The First Date

Actually meeting the person you are talking to is one of the most important steps to online dating. That sounds amusing but many online daters dwell on internet communication overly long. I made this mistake early on and now understand why a few girls, after several emails, would ask direct questions like “Is there anything else you would like me to answer?”. They didn’t want to answer more questions! They wanted me to get the show on the road and they were right to feel that way.

There are times where you will feel like you are communicating with a “great catch” only to realize what a mistake that was 60 seconds into the first date. It is important to meet early on so less time is spent talking to the wrong person and more time is spent trying to find the right one.

When to Ask for the First Date

Sooner rather than later. The first date should be planned not long after communication has begun. It is personal preference on how long to wait but there are very few reasons to delay. After all, contacting someone is just a pre-cursor to the first date. It’s not as if you hoping to “chat” with someone and end it there. You want to talk with them and if things go well meet them.

One common reason to delay a first date is due to an attempt to learn more about the other person. This is not a very good reason. I found the first few minutes of the first date are worth more than dozens of emails.

Another reason to delay would be if the person you are communicating with has expressed extreme reservations about meeting people from the internet. I once talked to a woman for two months before we met. She was very nice and we got along well so I was willing to communicate but let her know I’d be talking to others while she gained comfort. This reason is acceptable, especially considering the hassle that some women end up going through when dating online.

Photo by Michel Filion

In general, my rule is an invitation to meet should come by the third email you send. By this point you have talked back and forth twice and can measure how well you are getting along. You will be able to judge the situation better as you communicate: sometimes you’ll get a date on your first email, other times you may realize a few weeks of communication would be best.

I found that people will not be offended if you suggest a first date before they are ready. In my experience, the other person would offer an excuse but continue communicating. If this happens to you, wait a few days (continuing the email conversations) and then ask again.

Unless a good reason is give for not meeting, I would not ask more than three times – there are some people out there who are looking to make online friends or live fantasies out in their head without any intention of actually meeting. Other times, people are just reluctant to meet you because they are still trying to decide if they like you. After a while, any of these cases is a waste of your time. A grown woman (or man if the lady is asking) can decide in a few weeks if she would like to meet you – someone looking for a pen pal should do so somewhere else. Your time is valuable and should be used to communicate with people truly interested in meeting you.

What about the Phone?

I never went for phone conversations as a stepping stone from internet communication to meeting. I tried phone conversations early on but had a few bad experiences with “excessive calling” and one case where a girl took it as a personal offense every time I had to get off the phone.

Photo by e3000

Honestly, I have never felt comfortable talking on the phone for long periods of time (even to close friends) so I prefer to jump straight from the internet communication to meeting. If you enjoy talking on the phone or prefer to do so before meeting someone, treat this step like you would the first date by asking for the phone number by the third email. If you really hit it off on the phone (for example, did you talk for two hours without even realizing it?) ask for a first date as soon as possible.

Regardless of the success of the first phone call, I still think the first date should come rapidly so don’t wait too long to move from phone conversations to a real meeting.

First Date Length

Plan to keep the first date short. Hint or specifically state that you can only be out until a certain time. Most people will accept this or make a joke in an attempt to fish for more information (“What, have another hot date after ours?” was the most common for me to hear). You can come up with a reason you can only be out for a set amount of time but most people will not press very hard to find out why.

Limiting the time of the first date is a safety precaution: if you end up on a nightmare of a date you’ve already established your “out”. If on the other hand the date is going excellent, suggest to your date that you extend it. Your date might remind you of your time constraint (“But I thought you needed to be home at 8…”). If so, tell the truth. People who are dating online actively will appreciate your planning for a bad date and like the fact that you are saying to them “this is a good date”.

If you would rather not let them in on your planning for the worst-date-scenario, just say that you’d prefer to cancel your previous plans and spend your evening with them. Either way you approach it, they won’t mind if they are having a good time. If they insist you not break your plans you may want to evaluate how well the date is going!

On my first date with my wife, I schedule a one hour date at a diner. After the hour was over, I explained that I only extend the good dates and since ours was a great date asked if she would be up for miniature golf (she was). In contrast, many times the dates ended with coffee or lunch. This approach is a cousin to the having-your-friend-call-you-and-faking-an-emergency act that some people think is so slick. I think planning ahead and bowing out gracefully is a much classier approach.

First Date Locations

The first date should be about each of you learning about the other so there should be as little distraction as possible. Coffee shops, bookstores, restaurants, parks, and bars (that aren’t too loud) will all provide a good place to meet where the object of attention is each other. A baseball game or a museum isn’t too bad but I think each makes for a better second or third date. As always, listen to your gut. If you both establish you love ballroom dancing before meeting, you obviously have a very good non-traditional alternative.

There are no rules written in stone but for your first date keep it simple and make sure you go somewhere where you can hear each other! If you can only function properly on a date after you’ve had a drink the bar is fine but try to select one where you’ll still be able to hear each other speak.

Movies are the worst first date idea in my opinion. I have some friends who like movies on the first date because “it gives them time where they don’t have to talk”. Well, I really do understand what they mean but they’re going to have to talk to the person someday! If it’s not easy from the start I find it difficult to believe that watching a movie is going to make the conversations flow much better. Oh, sure, you can talk about the movie afterward but that can only last so long.

I settled on coffee shops and bookstores for most of my first dates. I found many of the other options were hard on my bank account, especially once I started going on multiple dates a week. I also found that women were very open to meeting for coffee (even when they didn’t drink coffee) because of how “safe” this type of date was.

Interested in Learning More on First Dates with Online Dating?
In this article I’ve discussed many of the ways to prepare for your first date…but there is far more to discuss than what has been described here. Below is a list of several other articles that I hope would help you as you begin to meet singles with online dating:

• Mentally Preparing for the First Date: In this article I discuss some of the challenges of first dates and offer recommendations for how prepare and then handle dating set-backs.
• First Date Conversations: A breakdown of different type of conversations you can have on your dates (and often should be having as you meet new people)
• First Date Questions and Conversation Starters: A simple list of topics you can review to help get the conversations going.

Alternately, you can check out my online dating guide which includes these topics and much, much more on all major areas of online dating.