How Can I Be More Confident With Women On Dating Apps?

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How Can I Be More Confident With Women On Dating Apps?

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Estimated reading time: 15 minutes

Dear Dr. NerdLove: 

So I’m a very outgoing guy. I love meeting new people and telling stories- I’ve lived a pretty unconventional life throughout my twenties. Most people I know would say I’m a gregarious but comfortable person. I love when I’m out somewhere and I learn new facts and make new friends.

But when it comes to online dating, I’m an absolute mess. I can’t ever figure out how to get the conversation started with another person. I’d much rather meet IRL, but I also totally understand the reservations women have about that and know it’s not really the way to go. And I also feel that asking someone out while in public or at the bar either presents as ethical malpractice or even just makes the other person uncomfortable. So I’m stuck in a constant state of being on Tinder, matching with someone, and awkwardly hemming and hawing until a meek “Hey” comes out, whereas when I’m out on Friday night, I feel totally confident about asking strangers about what bird they would be based on their personality.

It sure would be cool, rad even, if I could figure this out because I’d like to have a little more intimacy with someone.

Thanks in advance Doc!

Just Say The Words

OK, I want to start with the part of letter that doesn’t have an obvious connection to what you’re asking about, but I suspect is tied to your issues with chatting someone up on Tinder.

You mention that you feel like asking someone out in person is an ethical minefield because… reasons. This sounds to me more like a fear of rejection that has been sublimated into a fear of consequences for that rejection. A lot of people who worry about approaching someone in person – whether at a bar or club or just in a public space – talk about worrying about making someone uncomfortable or otherwise coming off as a creep. But when you dig into the nitty gritty of it, what they’re worried about is less “creeping out one person” and more “…and then I become the Main Character on TikTok”, a la West End Caleb or others.

While I don’t doubt that the folks who worry about this are worried about making someone else uncomfortable, the bigger issue – from what I’ve seen over the years – is more of a belief that their interest in someone is so inherently and definitionally unwelcome that they feel that if they don’t present themselves perfectly and carry on the interaction with such skill and precision that James Bond would hit them up for lessons, they’re going to be shamed so hard that they’ll be blasted out of the universe entirely.

(Hang onto that “gotta handle this perfectly” part, it’ll be important in a second.)

Now, I can absolutely understand that fear, believe me. And I won’t pretend that the risk is zero – God knows there’re plenty of folks across the gender spectrum who seem like their entire thing is dating-for-outrage-content – this is one of those times when the fear is out of proportion to the actual likelihood of both a transgression that bad or the odds of someone deciding to put you on blast. The risk exists, yes… but so too does the risk of being struck by lightning, getting hit by a meteorite or being attacked by a shark.

While there’re arguably exceptions (see again: West End Caleb, a topic I have many thoughts about), the sorts of interactions that are held up as “men, don’t do this” are guys being boorish or ignoring the lack of interest in other people, not folks having an otherwise good conversation that culminates with asking them on a date or for their number.

If you’re confident enough and socially skilled enough that you can recognize when it is or isn’t appropriate to flirt with someone and/or your ask is “hey, I’d love to get a drink with you/ go to this museum exhibit/ go go-karting”, the odds that someone’s going to be offended, insulted or otherwise upset that you asked them on a date are vanishingly low. And if you can take a “no, thank you” with good grace and let it be, then I think you’re in fairly safe territory.

Now, this brings us back to your question.

It’s interesting that you have a harder time starting conversations on dating apps than in person, JSTW. One of the things that folks often find easier about dating apps is how much easier it is to talk to folks on there, as opposed when you’re standing in front of them. People often find it far less intimidating to text a relative stranger, especially since that gives them more time to think and respond.

Of course, this only works if, y’know, you actually start the conversation. But that’s literally all you’re trying to do. Whether you matched on Tinder or you’re standing next to them at the bar – or at Barnes and Noble – then all you’re doing is getting the conversation started, something you’re already accustomed to doing in person.

And here’s the thing about the dating apps: the bar hasn’t been lowered for you, the bar has sunk through the floor and the Mole People at the center of the earth are wondering where the hell this thing came from. The first message men send to women on dating apps tends to be twelve characters long on average. Not words; characters, including spaces and punctuation. Part of why women get frustrated on dating apps is that the majority of messages they get from their matches is “hey”, “’sup” and “WYD”. It’s really goddamn hard to get a conversation going from that cold of a start. Giving your match something to respond to and actually engage with isn’t just going to make you stand out from the crowd, it also makes it easier to talk to you, because you’re not starting with trying to make her do all the heavy lifting.

Not to mention, if someone’s done a decent job on their profile, there’s a lot to use as a starting point in your conversation with them. Do they list favorite foods? Favorite books? There you go, conversation starters. Do they talk about pets, vacations? Do they have open loops or hooks in their profile that invite questions? Well, the whole reason they’re there is for you to ASK QUESTIONS ABOUT IT. If I talk about the time I was nearly trampled to death by elephants on my Hinge profile, it’s not because I don’t want people to bring it up.

What if they don’t have much in their profile to work from? Well, if their profile’s mostly blank or not terribly well-written, my advice is to just move on. But if you’re determined to try to make something happen, there’s always their pictures. There’s almost always something in their pics that you can comment on or ask about ­– things that aren’t about their looks or how hot they are. You can ask about what the story was behind that picture, what inspired that particular moment… almost anything really.

But here’s the thing: you don’t need to be perfect or witty or the smoothest, any more than you meet someone in person. Despite how it feels, you’re in competition with anyone else, and you’re not trying to out-clever, out-quip or out-flirt everyone else talking to her. You don’t need to be perfect or the best, you just need to be engaging and fun to talk to. That’s really it. Keep in mind: women on dating apps have just as hard a time trying to engage with people THEY like and get just as anxious about it. So the easier you make it for them to engage with you, the more fun it’ll be for them.

And the easiest way to engage and get the conversation going would be to ask questions. Questions invite responses, especially questions involving things that they chose or clearly care about. So asking about things that they’re clearly interested in – especially when you’re interested as well – will increase the likelihood that they’re going to want to talk to YOU instead of Captain Monosyllable and the crew of the SS Send Nudes. Just try to be mindful of not sounding like you’re about to use that question as an opening to go Alpha Nerd on a topic. Get their thoughts and opinions, show interest and let them lead the discussion on it; most guys tend to dominate and end up talking over them. If you’re the person who clearly wants to hear what they have to say and appreciates their insight, you’ll be a much more engaging person.

Oh, and a useful trick? Ask for a suggestion or recommendation. “Hey, you like $AUTHOR? I’ve really been interested in checking them out, what book would you suggest is the best to start with?” or even “Is there a book/TV show/movie that you think EVERYONE should need to see?” not only invokes the Ben Franklin Effect – we do things for people we like, so if we do a favor someone it must mean we like them – but positions the conversation as your acknowledging their authority/taste, rather than trying to show off YOUR nerd plumage to win her over.

Good luck.


Dear Dr. NerdLove: so, long story short, this girl coworker I liked got fired, I believe, and I found her through Facebook and started talking to her through Messenger, and first all I said was “Hi, %NAME”, she responded a couple of minutes later with “Hi”. Much later on my shift, I responded back with “yeah sorry for being late with this, just wanted to see if you’re okay”, and she responded with only a heart next morning. So, later that day I wanted to see if I can delve deeper into a meaningful conversation and I said “so what do you like to do for fun?” To then I added “Because I hate the thought of not seeing you at work anymore”… she never responded back. 

So Doc first I’m curious about what’s so wrong with what I said because I showed it to others and they told me it’s creepy. 

Next I really like this girl and I don’t want it to be over at this point, so is there any way to come back from that?

– Was It Something I Said

Ooof.

No, you weren’t an absolute creeper, WISIS, but you didn’t exactly cover yourself in glory, either.

Let me start off with the fact that no, I don’t think there’s any way to come back from that. Not because you screwed up so badly that nobody would ever want to interact with you – you didn’t – but because there’s no “back” to come to. There’s no “there”, there.

From what I’m gathering in your letter, you never had a connection with her in the first place, outside of being coworkers. So, right off the bat, you were trying to make something out of nothing. There was no foundation, no connection, nothing to build on in the first place.

And while that’s not necessarily impossible,  you made choices that ensured that you were never going to pull this off.

Let me break down just how and where it went wrong. First and foremost: you had to track down her Facebook profile. While that’s not inherently creepy, it is going to at least put someone on her guard. This is one of the reasons why I think it’s clear you didn’t have a connection already; presumably you would have already had SOME way of contacting her if you did. Plus, not being a friend on Facebook means that your chat requests go into a different folder, one she’s not likely to see immediately. So even under the best of circumstances, not being connected on social media already adds a layer of difficulty.

But hey, maybe you two had a lot of mutuals because of work or something. Like I said, not inherently creepy, but definitely going to make things harder for yourself.

The next issue is that you were messaging her on what was likely the low-point in her week. Even if this wasn’t her dream job or this paycheck was the only thing between her and living out of her car, getting fired sucks and most people feel like shit afterwards. So they’re not going to be terribly receptive to someone trying to flirt with them. Trying to do so is going to seem crass if you already have a connection. If you don’t, then it comes off as your being opportunistic at best.

If you add that to the “not mutuals on Facebook” factor, then you’re basically starting with a pretty serious handicap, even if you do everything perfectly.

Here’s the thing, though. You were actually doing ok at first. You were actually in a position to overcome the significant handicap you were dealing with. It may not have lead to the results you were hoping for, but you could at least made a friend when you weren’t friends before.

You were checking in because hey, she got fired, that sucks, you wanted to see if she were ok. That’s actually kind of sweet. Someone wanting to make sure you’re doing alright after a shitty experience is a nice feeling, even if you’re not close. It says that people noticed, people care, you’re not alone and ignored in this cold cruel world.

If you’d left it there, you would have been fine. That heart react meant that she appreciated your checking in on her. If you had followed that up with something like “I know we didn’t talk much at work, but is it OK if I send you a friend request?”,  you’d be in a decent position to at least start building an acquaintanceship. You might, with some skill and care, have been able to build that over time to a friendship or at least a see-each-other-in-person-occasionally that might have made a connection possible.

But you didn’t. And it was what you did next that ruined those chances.

You pivoted from “I’m expressing concern and compassion” to “and now we’ve reached the ‘hitting on you’ portion of the evening”, which is exactly what she didn’t need right then.

“…so what do you do for fun,” is the sort of thing you say to someone you just met on a dating app or were just introduced to, not something you say after expressing your condolences after a shitty experience. It signaled that your compassion over her being fired may be less than sincere, or at least secondary to your interest in getting in her pants.

Now, again: you could have left that there. You’d still be sans friend, sans coworker, and sans date, and it still would’ve been cringe as all hell. For all that, though, it wouldn’t have been as bad as it was about to get.

That’s because the very next thing that you said didn’t just kill your chances, it dug them back up, drove a stake through their chest, cut off the head, stuffed the mouth with communion wafers, then buried the head and body separately at a crossroads.

Sure, “…Because I hate the thought of not seeing you at work anymore” wasn’t the worst thing you could have said in that moment, but it sure as shit wasn’t much better. In those twelve words, you:

A) expressed an absolutely unearned level of familiarity to her, and

B) made her getting fired about your feelings.

Even under the best of circumstances, this signaled a lack of emotional intelligence and maturity on your part. Some people might find it uncomfortable, but even more would find it clueless and borderline insulting.

There’s a time and place for everything, and this was neither.

I understand what you were aiming for, here. You were trying to express that you found her presence to be a net positive in your life while at work and you’re going to miss that. You were, functionally, trying to pay her a compliment and express interest in her at the same time. The problem is, that’s not how pretty much anyone else would take it, especially under the context in which you said it.

It would be one thing if the two of you were friends. If you had the kind of relationship where you two were emotionally close, or even if it were the case that you regularly talked or hung out during the work day or otherwise kept each other entertained and engaged while on the clock… yeah, you could get away with expressing sadness that that she was no longer there. That isn’t about you, so much as acknowledging the loss of a mutually shared good time.

But since you didn’t actually have that relationship, your expressing this was presumptive at best, and it signaled that you considered that the worst part about her losing her job was how it made you feel.

And, more to the point, it hammers home that you were acting like an out-of-work teacher: you had no class. You saw her getting fired as an opportunity to hit on her. That’s not cool, my dude.

Even if you didn’t intend it that way, this progression – from condolences to ‘so… what’re you up to tonight?’ – comes across as if you saw this as your chance to get a date being more important than someone dealing with having lost their job. If a person were especially uncharitable, it could come across as if you were hoping that she were emotionally vulnerable and thus more likely to say yes, because you felt like she’d say ‘no’ under other circumstances.

Do I think you intended that? No. But what I think matters less than what she thinks. And it’s pretty clear what she thinks is “Go Away”. 

So what do you do from here? Well, to start with, you let this one go. There’s no saving this, and there’s no coming back from it with her. You burned this bridge pretty thoroughly, and you should probably feel lucky that other folks aren’t toasting marshmallows over the embers. Even if it’s not creepy – I don’t think a reasonable person would see this as potentially threatening or making them feel unsafe – it definitely sends a message that you’re less concerned with her than your own needs and interests. 

What you should do is take this as a learning opportunity. You should have stopped while you were ahead, when you had gotten to the point of her appreciating your expressing concern. If you’d stopped there you might – and I stress might – have had an opportunity to see if you and she had enough in common to make a connection.

The lessons here are:

1. If you like someone, the time to start trying to build a relationship with them is before they get fired. If you’d been friends at work, this wouldn’t have been as big of a screw up.

2. If you’re going to message someone you don’t have a connection with out of the blue, keep it short, respectful and relevant. A simple “hope you’re doing ok” would have been acceptable and was clearly appreciated.

3. Someone else’s bad day is not the time to hit on them. Especially if you only know each other well enough to nod at.

4. Don’t assume levels of intimacy you don’t already have. Like using an insulting nickname for a stranger on social media, you didn’t earn that right, and its presumptive at best to do so.

5. Don’t prioritize your feels over a relative stranger’s horrible day. Nothing about your relationship with her made your feelings relevant to the situation, nor is the fact that you’re interested in her (or that you’re sad to not see her at work any more) more important than the fact that she just got goddamn fired and needs to figure out what she’s doing next. Your feelings will be ok; she’s in a much dicier state than you are.

Now you know better. Learn from this and resolve not to make these mistakes again.

Good luck.    

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