Photo : verkeorg

Some people have problems that require delicate advice from a qualified professional. Others just need a random a guy on the internet to kick ‘em in the teeth (with honesty, that is). I’m the latter. Welcome back to Tough Love.




This week we I’m responding to a few advice seekers and tackling a question I get regularly: “How do I get people to respond to my online dating messages?”

Note: I’m not a therapist or health professional of any kind. People ask for my advice and I give it to them. End of transaction. If you have a problem with it, feel free to file a formal complaint here. Now that that’s out of the way, let’s get on with it.

I’m serious about finding someone, but when I connect with someone online, it seems they chat then stop. Or they say they live too far. Or just don’t respond at all.


Here’s another poor soul:

Hey, so I match with guys often but it never goes anywhere. I have tried waiting for them to speak first, saying a basic hello, giving compliments, and making a comment about something interesting I read in their profile. I’m very close to conceding and leaving dating behind... What should I do?

I’m going to let you all in on a very useful dating secret. When you reach out to someone on a dating app or website, do so with the intention of making plans right out the gate. Dating apps are meant to quickly connect you so you can move on to the actual dating part, not give you a space to endlessly discuss likes and dislikes until you’re certain you’ve met “the one.” Here are several reasons why opening with making plans is your best bet:

Just saying “hey” or “hello” is useless, especially if you’re using an app or service where you match with people through swiping or favoriting. The match itself is saying “hello,” so you don’t need to say it again doofus. Besides, it’s impersonal and does nothing to make the other person feel special. Jump right into the good stuff.

Chatting for too long makes the excitement fizzle and gives people too much time to rethink their matching with you. That’s when you get excuses about how they live too far away, or how work is keeping them so busy, or they just ghost you entirely. Good conversation is nice to have, but save it for when you’re in person.

Giving compliments is nice in theory, but they can also easily be taken the wrong way, or make you come off too strong. Intention is hard to read in text communication. If you’re going to compliment, compliment something they have control over, and use it as a means to make plans (see the example below).

Commenting about something interesting you read in there profile is better than just saying “hey,” but it still doesn’t move things forward. For example, a message like, “Hi! So you like board games? Me too!” isn’t ideal. You know they like board games because it said so in their profile. Are you asking them to confirm? And they know you know that they like board games because, again, it’s in their profile and you’re asking them about it. It’s good to establish similar interests, but there’s a better way to use common likes as a means to actually land a date (see the example below).

Even if you do chat for awhile and eventually make plans down the line, you have nothing to talk about when you finally meet up. What’s worse, you’ve taken these text communications and built up a fantasy version of this person in your mind. Chances are they’re much different in person and you’ll be disappointed. Don’t set yourself up for that!

Trying to make plans right off the bat also helps you weed out people—in two different ways. First, it forces you to narrow things down and really focus on people that you’re totally down to meet up with based on their profile and photos. Does reading about them excite you? Are you attracted them? Great, go for it. If not, move on. I know, I know, you’re thinking “But I want to chat with people to get a feel for them and make sure they’re not a serial killer” or whatever. Look, if someone seems sketchy enough that you won’t meet them at a public place, is chatting with them really going to convince you to change your mind? Also, if they are a serial killer, chatting with them only gives them the chance to manipulate you. Logically speaking, “getting to know someone” through text messages doesn’t make you any safer or necessarily help you get a better sense of who they really are. That can only happen in person. Second, opening up communication with an invite to meet up scares away all the people who aren’t actually down to date. All the online dating tourists that simply want a place to flirt, get attention, or browse won’t bother because they don’t want to actually meet people. Ask someone out—if they see your profile and like what they see, they’ll go for it. If not, you’ve saved yourself a ton of time and energy you would have wasted on trying to convince them to grab coffee.

Asking somebody out right off the bat is gutsy and shows them that you’re decisive and know what you want. A lot of people respond well to that kind of move, like “Oh wow, they’re not playing any games...”




Okay, so, what does a good online dating message look like? Say you find the intriguing profile of an attractive person that doesn’t seem sketchy. They mention that they like the hit HBO show Westworld, craft beers, and pizza—three things you happen to like as well. Here’s what you could say:

Hey! You seem pretty cool and I like your sense of style. Want to grab a drink this Saturday and talk about how awesome Westworld is? Tasty Za is a great pizza joint and bar stocked with local craft beer!


This type of message does a lot all at once: you get that awkward greeting out of the way if you need it (even if it is redundant); you let them know that you’re into their vibe; you compliment something they have control over; you immediately give them your intentions (you want to go on a date, duh); you bring up some of the things you both like; you give them a specific time and place to meet. All they have to do is look at your profile, check their calendar, and say ‘yes’ or ‘no.’ It won’t work all the time (which, again, is a good thing), but chances are they’ll give you a shot if they’re even remotely interested in you. Give it a try!

That’s it for this week, but I still have plenty of blunt, honest advice bottled up inside. Tell me, what’s troubling you? Maybe I can help. I probably won’t make you feel all warm and fuzzy inside, but sometimes what you need is some tough love. Ask away in the comments below, or email me at the address you see at the bottom of the page (please include “ADVICE” in the subject line). Or tweet at me with #ToughLove! Also, DO NOT EMAIL ME IF YOU DON’T WANT YOUR REQUEST FEATURED and PLEASE KEEP IT SHORT. I do not have time to respond to everyone just for funsies. ‘Til next time, figure things out for yourself.