Schedule Your Dates Like a Pro!

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

Simplicity is key.

Here are 5 tips you can apply to have your man sitting next to you on your next date.

1. Be Prepared

Go into your date “scheduling conversation” with a possible plan for a good date. Pick something considered 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. Try to 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 thought of a fun date suggestion and can throw it into the conversation. Suggest the date you’re 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

Try to schedule a date ideally within 3-5 days. Some guys have a hard time scheduling dates too far out in advance. While he may agree to that Thursday night at the end of two weeks from now, he might not really know if he has any plans already scheduled for that night or if there is a favourite game on TV that he would have loved to watch. Involve him 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, fun conversation before getting into the details of scheduling. The flirting part shouldn’t be so extensive that you never get around to the scheduling part, 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. 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 and says something like ‘I will catch you soon”, then you might want to consider it a red – or at minimum – a yellow flag.

4. Leverage your phone

Here is my strong advice: You should have at least one phone conversation before your date. Emailing can take you gracefully into the beginning part of getting to know him (many people often can open up more when there is a little ‘anonymity” which email can offer) but it is important for the two of you 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 (done by email or text), always try to end your phone conversation with the date info once again for clarity.

5. The plus side of texting

Texting is no longer just for teenagers. Men are becoming the most prolific texters and often use it to communicate between their buddies much more than using the phone. But men tell me all the time that women try to use texting for complicated conversations. Don’t. Keep your texting short and sassy when you are communicating with guys. They will respond much better! A simple text of “Hi – what’s up? Got plans for tomorrow night?” could be all you need to get things started.

I also suggest texting 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 “all 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, and he will want to schedule that next date soon!!