Almost everyone is nervous and unsure about asking for a second date. Should you send some hints or ask directly or should you try to corner him or wait for him to ask you?

Assertiveness behavior involves taking the initiative, rather than waiting for something to happen. If you don’t say anything, probably nothing is what you’ll get. And if you handle the situation in a more assertive way, the other person will respect you not just for asking but for being proactive.

Here are some guidelines for handling this difficult situation. Every man or woman is different and may require some adjustment:

1. Think assertively, act assertively from the start. If you think oh! I am really a strong person once he or she gets to know me that day will most likely never come. You will never make it to the second or third date.

2. Introduce the subject subtly and slowly. Throughout the date, ask questions like, “What’s your typical day like?” And if he or she seems to have a busy schedule, ask casually, “Do you ever have any free days during the week?”

3. When you’re saying goodbye, you could also say, “Let me give you my cell number in case we can’t meet.” Give your number, and then ask, “Do you have a cell number?”

4. If the date goes well, don’t wait for the other person to call you, let them know you had a good time. Call him that night if possible just tell him you had a good time. If your date also enjoyed some quality time, you’re one step ahead.

5. Keep the phone call short. Don’t undo the positive impression you’ve managed to create by holding on to the line.

6. Depending on your trust level, give him a call to see if he would be interested in meeting again. The most confident people usually don’t mind calling the next day because they are confident that they made a good impression and the person will most likely want to see them again. If you are in doubt about whether or not he or she is attracted to you, you may want to wait a reasonable amount of time (two or three days) before calling.

7. Be short, clear and specific: “Would you like to go on another date with me? Or “Would you like to play tennis on Thursday? That would be fun!” or “I volunteer at Children’s Hospital on Saturdays. I’d like you to come with me.” Asking this way is usually assertive but also non-threatening and respectful.

8. Don’t expect the other person to give you an answer right away. He or she may want to think about it or check her schedule. If he or she says no (his or her right) nothing is lost or hurt if you ask assertively.

9. Don’t apologize for asking. If you respect other people’s right to say “no” and don’t see it as a personal attempt to demean or reduce your value in any way, then it will be easier for you to ask without fear of rejection.

The focus of assertive dating is to balance relationships, not control them; earning self-esteem, not the approval of others; possessing “power to”, not “power over”.

See also

Assertive dating: how not to act like a loser every time

Assertive dating: how to get more respect?

Assertive dating – how do you make sure you are connecting with your date?

Assertive dating: how do you tell him or her that you want more?