So, you’ve taken the leap to creating a profile and are ready to meet someone new. As a veteran and interminable optimist of the online dating world, I have a bit of wisdom that may help with your search. A little about me: I divorced when I was 34, married for 12 years, and now I am 51. I have been in a few long-term serious relationships and several brief dalliances – many of which comprise a lot of the content in my memoir, Broken Whole.

There are two primary aspects to look at when deciding whether or not to make contact with someone: their photos and what they have written about themselves. Photos grab your attention and either tickle or deflate your curiosity about clicking any further into the profile. As the saying goes, a picture is worth a thousand words. Take note of where the photo is taken and who is in the photo with him.

Location Location Location

Where the photo is taken can tell you a lot about the man. Outdoor-in-nature photos show that he values being outside. If you see him on ski slopes, white-water rafting, hiking, and fishing, you know he is an avid outdoorsman and he expects his companion to share some if not all of those interests. Match these photos against what he’s written in his profile. If he offers that being active is at the top of his list, then this will likely be how you will be spending time together. If you are equally as invested in spending time outdoors, a match made in heaven may lie in wait. Beware of his need to have to do this versus love to do this. If he has to be outdoors as a means to be happy, you might be in the presence of an addictive personality. If there is just one photo of him outside hiking, then you can assume this is something he likes to do, but it is a casual activity that he enjoys every once in a while.

Is he at a sporting event with his arm around a buddy, holding a bottle of beer? It is safe to assume he likes sports, his friends, and is a social drinker. But you may be off the hook if sports are not your thing, because he has friends. If most of his photos are of him at a sporting event, then this is all he likes to do.

Are all of his photos at a bar or at a party? Chances are this is at the top of his list for having fun. If it’s yours too, may the search be over and bliss be yours.

Is his profile photo a selfie taken in his living room? What does he have hanging on his walls? Are there books on shelves or end tables? What does the furniture look like? Does it look clean or cluttered? Is he at the kitchen table with the living room behind him, or on the couch, or standing up by the front door? While this particular photo could be staged at a friend’s house, it can still tell you something about him. If there is nothing on the walls, or only something practical like a coat rack or key holder, then you can assume he does not have much affinity for aesthetics or art. And it may follow, unless you can spot books somewhere in the background, that he does not read. Is the furniture current, a holdover from his fraternity house, or family heirlooms from grandparents? If the furniture is current, he values modern styles. If it’s from yesteryear, he may be frugal, have a hard time of letting go of the past or both. Is there clothing thrown around or on it? If so, he’s telling you he doesn’t care about what others think, he’s not much for convention, and he’s messy.

The living room photo is still a far cry better than the selfie taken from inside the bathroom. While there is the useful technology of the mirror from which the photo can be reflected without the angle and depth issues that frustrate the most adept selfie-photographers, the bathroom-mirror selfie conveys a couple of things. First, he doesn’t want anyone to know he’s taking a photo of himself. So, he may be hiding from a girlfriend, wife, roommates, or friends. The second thing it conveys is that he has no friends who could take the photo for him. A third possibility is that he is not thinking about either one of the above and just wants to get a photo taken quickly and a mirror makes it easy. Trading in haste for thoughtfulness may be telling you something else altogether, however: he’s afraid of being alone and getting attention from women online is better than another moment of staring at himself in the mirror. And if he’s feeling that afraid of being alone, clingy and a constant need for your approval may be not too far behind.

Who’s in That Photo?

He’s nicely dressed in a suit or tuxedo, smiling, happy. But wait, his arm is around someone else, a face you can’t make out because he’s cropped it. Who was this person? A wife or girlfriend, a sister, mother, or cousin? A mixed message is the best this conveys. It announces how good he can look when he’s dressed up but it also harkens back to a happy past moment that begs questions of who was on the other side of the photo, what happened, is he over her, does it matter, and why was he too lazy to have a photo taken of himself dressed up without the ambiguity of cutting someone else out?

And then there may be the series of photos where he is seen with multiple women, which raises a completely different set of questions. Are you to believe he’s a lady’s man, a good friend to women, or just that he was chosen as the token male for a photo at the last family reunion?

He loves his kids. His arm is around them in three out of five photos. He wants to be seen as a good father, he values his children, what could be misconstrued? He may be trying to prove himself and to the world that he’s a great dad, or that all he really has time for is his children, or that he wishes he had more time with them but because of a divorce decree, he doesn’t, or that simply, he comes as a package deal, and perhaps is looking for an additional or better mother for his kids. Looking at what he writes about his kids, if he does, may help answer some of these questions. Other answers will likely come if there is a meeting.

He Writes What He Means

While the photos tell a handful of stories about your prospective suitor, what he writes should fill in more. Whether he’s written a few words or has gone on and on for paragraphs tells you more than what the words convey.

The man who has posted one, maybe two photos, and a simple fragment about “just checking things out” is literal. He is not serious about finding someone. He is on the site to see what kind of women are there and if he’s interested in any of them. He is likely on multiple sites, the free ones especially, and is hoping that less will be more. He will stumble into someone who is not picky and who will not ask for much, he hopes. There are reasons why he has written so little about himself. He’s unsure about what he’s really doing there. He may be very recently out of a relationship (hours or days) and is desperate to find company. If he’s able to find someone to hang out with, all the better. He may be in a relationship but it’s not working out, or she’s wanting things to go in a direction he’s not ready for, so he’s looking for someone else casually in hopes of having a landing spot if and when he breaks up with the current girlfriend. If you’re not looking for a commitment either, this could be an ideal situation, but drama will surely follow if you or he shift expectations.

If he’s answered half or fewer of the prescribed questions for the profile, he is not picky and is in a hurry to meet someone, which likely means that he is more desperate than truly interested in finding a good match. He may also believe what he has written is sufficient, that nothing more is needed because he’s a stronger talker than he is a writer and wants to save something for the first meeting.

If he’s filled in something on all of the prescribed questions for the profile and the answers are substantive and thoughtful, he is serious and choosy. He may be open minded to a certain degree, but more than likely he has a clear picture of what he wants and is not going to settle for anything less. Perfect has many interpretations, but anyone looking for the embodiment of an ideal companion and believes he has found it will be less flexible and probably controlling when lo and behold there is a fumble and fall off perfection.

If he admits to being in an open relationship, do not harbor any secret intention of being able to turn him around and make him monogamous, if what you are looking for is an exclusive relationship. This is not a challenge that can be conquered. The fairy tale story of being chosen and triumphant very rarely applies in this situation. If you are also in an open relationship, then this may work for you. But if you are in an open relationship looking to settle down and commit to one person, being able to identify with someone else who has the same track record as you do may be appealing at first, but if he is not ready to shift gears, be aware and steel your heart against investing until you are sure. Easier said than done.


Photos, written description, and phone calls notwithstanding, there is no full-proof way of figuring out who the man is until you spend time with him, and even then, some people are masters of deception. If you’ve made it through a couple of meetings for coffee and dinner, and you’re feeling the mutual electricity of someone new, although it may be difficult to find moments when you can reflect a little and ask yourself questions, the beginning of getting to know someone is exactly the time to do this – before things dive in headlong into a point of no return. Watch for whether or not he does what he says he was going to do. Is he making excuses for why things didn’t happen? Was there some kind of drama that prevented him from arriving at his intended goal? What was it and could it have been prevented or maneuvered differently? If there was drama, how did he respond to it? Did he come to the aid of whomever or whatever needed help? Or, did he help with the intention of still completing what he intended for himself, but ran out of time? Some things will show themselves only after they have come around repeatedly. Is the pattern the same with the same outcome? Ask yourself if follow-through matters to you. Ask yourself if the drama that prevents the follow-through has interfered with being able to spend time together. Or, does he expect you to join in and become part of the folly? Do you want to join in? Is it better to join in rather than wait for him to have time for you? Is this how you want to be spending time together?

Looking for a significant other and dating him is more art than science. The rhythm of your new prospect’s ways of being will likely glide and chafe unevenly and determining how and if these matter takes time. It is hard to keep your rational mind intact when you believe you have met someone special. Being as clear as you can be about your own intentions may be your best gauge for whether or not you are suited to any new prospect. May you find your match and dance happily into the sunset.