The Unedited Truth About Who You Should Pick When You’re Interested In Two People At Once


If you ever feel torn between two (or more) people, there are six questions you can ask yourself that can help make the right choice a little clearer. This is from my weekly podcast, “Heart of the Matter,” which you can catch on SoundCloud every Monday evening.

You’re deep in the dating game and not tied down to any one person. All of a sudden, you come to a crossroads where you have to (or want to) choose one person to commit to. Both people are great, and you can see yourself happy with either one, so how do you choose? These six questions can help.

1. Who does my heart lean towards?

You more than likely have two options: (a) go after the person with the highest probability of accepting your offer to become exclusive; or (b) go after the person who you want, but might not get.

Always choose the latter. Choose them every single time, and without hesitation.

If you settle with the “safer” option, you’ll always wonder, “What could’ve been?” had you pursed the person you really wanted. You could grow to resent them over time, which will only lead to them resenting you. In the end, everyone loses.

If you go after the person you’re drawn to out of the gate and it works out, obviously you’ll understand why that was the smart move. Even if it does not work out, you’ll feel better knowing that you at least took a shot. You will get over disappointment and heartache, but regret can last a lifetime.

2. Who do I get along with best?

Your significant other should be your best friend. If the only reason you’re drawn to someone is because of their physical appeal or what happens in the bedroom, the chances are it will never work out.

If you have a connection and chemistry with someone, and if you’re actually friends with them, odds are that relationship has a significantly higher chance of success.

3. Who do I think about first?

When you wake up, who is on your mind? Who do you want to text first? Who is running through your mind throughout the day? These things are often overlooked, for whatever reason.

4. Who do I see a future with?

Can far into the future do you see yourself with this person? Can you see yourself growing old with them, or would you be surprised if you make it to the summer?

You don’t need to decide right then and there if this is the person you’re going to marry, but there should be something about them and your connection together that should lead you to believe that this flame won’t burn out by the time the next season rolls around.

5. Who can I do absolutely nothing with?

This is arguably the most underrated question we should all ask ourselves. Life can’t always be one adventure after the next. A small percentage of people can afford (both professionally and financially) to do something new and exciting with regularity, but the average relationship will consist of relative downtime for the majority of the week.

What then? If you can’t enjoy someone’s company when you two are just watching TV, lying in bed, on a road trip, sitting on a bench at the park, or eating dinner at home, what does that say about your relationship?

Anyone can have fun during a night out or on a vacation, but you have to be able to enjoy each other outside of those situations. Eventually, your body won’t allow you to do the things you want to do.

6. Who do I trust the most?

And this is the most important question you should ask yourself. Whether it’s trusting they will do what they say they are going to do, or trusting them enough to be vulnerable and open up, you have to be able to rely on them.

Trust is the foundation of any successful relationship. Beware of people who have a tendency to be spiteful towards others or use others’ weaknesses against them. I don’t buy in to the, “But they’re not like that with me,” logic because it’s who they are. Even if they haven’t acted that way towards you yet, it’s in their nature to act that way.

If you can’t trust someone, there is no other good reason to pursue a relationship with them.