Milestones And Exits

There is a great episode of “How I Met Your Mother” (Season 2, Episode 12 “First Time In New York). It breaks down that in a relationship there are always exit points and milestones to avoid. Comedian and podcaster, Jared Freid, warns about vacations, birthdays, and holidays. If you are following the pattern of consistent dates and one of these scenarios come up….pay attention. Let’s break down some milestones and exits on the highway to love…..

Milestones In Time—



Three months…..

This is the first check-in- How is he treating you? Does he still make an effort to make you feel special?

Walls will come down and you will see his true nature- Up until now, he was trying to present his best self. Certain things might slip though the cracks as you spend more time together.

Your first fight- The question is, how was it handled? Did he fight fair or go for the jugular?

Has he called you his girlfriend- At the very least, have you had “the talk” and are on the same page?

Eight Months….

You actually know his friends- They know your name, know you are a couple. You have spent a lot of time in group settings. This step can happen very early on, but some guys like to hold out. This is the cut-off of knowing his friends.

Really look at his behavior in an objective way- Sit back and reflect. How do you feel around him? Do you feel comfortable and calm or does he always stress you out?

Ten Months…..

A lot of relationships end here- It’s not a year-long commitment, so it doesn’t come across as devastating if you break up. If he is acting weird around this time, he is at a crossroads.

One Year Plus…..

At this point you should know his full intentions- Best case is you will be talking about engagement depending on your age.

Hopefully you like his friends and family- this year isn’t about him choosing you, it’s about you deciding if he is a good fit.

Trust your gut- Make sure you are on the same page about children, where to live, and lifestyle. If you get a uh oh feeling, take note of it.

You have been to weddings, work events, and a weekend getaway- It’s understood you are his plus-one and have traveled together.

Exits In Events—



There will be certain events that come up when you know where he stands. Some are tiny, some are huge. In the first few months, it’s best to be observant of the effort he is putting in. The first step is keeping up with you on a consistent basis. Everything is easy when life is mundane then….boom…Christmas hits, or the dreaded Valentine’s Day….

The First “I will be out of town”….

This can happen at any point. You probably have gotten into a schedule of seeing each other fairly often. Then he needs to visit his grandma or go on a work trip. If a guy wants it to end or doesn’t want the responsibility of being a boyfriend, he will drop the ball. He won’t text or keep up with you.

The First “Back to school”….

If you are a summer fling, then anticipate it’s the end when school starts back up.

The First “Birthday”…..

Gifts, effort, quality time? All the love languages will be checked off. If it’s his birthday, it’s a red flag if he would rather spend it with friends.

The First “Holiday”…..

Even if it’s St. Patties Day, if he picks his friends over you, you might not be a serious as you thought.

The First “Second Date”…..

Anyone can go on one date. With the apps you can go on seven “first dates” a week. A true planned out second date (in public) is noteworthy.

The First “I am moving across the country for work, school, family”…..

I remember on the show “Friends” Chandler lied to Janice that he was moving just so he could escape her. I think about this a lot as far as meeting guys on the apps who live an hour away. Will they ever be willing to move for me or make it work? It is the biggest “nothing personal” excuse to break up and it’s used a lot when a guy can’t figure a way out.

The First “I got a raise or promotion and will be working more”…..

Again…nothing personal, can’t argue with it. If what he is saying is true, he might build up his ego to upgrade you for someone else. Depending on how drastic his money or status changes, it could be another lazy way to fade things out and get him out of the responsibility of doing nice things for you.

Bottom Line…..

Every relationship has little tests and exit strategies along the way. It is hard to find a way out when nothing is “wrong.” There are certain relationships that only last for a certain time period, such as a summer fling. I would say the first “out of town” tends to be overlooked. A lot of women will get on the excuse train and tell herself he is busy and x,y,z. A holiday, whether it is Halloween to Valentine’s Day will be obvious how he feels. It is easy to see each other when it is convenient. Pay attention to effort when obstacles get in the way.

Wanting The Relationship To Evolve

It can be frustrating if you have great chemistry, he treats you well, yet he doesn’t want to be your boyfriend. You begin to blame yourself and are convinced you are not girlfriend material. Most likely what happened was the relationship was rushed sexually and it became impossible to work backwards to get to know one another….

Can we avoid becoming casual in the first place?…..

How a relationship starts is so important! It’s easy to get in a pattern of going over to his place and hooking up. When you delay sex and insist of going on dates in public, you will avoid being stuck in limbo. It’s extremely hard to work backwards. If you already jumped the gun and slept together, see if he wants to scale things back. If he suggests dates in public and asks non-sexual questions about your life, you are on the right track.

You are always being tested…..

He might not have a clipboard on him, but he is constantly judging and testing you. When he brings you around his friends, that is the first test. Maybe you weren’t a great conversationalist with them and had your face in your phone.

What if you really catch feelings…..

If you are the type that gets easily attached to guys, then you need to pump the brakes at the beginning. Not every woman can do casual. Getting involved in an F-boy is the worst situation. Don’t accept bottom-of-the-barrel dates or send him nudes. Be firm about public dates. If he ghosts, then he was just after one thing. Get out sooner than later; he isn’t going to change his mind. You can waste years trying to impress a dude who doesn’t even know your college major.

Keep the “relationship” under wraps…..

The second you start talking to friends about how great he is, it will fall apart. Don’t glamorize or seek constant advice about him to your friends. Your bestie doesn’t want to see you hurt, however, her objections might “Romeo and Juliet” your attraction to him. Meaning, you will feel like it’s you and him against the world.

Can you turn it around and get serious?….

Hmmm….it’s hard. Men love murky and strive to be in a FWB situation for as long as you let him. He has probably put you in the hook-up bucket and cannot see you as more. If you don’t want to drop the hard ultimatum just yet, see what his actions are. Distance yourself a little and resist reaching out and texting. Pay attention to what he does on holidays and your birthday (if he even knows your birthday). He might be saying he wants to take you to a nice dinner, yet if you wind up only going to his place, then that was intentional. Actions speak louder than words in this case.

Keep dating people!….

Can’t stress this enough. A lot of the time a FWB will want to be exclusive. Yet it can be misinterpreted to mean boyfriend. It usually means he does not want you sleeping with other men. Do not agree to any form of exclusivity unless it is being boyfriend / girlfriend. In the meantime, keep going on dates, keep up with the apps. Don’t make him your entire world.

Bottom Line…..

If you are looking to get into a serious relationship, you have to do things differently. It involves patience and restraint. Resist having sex early on; it’s hard to work backwards to get to know a person. Don’t have the mindset, “whatever happens, happens.” You should be thinking of future consequences. Has a relationship ever formed based on a one-night stand?…sure, but you shouldn’t count on it happening and it’s not worth the risk. If you are just seeking casual and mean it, then great. You don’t have to force a casual guy to be your boyfriend. Just enjoy your time while you have it.