I’m connecting with people on dating apps, but rounds of flirting and conversation aren’t going anywhere

Dear Wayne and Wanda,

I need some dating advice. I feel like I am on all the dating apps, and it generally isn’t hard for me to match and connect with people. At any given time, it feels like there are at least a few people I’m chatting with. I have no problem striking up a conversation with someone and I think I’m a really good flirt too, at least on paper. It’s pretty common that within a few rounds of talking, a guy is flirting right back, and I sense there could be some chemistry, which is always exciting.

Where I’m having trouble is taking it to the next level. I can’t tell you how many times I’ve invested days or weeks in a guy, but any attempt to meet in real life is met by his excuses, or putting me off. I am not the prettiest, or thinnest, or most successful woman out there — but I think I’m a catch, frankly, and I really don’t think this is a matter of some physical or emotional shortcoming.

It’s like I’m in this spin cycle of collecting flirtatious pen pals but I can’t actually get any guy to want to come meet me. What am I doing wrong? I would appreciate straight talk — as much as I run this scenario by my girlfriends, I get a lot of, “This isn’t you, it’s that the guys out there suck,” and I can’t believe that’s all there is to it.

Wanda says:

A problem with online dating is you’re essentially in this arena that’s drawn all kinds of players, and you have no idea who you’ve squared up against. Consider this: At any given time, you may be talking to someone who wants to get married and birth babies already; or you’re facing off against a person who’s tentative and unsure whether they’re ready for the real deal, but they’re kind of trying; down the chain farther yet are the hook-up seekers; and even beyond that, you’ll find the bored and insecure — or already coupled up — who just want the affirmation of interaction with someone interesting and reciprocal.

You haven’t indicated what precisely you’re looking for, but you’re at the very least gunning for a romantic interlude, if not something more substantial, and instead you’re repeatedly hitting brick walls by encountering people who can’t even rise to the occasion of meeting you in person. That’s frustrating for sure. Why is it happening? There are any number of answers.


For one, you could be landing in that pool of people who really aren’t there for dating or hook-ups but are at best lonely, or at worst, catfishing their way through a series of hopeful singles as a means of self-entertainment. Also on the worst-case scenario side, you might be interacting with people who are frankly unavailable — as in, they are already married or committed or are just curious about the feelings around flirtation.

I applaud you for continuing to try. I would encourage you to not give up. And I would suggest moving forward, be as completely honest as early as possible about what it is you need to weed out people who are wasting your time.

Wayne says:

So, you know what you’re good at — small talk, flirting, baiting the hook — but you aren’t landing the fish. How about trying something else, then?

I mean, continue being yourself. That in itself is a rarity in the online dating world and should really position you to do well. And again, it’s — mostly — working. But if you’re serious, it’s time to start approaching this with more seriousness, assertiveness and straightforwardness instead of dancing around typing sweet nothings that get you nowhere beyond the DMs.

You want to close the deal? Be a closer. Don’t chat with these dudes for months. Don’t waste your time with never-ending correspondence like you’re living a world away from one another. If things are buzzing after a second or third round of communications, throw out a, “Hey, you’re cool — let’s meet for coffee” or “Hey, you’re fun to talk to — let’s do it in person and go for a walk at Westchester Lagoon.” This will quickly weed out the folks who aren’t serious or aren’t real. This also won’t give them time to fish around to see what else is out there, or get distracted, or start thinking you aren’t serious because all you seem to want to do is exchange messages.

Good luck!

[Is dating really so bad in Alaska? These Anchorage dating coaches say no — but you have to be open-minded.]

[Anchorage’s dating pool is so small, and the pandemic isn’t helping. How can I meet new people?]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at