Dating Fun: Schedule a Date Like a Pro

Scheduling fun dates seems to have become increasingly more difficult for the women I coach on how to have dating fun. One of the recurring questions I am asked is “how do I get my dates scheduled with less hassle and more ease”?

The key is to keep it simple. If a guy is more hesitant than you anticipated about scheduling a date, it is not necessarily a red flag. The man isn’t trying to offend or show disinterest in you, it’s just the way he has learned to operate with women. Your role is to smoothly break this hesitation – a little flirting should do the trick. Try to chat with the guy and remind him why he was interested in the first place. Here are 5 tips you can apply to have your man sitting next to you on your next fun date.

1. Be prepared. Go into your date “scheduling conversation” with a possible plan for a good date. Pick something safe (maybe not the opera or a museum) that is simple to plan and will be enjoyable for both of you. But, don’t throw the plan at him right away. Casually move the conversation to discussing possible dates. A guy that is really on the ball will, and hopefully should, have some ideas of his own to offer if he wants to see you. If he seems to be unable to offer a suggestion for a date though, you will already have a fun date suggestion in mind and can throw it into the conversation. Suggest the date your thinking of and see his reaction to it. If you picked something that is fun for both of you he should be willing to take part.

2. The sooner the better. Some guys have a hard time scheduling dates too far out in advance. While he may agree to that night end of next week, he probably has no idea if he has any plans on that night. Try to schedule a date ideally within 3-5 days. Involve the man in the date scheduling. Be sure to ask for his input, but just make sure that by the end of your conversation that you actually have a date on your calendar that you are confident will work out. You shouldn’t be saying “I’ll see you on January 1st”, rather “I’ll see you this Wednesday night”.

3. Use your words wisely. The scheduling of your dates is unlikely to be done in person. Instead the interaction these days usually occurs via voice and/or text. This means that the only things connecting you and the man are the words you choose to speak. Be flirty, yet firm. Remind him how interested he is in you. Enamor him with a sprinkle of light conversation before getting into the details of scheduling. The flirting part shouldn’t be too tough, but it’s important to be firm in the aspect of scheduling so it doesn’t get into a long negotiation. Discuss your options of possible things to do and when to do them, and then reach a conclusion. A conclusion about the upcoming date is imperative to it actually happening. Remember, don’t let the conversation end before restating the date information (day of the week, time, place). If he truly won’t commit to moving your interaction forward, then you might want to consider it a red (or at minimum) a yellow flag.

4. Leverage your phone. You should have at least one phone conversation before your date. Texting and emailing can take you so far, but it is important to actually speak and to establish a true connection. So whether the phone call is partly to schedule the date or it comes after the initial scheduling, always try to end your conversation with the date info for clarity.

5. The plus side of texting. Try to keep texting on the flirty side of the spectrum by having light and easygoing conversations. A simple text of “Are you doing anything tomorrow night?” could be all you need to get things started. Or text maybe a couple of hours before you are scheduled to meet just to confirm you are on your way/on time (something simple and flirty like “life is good from my end and I’m on time- c u soon”. That way if any issues do come up at the last minute, there is a means of open communication to deal with them. In today’s day and age, everyone relies on their phone!

The best advice for getting a man to be more committed to dating and not being hesitant to schedule dates is to actually have fun on your dates. So don’t fret if you have a bit of back and forth in scheduling a date. If you and your man have a great time, there’s a good chance both of you will want to try it again. Because you are so much fun, he will want to spend more time with you.

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