When You're Not Sure If You Should Keep Dating...

Have you ever been in the awkward dating phase where you’re not sure whether to keep dating or if you should call it quits? This can happen to a lot of people early on in the dating game. Maybe you’re doing phone call after phone call, or you’ve been on one or two dates, or maybe it’s been a few months of going out. Perhaps you’re even exclusive, but you’re second-guessing your decision. What’s a good Catholic to do?!

The solution is actually quite simple. VERY simple. There is a two-step process that will solve all your not-sure-what-to-do woes! It is:

1. Assign an expiration date. 
2. When that date hits, you DO NOT break up! You have a serious discussion with the other person about where this relationship is going.

Let’s go over these two steps in detail. There are very specific reasons and benefits to these steps, and committing to doing them will steer you in the right direction no matter your situation.

Assigning an expiration date.

You don’t even have to be talking to someone to do this! The goal is to know how long you personally feel comfortable staying in a lukewarm dating situation–even theoretically. This can be different for everyone because every person is unique and individual. Think about yourself, your life, your personality, your personal boundaries, and decide when your timer “buzzes out.” How do you do that? Start by asking yourself these questions:

• Am I an impulsive person, or do I hesitate before making decisions?
• Do I struggle with committing to things, or am I confident in pursuing what I want?
• Am I looking for a specific type of person, or am I open-minded about dates? 
• How soon do I feel a spark, or know if there isn’t one?
• How well do I want to know someone before becoming exclusive? 
• Am I comfortable with past romantic choices, or are there things I need to work on?
• What do my trusted friends and family recommend for me?

The answers should give you a strong idea of when a so-so romance hits your expiration date. And ta-da! This time frame is your window of romantic opportunity. This is how long you can safely invest in someone before determining whether you should pursue this relationship much more seriously. Your expiration date might be a few weeks after meeting someone, or it could be six months. (If you’re really unsure, my rule of thumb is to go with three months and adjust as needed. This offers enough time to get to know each other, and also prevents unnecessary lollygagging.)  And it’s totally fine if the person you’re dating has a different timeline than you do. Whoever hits their personal “expiration date” first will move you both into step two.

Sitting down and having a serious discussion about the relationship.

Why do you have to do this instead of just ditching the relationship when it “expires?” I’m glad you asked. First, you really can’t know what the other person thinks until you talk about it. Second, airing all the concerns and answering each others’ questions is the only way to make an informed decision whether to break up or stay together. And third, this offers you the invaluable chance to gain clarity and learn from the situation. Everyone prefers closure to ghosting!

Okay, moving on to the actual serious discussion. At this point, tell your lukewarm date you need to talk to them about this relationship. It’s great to do it in person, but it’s also fine to talk on the phone or on video chat about this. Avoid texting or messaging because it’s impersonal and a misunderstanding is bound to occur. (If the person ghosts you and never replies to your request, this sucks; but consider them a bullet dodged!) So you sit down over coffee and tackle the tough elephant in the room. How do you bring this up? What do you ask? What do you say? Try these:

• So we’ve been dating for a while, and I want to be totally honest: I’m not sure how I feel about us as a couple. What are you thinking?
• It’s been about three months since we started talking (or whatever your timeline is.) I know myself, and I feel it’s time to decide whether we start dating seriously, or say goodbye. What’s your gut reaction?
• I’m going to cut right to the chase. Do you want to keep dating or not, and why?
• Don’t worry, I’m not trying to dump you right now. I’d like to really dig into whether we’re a good couple together, or if we should consider seeing other people. Thoughts?

If there’s anything specific that has been concerning you, bring it up now. (For instance, an ex-date of mine was worried I wasn’t attracted to him physically; he was right, but I was dumb enough to not realize it until he said so!) Be kind, be honest, and most of all, listen to the other person. If you’re like me, you might just have a pessimistic view of the relationship, and the other will help you see it with a better view!

Making your decision.

The whole point of having this uncomfortable conversation is to make an informed dating decision afterward. Now, don’t feel pressured to decide as soon as the bill is brought to your table! Sometimes, of course, the other person will decide immediately or even storm out on you. (Again, this sucks, but said bullet is dodged.) But if they don’t, suggest you both sleep on it. Take the weekend to consider your discussion, bring it to God in prayer, and consult with your trusted best friend or family members if you want. But make it your goal to make a calm, amicable decision. Respect the other person’s opinions and decisions, and if you are going to break up, do your best to be civil. It is important to be clear, concise, and kind during the breakup.

And who knows, you might flip this coin to heads instead of tails! It’s possible your concerns are unfounded, your hesitation will be reassured, or your worries will be soothed during this conversation. You might discover new things about each other or learn something which puts a whole new perspective on your relationship. You might be a great match after all! And if so, aren’t you glad you followed this two-step process? (You’re welcome!)

Now get out there, newly armed to battle situationships however they may come!