Online dating emails: Your questions answered

In my line of work—date coaching—I get all kinds of questions, ranging from how to contact someone before the date to when it's appropriate to call yourselves exclusive… and everything in between.  Many of these questions revolve around the emailing process on the various online dating sites.  Let's take a peek at some of them:

Question: Some of the emails are obvious that I will not be answering, but I'm wondering what I should do about winks and the emails that are not so obvious what to do with.  For example, several guys wrote something to the effect of this: "You seem interesting. Write me."  How do you recommend that I handle those?

~ Janie, 41, Cherry Hill, NJ

Answer: To answer your question, for the ones who either wink or write short messages, it's up to you whether to write/respond after reading their profiles.  If they sound appealing, it can't hurt to respond.  On the one hand, maybe they are just lazy by doing that, and on the other, maybe they're clueless as to how this thing works, too.  The good ones will send (or respond with) an email showing that they at least read some part of your profile.  Or, you could always prompt them with something like, "Thanks so much for writing!  I'm curious to know what piqued your interest in my profile."  Then, they'll either answer that question or they won't.

Question: A problem I am currently having with guys is the "date follow-through."  Guys will ask me out on a date online, usually saying something like "Let's get drinks next week."  I say something like, "That sounds great. I'm free on Tuesday and Thursday after work around 6:30."  Then sometimes, they don't get back to me. Or (in the case of the one guy I had a great date with) he said, "Let's hang out this week."  I gave him my schedule in the same way as above.  Then he tells me that he's busy this week.  I say, "Maybe the weekend."  Two days later and no response. 

I think that I might be too forward with guys.  I'm a very forward and direct person in general and have to make sure that I limit this trait because guys want to be in control.  When guys casually ask me out on a date online, is there a better way to make it happen without scaring them off by being too forward? 

~ Chelsea, 23, Philadelphia, PA

Answer: You actually remind me of myself in terms of being a planner, and there is nothing wrong with that—it's just your personality.  Doesn't it annoy you when a guy doesn't follow through or drops the ball?  Well, if it annoys you now after one date or even before the date, it'll annoy you throughout life.  So, rather than changing your tactic (giving two choices, like Tuesday or Thursday, as you said, is what I would recommend as well because it tells him when you're free but ultimately lets him pick the final date), it's more about finding a mature guy who actually takes the lead and doesn't just casually ask you out with no intention of putting something on the calendar.  If you do want to soften it a little, you could say, "That sounds great.  Tuesday or Thursday might work for me if that works for you."  It's a little less forward and more "cool" with the word "might" in there and removing the time (after 6:30).  But, to be honest, the way you responded was more than appropriate.

Question: It's been my experience that women sometimes read into things that men simply don't.  For example, if a guy sends an intro email at 2:30 AM, it may be perceived in a negative context… something along the lines of "what is this idiot doing up at 2:30AM on a Tuesday?"  Is there a good, or should I say politically correct, time to be sending these things? 

~ Matt. 37, Washington, D.C.

Answer: It's true—people (although, it's both men and women) read into things that we shouldn't sometimes.  I'd try to email back at night (maybe before midnight) to make things look a little more "normal."  But if that stops a woman from responding, that's just silly.

Any other burning questions?  Feel free to leave them in the comments.  Or, read more in Love at First Site, available online.