Negotiating the First DATE – Set the Tone for A Successful Relationship

OK, so you’ve been contacted by someone online who has asked you out on a date… What now?

There are a few things to keep in mind that will help you navigate the first steps of the in-person part of this process.  I’ve laid them out below

1) What Kind of Date to Accept/Decline

-Coffee Date

Although this is common in the online dating world, I find a coffee date to be unacceptable.  It screams  “I’m cheap” and shows a lack of willingness to invest both money and a full evening or afternoon in getting to know you.  They can at the very least buy you lunch!

-“Let’s meet for a drink”

This one can go either way.  As I mentioned in my earlier post, if this is a same-day/same-night invitation, the answer is a very clear NO.

If you are going to accept this invitation, make sure it’s at least three days out, and make sure the time for meeting is between 6 and 7:30.  Yes, this is often an instance of “let-me-see-if-I-like-you-before-I-commit-to-a-whole-evening-out”; however, if it’s between 6 and 7:30 in the evening, if you are getting along, it will transition into dinner: a legitimate and 100% respectable 1st date. This is what you want.

If the drink is for 8 or 8:30, it could do either way; if the drink date is set for 9 or later, it is an indication that the expectation is either that you will have one drink and say “good night,” or  if you get along, the evening will turn into “drinks” which, having completely bypassed the formal indication of a “real” date (dinner), could be an easy segue into a night of intimacy, and likely a one-night-stand or a booty call at best.


Yes.  Scheduling a dinner means that a man is serious enough about finding a real relationship that he is willing to spend his time and money making sure that your initial contact fits the bill for an official date.  If you both choose to move forward in a relationship, it’s started off on the right foot.

This being said, there are a few parameters for what makes a dinner venue appropriate – or inappropriate.

Inappropriate vs. Appropiate Venues:

If you are a fan of “Sex and the City,” you may remember the initial date between Carrie and Big.  OK, so they slept together on the first date which is not usually a good idea but has not always ended in disaster.  After sex, however, he took her to dinner at a Scezhuan restaurant, where she ran into a friend who was on a date with a woman whom he later admitted he was embarrassed to date publicly.  She realized that Big was taking her to dinner at a place where he could take her out, while at the same time remaining anonymous.

This is a real thing.

You know the places.  I have many male friends who use online dating to hook up with women they would never date seriously.  Sometimes they take these women out to dinner first.  If the woman is one they would not date seriously, they choose the restaurant accordingly.  These venues typically are 1) close enough to their house (or your house) to make heading back to their place or yours “for a night cap” a reasonable and easy choice, and 2) somewhat under the radar (think: a place they would be very unlikely to run into anyone they know).

Make sure your date chooses a venue which is reasonably populated with people and not too dark or off the beaten path.  If your date is not comfortable taking you to a place where they might see someone they know, they may not have designs on a long-term partnership with you.  They may even already be in another relationship.


Although I am partial to dinner, lunch is a perfectly appropriate choice.  It’s a reasonable time and money commitment, and it certainly doesn’t indicate that they are trying to get you into bed and move on to the next.  Also, some people are not big drinkers, so lunch is a nice way to get the “official” nature of a first date in while not letting booze get into the picture.

2) Always Let Him Choose the Venue

The first reason for this is tied in to an assumption which I HOPE is true: YOU WILL NOT BE GOING “DUTCH.”  Please.  If a man is unwilling to pay for a first date, he is not worth dating at all.

Since he is paying, it would be presumptuous and inconsiderate of you to decide how much he is going to spend.  And if you have chosen the restaurant, it may indicate that you are at least willing to consider taking responsibility for the bill.  Nope.  You are not.

…But what if he asks you where you would like to go?  A very common question, and a good one!  If he asks you where you would prefer to go, offer a few suggestions, and be sure there are a few different options for how much the date will cost.  It is ideal to suggest two or three places with varying prices on the menu.  That way, if cost is a concern for your date, he can go online and review the menus to know what he can expect to pay.

And when you suggest options, don’t be obvious that you are giving him price options.  say something like, “Place A has a great outdoor patio, but Place B has great oysters – either would be great.”  You want to be conscious of the issue of money, but you don’t want to make a huge deal.  It’s a touchy subject.

Not all great men are flush with cash; but all men who are not flush with cash… don’t feel great about it.

You don’t want to put him in a position which might make him feel uncomfortable or overextended.  Remember: you want to really get to know him to see if he is a good match for you.  If he’s put in a place where he’s feeling defensive or resentful, you’re going to experience his quirks and not a nice, clean version of him.  We all have our quirks, but we don’t need to see them right away. We can get into all that later, once we’ve seen if we can enjoy one another’s company.

Another great thing about having him choose the venue is that it can reveal some pretty great information about him!  What is his taste like?  Is it compatible with yours?  Is he looking for a woman who dresses up, or one who wears jeans on a Friday night?  Does this fit with the kind of person you are?

This is all great, very useful information.  You don’t want to pass up the opportunity to learn!

Once your date is set, you can get ready for the first date!

I’ll check back in with tips on navigating that first date.

Don’t worry, it will be fun!





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