Your Frequently Asked Dating Questions, Answered

I love my readers and I love giving dating and relationship advice, I really do. But I’ll let you in on a little secret. Your dating questions aren’t as unique as you might think. I’m not saying this to make you feel bad or basic, I’m saying this so you can find some comfort in the fact that you’re not alone.

The details might be unique to your situation but we’re all in the same boat, and I hope you find some comfort in that. We’re all in this together. We’ve all got the same burning dating questions, so let’s answer them:


How do I get over a dating slump?

Two ways: Push through and keep dating until you get out of the slump, or take a break, look at why you’re in a slump, then start dating again when you’re ready.

Sometimes you’re in a slump because of something you can address, sometimes it’s just a random string of bad events. If you’re not sure whether you should push through or take a break, consider why you’re in a slump. If the issue is external, like all of your recent dates just being mediocre, push through. If it’s internal, like  not feeling motivated to date after a break-up, take a break.


Should we be friends with benefits?

Sure!..As long as you AND YOUR PARTNER can answer these 5 questions with a “Yes”:

  1. Do you both want to be friends with benefits?
  2. Are you both able to consent to a friends with benefits arrangement?
  3. Are you both clear on what the friends with benefits arrangement will be?
  4. Are you both clear on what the friends with benefits arrangement will or will NOT lead to?
  5. Can you both say that you’re not settling for a FWB arrangement instead of what you actually want, like a committed relationship?

If you and your partner can answer Yes to all 5 questions, consider it. If you can’t, don’t consider it for a second.


Should we remain friends after we break up?

Maybe, maybe not. If it will stop you from moving on, No. If it wont, maybe. If it’s going to interfere with your love life, No. If it wont, maybe. Do you actually want to be friends in a completely platonic sense? If no, then No. If yes, then maybe.

Personally, I don’t think you should remain too friendly with an ex in most circumstances, no matter the seriousness (or lack thereof) of your relationship. Most circumstances, but not all.  So, maybe you should, maybe you shouldn’t. If you can have a healthy relationship with an ex, by all means go for it.  I just think most people can’t do it.


How do I respond to being turned down for a date?

  1. “Okay cool, thanks for the heads up”
  2. “No worries. Thanks for letting me know”
  3. “Ah okay. Well, best of luck to you”
  4. “C’est la vie” and then shrug and smile
  5. “Thanks for giving me a forthright answer. I wish you good fortune in your dates to come”

Any of those work (okay, maybe that last one is a bit dramatic, but whatever), and anything that is thematically similar would work too. What you should never do is respond with anything other than class and tact. Remember, a rejection is an opportunity to find someone better suited for you. A rejection is a kindness.


How do I respond to rejection over text?

See answer above


How to move from Tinder/Bumble/Matching and messaging on a dating app to text?

This doesn’t need to be restricted to a certain amount of time. You can switch to texting from messaging on whatever app you met on within the same day of messaging, or much later. Time isn’t the determining factor, but the substance of your messages is.

What substance should you have in your messages before switching to text? Simple, you need to establish that you have, on some level, a bit of chemistry. Can you hold a conversation with this person? Are you on the same page, or even in the same book, about what you’re both looking for? Not the details per se, but if you’re looking to go on a date, and they’re looking for a casual encounter, might be good to know before switching to text. This also might seem silly but, can you deal with their style of communication? Some people get really, really annoyed by the incorrect use of your/you’re, and if you’re one of those people and you give your phone number to someone who doesn’t grasp the difference, how annoyed will you be when they start trying to arrange a date over text with you.

Less specific, you should message long enough to get a read on someone. You wont always be right, but at the very least you should message someone long enough so that you get a good read on them as a person. What sort of date they would prefer, whether you see eye to eye on issues that matter to you, how they’ll behave on a date, things like that. If you manage to establish all these things within the first day of messaging, ask for their number. Do it when it feels right. Ask politely, suggest it as a transition (i.e. Would you want to transition to text?), and start planning a date via text.


How do you walk away from them and mean it?

Cut off all contact with them. Excise their presence from your life. Delete old emails, their contact information, get rid of any reminder of them. Go full on Eternal Sunshine of the Spotless Mind. Don’t bring them up, even if it’s just to trash them. Don’t think about them at all. Don’t reflect on the good times or the bad times. Walking away and moving on is an ongoing process, so just keep excluding them from every facet of your life. Physically, emotionally, mentally, and in your online life. Walk away and never look back.


They only text me every couple of days. Are they interested?

Think of attraction of any kind, or romantic interest of any kind less in a binary sense, and more of a sliding scale. At the extreme ends of that scale are attraction and disinterest,  with the center being ambivalence. Now, consider where you’d have to be on the scale to be interested enough with someone to maintain minimal contact via text, but not sustained interest. Probably close to the center, but leaning toward attraction. So yeah, they’re interested, but not that much. If you initiated a date they’d probably hang out if it was convenient, but they wouldn’t go out of their way to make things happen with you. They’re interest in you that way that people are interested in something if it’s free or easy.


Why do they keep liking my stuff on Instagram/Snapchat, etc, but they don’t talk to me?

I  believe that this behavior is what’s now being branded as “haunting” (btw, I hate all these new dating terms people keep coining. They’re all terrible. Please stop. Today, right now.). Anyway, don’t place too much stock in this behavior. It is remarkably easy to continue to follow someone on wherever they post new social media, because following someone is a passive act. It’s also easy to double-click on a photo, or open a video, like, or retweet something.

Why do people “haunt” their exes? They’re still interested in them,  or interested in their life. Doesn’t always mean it’s romantic. Maybe they’d want to get back with them, but aren’t very motivated to do so. Or, they could just have a lot of free time and a compulsion to check people’s social media output. But the reason doesn’t matter all that much. What matters is whether you’re interested in connecting with them again. If you are, reach out. If you aren’t, ignore it. If it bothers you that they’re “haunting” you, block them. What you shouldn’t do is dwell on this behavior.

Please stop dwelling on people who aren’t dwelling on you. It’s unhealthy.


If nothing else, I hope this post answers one of your dating questions…or you find some solace in the fact that people all around the world are asking the same questions that you are. If this post didn’t answer your questions, feel free to drop me a line via email.

Good Luck Out There.


Also published on Medium.

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