How To Start A Conversation Once You Have Matched On A Dating Site


There is a tremendous amount of information and coverage around photos for online dating profiles these days. There is an endless source of tips, tricks and secrets circulating all over the internet today. As an online dating photographer, my goal is to not only make sure clients have great, natural photos but also have the supporting captions and profile to entice conversations beyond matching.

Should you look away or look at the camera? Should you smile with teeth or show no teeth? If you have managed to successfully navigate those waters and happen to match with a special someone — great! Congratulations!

You might think the hard part is done but many people (especially men) fail to turn matches into successful conversations let alone a date! There is a tremendous amount of pressure to play it cool yet be charming, witty and smooth but a large number of men end up going nowhere at this stage. Not to put any pressure on either gender but it is not uncommon for less than 25% of matches to end up with a first date.

So many things can go wrong here that I feel it is important to highlight some important tips to minimize the anxiety and low responses from matches.

1) Respond in a timely manner. Apps like Bumble or CoffeeMeetsBagel force you to respond with a set timeframe so that is taken care of but other apps like Match, OkCupid or Tinder have no time limit. My rule of thumb is to follow up in the same amount of time you would to a friend’s email or recruiter’s email. That can be a matter of hours (3–6 hours or 1–2 days). 
Obviously there are exceptions to the rule i.e. out on vacation or dealing with a personal matter but in those cases you can mention the reason for the delay. i.e. Hi, sorry for the delay, I was out at Yosemite or Napa with friends this weekend. Glad we matched! You have some interesting hobbies — where did you learn to develop a passion for XYZ? This does two things, one explain the reason for the delay, two illustrate you are social, have friends and are busy on weekends and three are thoughtful in focusing your time with said friends especially if you do not see them often.

2) Find a good talking point. As much as I don’t like people waiting to respond to messages, I do think it is important to think about what you write. Review the person’s profile, find something interesting, unique or quirky to comment on and be sure to spell check! It is important to be specific. If you write something like I noticed you like tacos, I like burritos, we should meet, that might not be effective unless you have some dry sense of humor that the other person gets but this can be tricky. However if you mention that you did a taco crawl recently and found some amazing place under the radar that challenges Nate Silver’s calculations, that might be more successful. The point is, being specific acknowledges the fact that you paid attention and put the time and effort to come up with an opening line.

3) Have good talking points in your profile. If you do not have any interesting details, insights, random observations or items in your profile, it will be difficult for someone to find something to reference in conversation. Details in photos and captions provide assistance in keeping the conversation going.

4) Use good grammar and avoid unnecessary emojis. This seems super obvious but this is sadly a fading quality in conversations these days. A little goes a long way in using full sentences and appropriate punctuation. I am not saying you have to ditch ‘Lol’ and ‘OMG’ but if your repertoire includes ‘TL;DR’, ‘UR’, ‘BCUZ’ you should rethink your approach. Also if you want to eat tacos, write it out. Do not use the taco emoji for goodness sake. I am no saying tacos will lead to a first date but using emojis in conversation will hinder your chances of ongoing conversation and dates (more so for men than women).


For help with dating app questions (i.e. how to select photos, which apps to use, when/how to messages matches etc.) check out myFrequently Asked Questions page or contact me directly.