Unsure of how to get out there, or get back out there, this time around?
Unsure of how to actually get from the computer to the date?

June 23, 2016

Isn’t the point of going online to get offline?  (No need to answer that.  I think it’s pretty clear!)   So many people ask me, “How do you just get offline?!”  Or, “When is the appropriate time to ask someone you’ve met online out on a date?”  While there’s no one right answer, I’ll start by saying this: the sooner the better.

So, you’re having this great email exchange with someone online, but it seems to be leading nowhere, and, as much as I hate to say it, it’s probably leading nowhere because you haven’t led it anywhere!

You have a few options:

1.      Stop all communication. Clearly this person has no interest in meeting in person.

2.      Keep emailing until all of your hair goes gray.

3.      Suggest meeting in a casual, non-aggressive way.

No surprise here… the choice is #3: suggest meeting in a casual, non-aggressive way.  You might be tempted to just stop writing to someone when it doesn’t seem to be leading to a date, but here’s why I’ll tell you not to do that:

Assume ignorance. These people don’t know what they’re doing, either!  They have no idea when it’s appropriate to ask you out!  To drive the point home, this is one of the most common questions I get from my male clients: “When do I ask her out online?”  Give people the benefit of the doubt.  As a side note, in opposite sex relationships, women generally defer to the men to ask them out.  (I do advise women to do the asking, too, but on the whole, they are waiting for the men.)

Back to the question of when it’s appropriate to ask: anytime!  Let’s say you write to someone and he or she responds.  You could ask to meet in the very next message.  I’ve found that with my clients, there’s an 80% chance someone will say yes if he or she replied to your first message.  You’ve passed the “looks” barrier and the “first message” barrier.  You’re in.  And of the 20%, they may not have agreed to meet regardless of how many messages you’ve sent!  The odds are in your favor.  Use them.  In general, I recommend no more than six emails back and forth (three on each side) or a week of emailing before scheduling the date.

Now, how do you go about doing it?  Here are a few examples of how to ask someone out online in a casual, non-aggressive way:

“I’m really enjoying our conversation, and I think it would be nice (or fun) to continue it in person over a drink.”  Or “I have so many more things I’d love to ask you!  Maybe over a cup of coffee?”

But that’s just the start.  Then you have to pinpoint an actual day to go out.  Just asking vaguely doesn’t get you a date.  You have to ask specifically.  Add to the last line, “Are you in town this weekend?” or “How’s next Tuesday or Wednesday for you?”

Once you put the question out there, the other person has a few choices:

1.      Agree to the date you suggested.

2.      Propose another date.

3.      Answer your email but not respond to the part about going out.

4.      Not answer at all.

If the latter two, you no longer have to waste your time.  And if the former two, you have a date on the books.  Congratulations!

Now it’s time to get planning.  I do advise my male clients to choose a venue rather than leaving it to the woman because it adds so much pressure.  “What kind of place does he want?”  “Should it be near me or him?”  If he does leave the choice to the woman, though, then it’s her call!  If he objects to that, he can tell you.

Now, make sure you’re confirmed the day before.  There’s nothing more annoying than getting a date scheduled four or five days in advance and then wondering on the day of the date if it’s actually happening!  Rather than twiddling your thumbs all day waiting, just confirm.  You’ll save yourself time and annoyance.  Doing this over text is just fine.  And go with the positive, confident confirmation of “Looking forward to seeing you tomorrow at 7” versus the weak “Are we still on?”  It makes a big difference.

Then you have yourself a date, my friend.  Enjoy!

How to Take an Online Date Offline

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