Relationships
The "8-Date" Checklist Will Help You Gauge Compatibility
Think beyond a coffee hang.

While fancy dinner dates are nice, there’s only so much you can learn about a person over a glass of wine and a bread basket. At some point, you’ll need to venture out for mini golf or a movie, to see what it feels like to coexist in a different setting.
In fact, many relationship experts recommend going on a variety of dates well before you make things official. There’s even a viral “eight date” checklist you can follow to ensure you cover all your bases.
Instead of grabbing coffee each time, for example, it suggests planning an adventurous date, a fancy night out, a group hang, a last-minute activity, an errand or chill day, a weekend getaway, or a date for a deep conversation. Once you have all of these experiences under your belt, it should be easier to tell if you’re a good match.
While it’s fine to start with the classics at first, Sharon Kwan, LCSW, a psychotherapist and founder of Bodhi Aware Therapy, says it helps to branch out soon after as a way to get to know your partner better. Here’s why the eight-date checklist is a good idea, as well as how to follow it.
The “8 Date” Checklist
As Kwan explains, it’s hard to test your compatibility with someone when you’re just doing the same thing over and over again together. “You need to witness them at their highs and lows, identify their strength and weaknesses, and your similarities and differences,” she tells Bustle. “Otherwise, you're not really getting the full picture.”
1. Casual Coffee Date
The casual coffee or drink date is a good go-to for your first hangout. It’s easy, and it also allows you to see how the conversation feels. Does it flow? Is there banter? Do you feel like they’re listening? This is the time to gauge the basics.
2. Activity Date
Next, try an adventure or activity date, which could mean biking, kayaking, bowling, or puzzling your way out of an escape room. “This is your chance to test whether your values are aligned and how each person feels about risk,” Kwan says. If adventure is important to you, you’ll want to make sure your partner is happy to hop on a bicycle.
More importantly, it lets you see how they handle competition, as well as how well you work together as a team. Are you able to successfully row a canoe across a lake without arguing or falling in? If so, it could be a good sign.
3. Fancy Dinner Date
The fancy dinner allows you to see your potential SO all dolled up, and according to Kwan, that can be an ideal test for physical attraction. An evening at a nice restaurant also gives you the chance to double-check their manners (or lack thereof). In a way, it can even reveal if you’re both on the same page. If they’re invested, they’ll be more than happy to admire you in the candlelight.
4. Group Hangout
Kwan notes this is one of the most valuable dates to gauge a relationship’s potential. “It's a chance for you to see what your prospective partner is like with their friends,” she says. “Do they behave the same way with them as they do with you?” If their personality doesn’t drastically change, it’s a green flag.
The group hangout also allows you to see if you like who they surround themselves with, and vice versa. Invite them to gather at a bar or plan a casual party so everyone can mingle. If your friend groups get along, feel free to start planning your future.
5. Spontaneous Date
Consider what would happen if you called them last-minute and asked them to meet you at the movies. “Excitement and mystery are big tenets in making those early months of a relationship memorable,” says Kwan. “It helps keep the spark alive and helps you understand what a person's comfort zone is — and isn't.”
Spontaneous hangs let you judge their flexibility, too. Can they go with the flow? If not, does their desire to plan ahead complement your Type B personality? According to Kwan, it’s OK if you’re opposites, but it’ll be good to know that before you make any major commitments.
6. Errand Day
As you get further into your relationship, make sure you spend at least one chill day together, either doing nothing or doing something super normal, like running errands. “This is where you really get a glimpse into what everyday life would be like,” she says. If it’s fun to run to the bank together, you might be a match.
7. Weekend Getaway
“Traveling together for the first time can tell you a lot about a person,” says Kwan. Not only is it an exciting way to make memories, but it’s also a chance to test your travel styles and witness your potential partner outside their comfort zone.
Do they handle stress well? Are these easy to travel with? Or are they hangry the whole time and mad about the traffic? “It also allows you to really spend time doing nothing together, whether it's driving and listening to music or waiting at the airport,” she adds. “How does it feel just sitting and being by this person?”
8. Deep Conversation Date
This one might happen over coffee, in a park, or while lying next to each other in bed — and according to Kwan, it could be the make-it-or-break-it point. This is when you’ll double-check your values to see if they’re aligned, as well as talk about what you both want for the future.
The deep convo could also be the right time to open up about your past or share something deeply personal that you’d want a future partner to know. See how it feels to be honest and real, and also take note of how your info is received. If you can both handle what you hear, and you still feel comfortable and supported, you have better potential.
Planning The 8 Dates
While these dates may unfold naturally, you can also take it upon yourself to plan them, especially if you’re on your ninth hang and still haven’t ventured beyond the bar.
Kwan’s tip? Be chill when bringing up different date ideas. “Make it a conversation and event that you can think about and plan together,” she says. Remember, this eight-date rule isn’t a test or a “gotcha” moment, but a way to try something new and see what happens.
Once you experience each other in other in a variety of settings, you should have a better idea of your compatibility, making it easier to know if you should take things to the next level.
Source:
Sharon Kwan, LCSW, psychotherapist, founder of Bodhi Aware Therapy