now you have someone to go hiking/skiing/skydiving with. Whatever activity or activities you choose for the second date, use the opportunity to build on connections made in the first and share new pieces of yourselves.

Second dates are traditionally longer than a first date and are likely used to spend time doing something you share in common. You know I’m not big on tradition so definitely, try something new, fun, out-of-the-box. Some people will need a second date to be an extension of the first date so they can get to know the person better. Others will feel like the second date is more like the fourth or fifth and will use the time to make a deeper connection. Whether you go back to the first date coffee house or you spend 2 hours on Zoom talking about life, goals, work, or family — you both benefit in communicating about how you want to spend the time.

The first date was awesome.

You felt really connected and spent the whole time talking about yourselves.

A second date is excitedly scheduled and anxiously awaited.

You meet up and silence ensues.

It seems as though the first date sucked all the fun out of the second date. Or, horror-of-horrors, the second date includes an activity neither of you ends up liking, e.g. whale watching that includes a discovery of seasickness, no whales, and the worst weather imaginable. How do you move forward on a second date when doubts or mishaps abound?

One of my favorite movies, “Three to Tango,” includes a really bad food poisoning scene that by the end of the film the characters have bonded over. Mishaps during a date can actually bring you closer together if you can move past the bad parts and laugh about it.

If you are dealing with silence or awkwardness, humor can lighten the mood. Joke about how strange it is that the first date was so great and now you all seem stuck.

Making fun of a situation helps to make it seem less serious or less like a failing moment. The great part about dating is that you really have nothing to lose. The people you are seeing are not yet a big part of your life and the world will not end if it doesn’t work out.

Each date goes from great to awesome or you laugh at disasters and decide you want to try again. The key to moving from one date to the next is to talk to each other, honestly, about how you think things are going. Either of you may decide that you have more fun as friends and that any initial attraction was fleeting. Or you may end up with hot and heavy sex after every date. It is important to be clear from the beginning how you are feeling so that you do not reach a point where date number twenty includes someone having strong feelings while others feel like you are friends. By communicating honestly from the get-go, you can enjoy the situation with a clear head and establish a precedent in the relationship for honesty about feelings.

A third date or any future dates are perfect opportunities to share with each other interests you may not have in common. I talked a lot about making connections through shared interests but you will not share everything, which is valuable in a relationship.

You do not want to date people exactly like yourself, so celebrate any differences. If you are trying out something that is new to you because it is something loved by your date, do what my partner and I do—have a no-thank-you bite by trying it and knowing it is OK to say, “No thanks!” if you don’t like it. For example, if you are doing something physical together make sure you put a cap on the amount of time; so a thirty-minute hike instead of four hours. This way if the activity isn’t going well you aren’t deep in the backcountry wishing you weren’t stuck on this terrible date. Instead, you can move onto the next activity or end the date then.

There are so many options for things to do together, but first, you have to make the phone call that will set up another date! With the pandemic, use your creative side to connect without being in the same room. Here are a few suggestions:

• Zoom (or other video call software) while sharing a meal

• Write snail mail letters for the first month

• Set a challenge to record yourselves doing one or two activities you love and then share the videos

Try something new or stick with something comfortable. Don’t forget to be honest about your feelings and remember to laugh! Dating is a free pass to fully be yourself because you will attract friends, lovers, and partners who appreciate the truest version of you — you have nothing to lose.

Erin Brandt (she/her/hers) has been a sexologist for 15 years. When she’s not spreading sexual knowledge, Erin can be found learning from her child, hiking with her partner, cuddling with her pitbull, knitting with her cat, dancing with friends, and searching for the nearest hammock and ocean breeze. Want more? Visit


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