There’s a shaky line in dating between how many dates a week are appropriate and when the word dating no longer seems appropriate. If you ask me, the limit does not exist, especially when the chemistry has rolling bubbles. But take the latter to its extremity and all we’re left with is a pen pal. Planning a date between two people can be tricky. There’s always someone out of town or slammed with work. Picking a day and time that works for two people is genuinely the ultimate struggle of our generation. 

We’ve got people to see and things to do or we simply can’t be bothered to do anything at all. However, it’s our generation’s can’t be bothered to do anything at all that poisons a dating dynamic. Without the existence of plain initiative, the relationship is no further on than your high school crushes. 

As plans dissipate because of uncontrollable external factors, traveling, visitors, work, etc., the race to avoid being pen pals is on. How long is too long before we’re able to see each other again? How long is texting enough? For this, Lindsay was wrong. There’s a limit. Do we all have the same one? No, but everyone deserves better than a pen pal.

When schedules get dicey, each person needs to put extra effort into making a date plan. There’s compromise and the simple showing of interest in the other person. Questions of availability are asked, times and days are suggested, and a place is discussed, ending with a mark on the calendar with a date. Except, sometimes even with a recipe as easy as this, there are still terrible cooks out there. A poor cook with a laziness problem. 

At this point in the dating stage, the struggle with timetables is the moment of truth. What is their level of interest in the relationship? Dating is simple. People will make a date happen if they want to. If they want to pursue you, they will. If they are too scared to try, then they should work on their inner confidence and try back again later… only if the offer still stands. 

We all have different expectations for how many times a week or month we want to see someone we are dating. Yet, there’s one thing we all don’t deserve. Being someone’s pen pal. It’s important to understand the signs to avoid a Marty from Greece moment. We are Marty for Halloween, but our Rolodex is filled with experiences, not pictures of dates that never showed initiative. 

Here are the signs you may be becoming pen pals…

• They ask you when you are free, but never follow through with a plan. (After you’ve shared your availability)

• Text discussions of “we should see that” or “we should go there together” never reach reality.

• Plans are only based on running into one another at a bar or place.

• They arrange no plans at all (after the first meeting). Texting without a date IRL in sight. 

Is the frustration of never seeing the person we’re “dating” worth the texting? New York City, including all five boroughs, is only 35 miles long. And the city is full of date possibilities with various activity lengths. If they aren’t available for a ten-minute walk in a park with a corner cart coffee, then maybe they aren’t worth the finger pain. 

Being someone’s pen pal in the same city isn’t why we are strumming through dating apps. A date is an opportunity to learn and try new things. We all deserve to experience just that. There’s nothing wrong with telling the other person that you want to go on more dates. When it comes to building a relationship of any level, being pen pals doesn’t cut it.

No initiative to make a date? No picture in our Rolodex. 

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