Mr. Match’s First Date Plan


After a hiatus that included a committed relationship and a dating break, I’m back. I know I was barely here for long to begin with, but as I am back on, here I am. To coincide with a couple of first dates I am giving you a little insight into my typical first date plan.

I usually am the one to start the “okay, we’ve emailed long enough, do you want to meet?” portion of email interaction. Only a half a handful of the women with whom I’ve communicated have done it themselves, and that’s perfectly fine with me. As a result of moving things forward, I am also usually the one who either picks the place, or picks two or three venues at most and lets the lady decide. I actually like this because it makes it easy to execute the first part:

1) Pick a place that’s convenient to you both and will be conducive to conversation.
It should be easy to remember, but if I had a dollar for each time over the past two years that I’ve had to remind someone that they’ll want to be able to talk on their first date, I’d have been able to pay for lunch today and tomorrow. Going to dinner or going to the movies in my mind are bad first date ideas. I prefer to get to know someone on a first date, especially if we haven’t met before, and dinner or a movie don’t really give you the chance to do that. The first date spot doesn’t always have to be a bar (though it usually is), and doesn’t have to be whisper quiet, as that also can be unnerving. I like places where you’re likely to get a spot to sit down, or places that give you something to do (Trusty’s over by the Potomac Avenue Metro is great during the week because I’ve never been unable to get a table, and playing board games against my date tends to help the night along, and not make would-be awkward silences so awkward.) Do your research. Ask friends and consult websites like Yelp.

Okay, so you meet and things don’t go as well as you might’ve hoped. You say goodnight and go your separate ways. End of story. But say things do go well. You’re laughing and having a great time. You don’t want to keep drinking because nobody wants to get drunk on a first date, and you’re trying to figure out what to do next because you don’t want the date to end. That’s why you’ve already thought of…

2) Have a second venue in mind that’s nearby but different from the first, and don’t introduce it until you’ve ascertained that things are going well.
Whether it’s a stop at Julia’s Empanadas for an after drink snack, popping into a bar to play some skeeball, or s’mores at Cosi, I’ve always had a second venue up my sleeve that is always no more than a few blocks away. The suggestion to move somewhere else does many things, but one of the most important for me is that it tends to give me an idea whether she’s enjoying things as much as I am. That isn’t to say that if she turns down the invitation that she isn’t enjoying herself, but the odds are that she’s having a good time if she wants to go along.

Now you’ve been out for a few hours. You had a few drinks and maybe got a casual bite to eat, but now the date’s coming to an end. You had a good time, and you feel like she did too, so now you…

3) Set up date number 2.
I make a habit of walking her to where she’s going, within reason. If she’s getting a cab, I’ll make sure she gets in one. If she’s getting on the metro and it’s in the same direction I’m going, I’ll walk her there. If she’s taking the bus and it’s coming soon, I’ll wait. On the way, I open the door to the second date. “Would you like to go to dinner sometime next week?” is an easy one, but be flexible. If she talked about a movie she wants to see, or a museum she wants to visit, suggest that you go do that. Always suggest a specific thing, and always suggest a rough time frame. Asking her to “hang out” is not specific enough.

Now she’s said she’d like to see you again, and you see that a cab is pulling up for her. You’ve got to…

4) Decide whether to go for the kiss.
If it hasn’t happened already (say, on the walk to the second venue), this is a crucial moment. By now you should know whether you want to kiss her, but does she want to kiss you? At the time of the goodbye, I turn so that we’re facing eachother and with not much space between us (no personal bubble violation though) and say something like “I had a great time. I’ll call you about [date 2].” She says something in reply, and chances are she’ll either try to hug me, at which point I hug back, or if there’s a hesitation, I lean in for the kiss, because no girl I’ve ever known has gone for the kiss first. We hug or kiss, say goodnight, I open the door for her to get in the cab, close it once she’s inside, and she’s on her way. The end.

Of course not every date goes the way I think it will from phase to phase. Not every date that goes to two venues always gets to date 2 or 3. Not every first kiss leads to more. That said, having an actual plan to maximize the time you spend on the first date and find out if you want to see eachother again does significantly less harm than good.


Profile Pointers: Taking it to the limit


When writing certain portions of your profile, Match sets a max character limit. For the real meat of your profile, there is both a character max and a character minimum. This makes sense, as it’s the only non-negotiable in-your-own-words portion of the profile. Tell your potential match about you. It’s unfortunate that the minimum is so low (200 characters, if my recollection serves me well), because a number of people out there do just enough to reach it, and they often do so while lamenting the minimum. Oh my God, I have to write 200 characters about me? However will I do it?

If you’re a man seeking women, the onus is usually on you to initiate communication. In my Match life, I’ve received 3 winks, and 2 emails as the first communication from women (of those emails, one was from someone outside my dating demographic, asking me why I don’t prefer the type of women that she was, and the other was from someone in New York – that’s not exactly within my dating radius). You read the profile, send the email, and hope she responds. As much as I hate to admit it, I have a few different types of email that I send. They’re not cookie cutter, but the M.O. is the same within each type of email. No matter what the type of email is, it always indicates that I’ve read her profile without actually shouting it. In order for me to write that email, I actually need to have something to read in the profile. If your profile is 201 characters long and 1/4th of it is you complaining about meeting the character quota, what does that tell me? Next to nothing.

Ladies, if you’re not going to put forth the effort to effectively communicate information about you to your potential matches, you’re making it difficult for us to determine whether you’re someone we want to email because we’re not learning much about you. You’re spending money here (unless you aren’t, but that’s another post for another time), so shouldn’t you be getting the most for your dollar?

It’s not a group thing


“Heather” and I were preparing for our first date. There had been a few email exchanges, and we decided upon a venue. In the days leading up to it, we texted back and forth a little, and on the night of the date, she told me she was bringing friends. In my head I heard the loudest record scratch I could hear. Scrambling, I got a hold of one of my best friends to be my wingman, never having thought I’d need one for a date.

He met me at the bar about 15 minutes before they got there, and they’d been drinking wine. There were two of us and three of them, and we crammed into a tiny booth. As you might have predicted, the night was going about as well as Little Big Horn did for Custer and his men. She seemed to be more into talking to her girls, and my friend and I were just passengers on their night out. We decided to move to another bar. I’m not sure why I bothered.

At the other bar, I told my friend he could cut out because I was not far behind him. He left without much of a fight. About 10 minutes later, I told Heather I was following suit. She pouted and wanted to walk me to the door. Seeing no harm in it, I agreed. When we got outside, she wanted to make sure I was going to call her. I was stunned by that, since I had no interest in doing so, but I said I would.

I didn’t.

A first date is about getting to know the other person, about finding out who they are outside of the words and pictures on the screen. How well can you do that when you bring two tipsy friends along for the ride, and alert the other person to this hours before you’re slated to meet? Sorry, but I’ve got no interest in that.

Profile Pointers: No thanks, I’m just looking


One of the most confusing things I’ve seen on a Match profile is the phrase “just looking.” Most often found in the profile headline, it’s meant to… Actually, I don’t have the slightest idea what it’s meant to do.

When I see “just looking,” my initial thought is to look at the next profile. “Just looking” says “I’m just looking at profiles, not writing emails” and pretty much guarantees that I won’t take the time to read the rest of what’s written. Why would I? You’re all but screaming that you’re not serious about online dating, and since the onus is 99.9999% on the man to initiate communication in email form, why should we bother when you’re “just looking?”

Profile Pointers: Curves Ahead


“Profile Pointers” is a running series of tips that will hopefully make your profile better. I really think that these should be already understood, but from what I’ve seen that is not the case.

In the land of Match, fitting yourself into a category can be difficult. Is your hair dark blonde or light brown? You’re 5’4½, so do you list yourself as 5’4 or 5’5? Is “other types of exercise” sexual innuendo? It appears the most difficult is figuring out how to describe your body. What I find to be the most confusing descriptor is “curvy.”

I know everyone wants to make themselves sound like a great catch, the perfect mate for some lucky guy or gal. What should not be lost is that you need to be as truthful as you can in how you describe yourselves, and I’m pretty sure that you all know that. What you may not know is what the true definition of the word curvy is. Let’s break it down.

The word curvy is, breaking the laws of definition as pertains to using a form of the word to define the word, indicative of someone having curves. If you’re curvy, you have defined hips, probably a prevalent ass, and probably a handful or more in the breast department. Sure, it’ll vary a little from person to person, but that right there is a pretty good idea of what curvy means.

I’ve known a few large men who have made light of their physical condition by saying something like “I’m in shape. Round is a shape.” Apply that to the word curvy. If your body resembles one singular curve, that does not make you curvy. I really enjoy curves on a woman, but it is really frustrating to click on a profile that is supposedly of a curvy girl to find that it is not the case. Much of online dating is about truth in advertising; if you say you’re one thing, I expect to find that to be true.

There’s no reason to shoehorn yourself into a descriptor that is not truthful. If you have “a few extra pounds,” or whatever the true description of self is, say so. The truth is attractive, and it won’t make me skip over you.

Profile Pointers: Group Gaffe


“Profile Pointers” is a running series of tips that will hopefully make your profile better. I really think that these should be already understood, but from what I’ve seen that is not the case.

I hate to harp on pictures, but I find that most of the mistakes are made in this department. In this instance, I ask you to stop including so many photos of two or more people in your profiles. There’s nothing wrong with the occasional group photo in a profile. It shows that you have other friends, and that’s great to know. But you have to remember that if we have no idea what you look like, a bunch of group photos aren’t going to help us. Not only that, but then you’ve probably given us a whole bunch of other women to look at. Don’t you want us to focus on you?

Back Burner #1


I had been emailing “Lisa” back and forth for about a week. She lived close by, and we liked the same football team.  I pitched the idea of us meeting for the first time at one of my favorite bars and she accepted my invitation. The next day there was an email from her backing out of our meeting:

Mr. Match,

A friend of mine is coming to visit this weekend and he’s staying with me. We used to date and haven’t seen eachother in a while, so we’re going to hang out this weekend and give it a shot and see where it goes. I’m sorry to have to cancel on you, but if he and I don’t work out can you and I go out then?


I kid you not.

Now it shouldn’t take a brain surgeon to know that I did not write her back. To be honest I was flabbergasted that she would a) tell me that she was canceling on me for another guy, and b) have the nerve to ask me, in the same email, whether I’d essentially willingly be her second option. Sorry, that’s not going to happen.

Profile Pointers: Unfortunate Sun


This is the first of what will be a running series of tips that will hopefully make your profile better. I really think that these should be already understood, but from what I’ve seen that is not the case. ladies, this is a plea: Stop including pictures of you wearing huge sunglasses in your profile, especially if it’s your only picture. I’m sure you look great under those sunglasses, and I’m sure the sun was extremely bright on that particular day, but when 1/3 of your face is obscured, it can be hard to get a grip on what you look like.

Maybe I’m a guy who is attracted to a certain eye color. Maybe I like to be able to figure out how it will be to look into your eyes. Hell, maybe I just want to make sure that you’re not cross-eyed or that you don’t have a lazy eye. How can I do any of that when you’re wearing something that covers much of your face?

It’s somewhat acceptable to have a picture that shows you in those sunglasses as long as it’s not the primary photo, but what’s the point? The idea behind profile photos is to give the people looking an idea of what you look like from the shoulders up, from the feet up, and it gives us an idea of how you dress. On that list of things we’re looking for, there is no “I wonder how she looks in sunglasses.”

So please, stop making those photos your primary profile pictures, and maybe you should consider deleting them all together. Maybe you’ll get more looks with our eyes if we can get a look at yours.



My name is Mr. Match. I’m a 20-something living in Washington, DC, supposedly home of many, many singles. A fit of inspiration took me to in an effort to expand my dating horizons, but what I’ve seen so far has been a lot of maddening and frustrating wrongs, errors made by the women on match in their profiles, in communication, and in actual dates. As I go along, so too will this blog. Of course, I realize that I am not beyond reproach in my own dating practices, but that’s not what this is about, is it?

What you’ll hopefully see here are things that make you chuckle, and hopefully sometimes enlighten you as to what should and shouldn’t be done in the dating world, especially if you’re dating online.