Before you ask your date if he wants exclusivity or loves playing the field, take some time to figure out what you want. Are you interested in dating only him, or are you asking because you want to keep meeting other people? How long would you be willing to wait for him to start being exclusive with you? Conversely, how many dates would you want to have before you would feel comfortable with couplehood? Knowing your answers before you ask him will help you to clarify what you want instead of rushing to meet his needs.

Dr. Young writes that this isn't a conversation to initiate when you're being intimate. "If you ask right after having sex or in the middle of making out, the response will be clouded by hormones." Instead, choose a time and place during the day when you have time to discuss your options. Consider how fast you’re moving with him as well. If you’ve only had one or two dates, it’s too soon to talk about being exclusive. But if you’ve been dating continuously for a month or more, it might be a good time to bring it up.

You might be afraid to be the one to ask because posing the question makes you feel vulnerable. Remember that standing up for your needs is an indication of strength, not weakness. Recognize potential feelings of insecurity, but don’t let those emotions overtake your conversation. The more confident you are in yourself, the less likely you are to base your self esteem on whether or not a guy wants to date you and only you. And the more secure you are in how you define your relationship with him, the less jealous or insecure you’ll feel. Having the conversation can actually calm your fears.

Make sure he knows you enjoy spending time with him before you launch into the question of how serious he is about you. If he understands that you’re asking because you care about the relationship, he’ll be more comfortable giving his answer. Listen to him fully before telling him what you want. If he isn’t sure that he wants to be exclusive yet, that’s valid, says Dr. Young. She recommends that you ask him to let you know when or if he does reach that point, and then wait. If he hasn’t said anything in a few weeks or months, but you still know what you want, ask him to commit again. But be willing to leave if your desires aren't compatible.