3 Tips For Feeling Way More Confident When Asking To Define The Relationship

by Jamie Kravitz

As a goal-oriented 20-something, I always like to have a plan. I prefer things to be as organized as possible: I have an ongoing to do list on my phone, I try to keep my inbox at zero, and my small New York City apartment is relatively tidy. So when it comes to my romantic relationships, knowing exactly where I stand with someone is usually the goal. Unfortunately, I've never been as good at asking "What are we?" as I am at color-coding my bookshelf. When you feel like you're not confident enough yet to ask for a relationship, it can be easier to just "see what happens." But taking control of your love life is equally as important as maintaining a sense of sanity in your career and at home.

I spoke to two different life coaches about what to do if you want to define the relationship (DTR), but you're worried about being the one to open that door. They each gave a few helpful tips for navigating this understandably stressful situation, boosting your confidence, and ultimately getting up the nerve to ask someone you're seeing if the two of you can DTR. Here are three steps you should take, according to relationship experts.

Ask yourself why you don't feel confident about starting the DTR conversation.
Stocksy/Sergey Filimonov

"Ask yourself why you don't feel confident," says relationship and well being coach Shula Melamed, MA, MPH. "Is it because you aren't sure what you want out of the relationship? If so, take your time to really consider what you want and how you would like to continue this relationship. Is it because something doesn't feel right? If so, examine that feeling."

She says that if you sense this person might not be ready to take the next step, you should sit with your doubts and try to access your feelings. Listen to your gut — if you're hesitant to DTR, there may be a deeper reason beyond standard nerves.

Kali Rogers, CEO and founder of Blush Online Life Coaching and author of Conquering Your Quarter Life Crisis, also advises thinking about why you're scared to start the conversation. She says one possibility is that you don't feel like yourself in the relationship and subconsciously know it's not a good move for you. If that's the case, "dig deeper and reflect on whether or not you want to continue spending time with this person," she says.

Try not to think of the outcome in terms of being accepted or rejected.
Stocksy/Chelsea Victoria

Another worry potentially holding you back could be the fear of rejection. It's also possible that you're afraid of the opposite: that you'll be accepted. "Do a gut check," says Melamed. "Realizing you are worthy of a loving and connected relationship is a biggie."

She explains that more than being accepted or rejected, having the DTR talk is "about finding out if this relationship is going to be a place where you can grow and connect with this other person on a deeper level." Plus, it will let you know how this person handles emotional conversations, which is a good thing to know if you're planning to start a relationship with them.

If the issue has more to do with how you feel about yourself, though, it may be time to focus on you and your self-worth, according to Rogers. If you believe you don't deserve a relationship, that should be addressed. "Find a good therapist or life coach to help you through this process," says Rogers. "It's more important to have a healthy, strong relationship with yourself than it is with another person — so focus on that first."

Remember that you can't move forward (or move on) until you ask.
Stocksy/Jesse Morrow

Finally, remember that in order to get what you want (and deserve), you have to ask for it. The person may have no idea you're interested in a more serious commitment, simply because you haven't said so. And no matter how they respond, you'll be better off having a clear answer.

"If they decline a relationship and that's your end goal, then you are able to move on and not waste any more time in a dead-end relationship," says Rogers. "If the answer is yes, then you can move forward with peace of mind knowing you went for what you wanted and succeeded."

Asking someone to DTR isn't always easy, but the relief of finally having an answer is well worth it. No matter what the outcome, knowing that you advocated for yourself will give you even more confidence for the next big conversation.