[Q&A – Dating]: Why would a guy flirt but never ask me out?

The Q:  From a woman, regarding men: “What is up with guys who flirt, but never make a move? He’ll flirt. I’ll flirt back. That’s it. What’s his hold-up?” -Emily*

The A: Few quirks in a guy frustrate a woman like his habit of flirting with her for no apparent reason (if you’re me, anyway, so I feel Emily’s pain). Frankly, flirting is fun, but it gets old when it’s with a guy who doesn’t attempt to pursue a relationship.

This is because flirting communicates something. When I flirt, I use body language and/or other words to say “I kinda have a thing for you.” It’s only natural, then, that when a guy flirts with me, I assume he’s saying “I kinda have a thing for you,” too.

But what if he isn’t? Maybe the hold up for some of the guys who flirt but don’t “make a move” is that they flirt because it’s fun, and not at all because it’s step one in their pursuit of a relationship. If a flirt flirts solely for fun, however, he (or she!) essentially says, “Here,” to the person with whom he or she flirts, “Have this expectation (the expectation, that is, that we’re probably on the verge of eating chicken piccata at a fancy restaurant while we pretend we haven’t Googled** each other).”

Then he or she never delivers.

But my guess is just a guess. Emily’s question would be answered better by people whose insight here is better than mine:


So here are a couple quick answers from a couple male friends and fellow bloggers:

Chris Schumerth: “Well, there isn’t ‘one answer’ to this, of course, but at least two possibilities come to mind, both of which too many men would undoubtedly deny. First of all, men are capable of being confused. It could be that he’s sort of interested but can’t decide if he’s really interested. The second thing that comes to mind, and this one’s probably the bigger of the two, is that mutual flirting doesn’t make facing rejection any easier! It’s hard to go out on a limb and ask a girl out!”

J.Q. TomanekMen are from Venus but we understand in Martian. When I flirt with my wife and she flirts back, I get the “flirt” but for some reason misfire on the follow-up. Guys can diagnose what kind of bird is flying during dove season, invented Morse code, and can translate a third base coach’s signal, but when it comes to reading women we need it LOUD, clear, and direct. At least for me, I take more risks with my wife when I have greater certainty that I know what she wants or expects.

A third guy whose feedback I sought shares more thoughts in an upcoming guest post. (Check back tomorrow!)

Edit 10/19/12: Click here to read the guest post in response to Emily’s question.

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Q&A is an occasional feature. If you have a Q, I can come up with an A (and if I don’t have an A, I’ll find somebody who does). To submit a question, email me at arleenwrites@gmail.com or leave it in the comments. No topic is taboo (although I can’t promise I will answer every question).

*Real person, fake name.

**For the record, I do Google guys but I never pretend I don’t. 🙂

Please note: I reserve the right to delete comments that are offensive or off-topic.

  • Most men enjoy female company and most men enjoy flirting. I find it difficult sometimes because I have a very quirky sense of humour which often results in me teasing my friends – male and female. Being incredibly slow in these matters, I only recently figured out that what I considered to be friendly banter and teasing was taken by some women to be flirtatious behaviour. It is very difficult to change a lifetime’s habits but as I am more aware of the problem, I am striving to change.

    At first, I thought “making things clear” – i.e. I’m not interested in a relationship – was enough but as Arlene says flirting (conscious or not) communicates something. As the sunscreen song says “Don’t be reckless with other people’s hearts; don’t put up with people who are reckless with yours”

  • possibility #3 he’s practicing on you to work up his courage to ask out the girl he really likes.

    • ::shakes head::

    • SVB

      Seriously, WTF? If that’s what he’s doing, that’s messed up.

    • Vegas Showgirl

      Or the guy that he does. I seem to attract a lot of gay and bisexual guys, and for some reason, they select me to practice romantic overtures on, then come out, and introduce me to their boyfriend.

      I’m not overweight or unattractive. Straight men like me, too. So as a woman I’m starting to wonder what gay and bi men would aggressively flirt with a woman for. It makes me doubt my own femininity, and that isn’t fun. I wish non-straight guys would… just kinda lay off.

  • I’m not convinced that flirting is communication in the full human sense. It’s more like an instinctual signaling. Like a male dancing spider that puts on quite a show to be sure that his potential mate won’t eat him. The problem for a guy is that flirting is inadequate to determine suitability and affinity: to figure out if he likes someone at a deeper level. For that, you need low stakes time together, conversation, etc. My wife tells me that she flirted with me at work before we got together, which frustrated her. Instead, a mutual friend told us both that we might be suited for each other. And then we started talking, and eventually went on a few dates.

    • Re: “The problem for a guy is that flirting is inadequate to determine suitability and affinity: to figure out if he likes someone at a deeper level.” — precisely! It’s a problem for women, too. Great point.

  • Anonymous

    Hi guys! Emily here. While I have pretty much taken care of the situation, I have enjoyed reading people’s comments and look forward to the guest post on this subject. To give you more background on my question:

    This is a guy who I’ve known for years, since college. For the longest time, I had a HUGE crush on him, but didn’t get the feeling that he reciprocated. Then, starting last spring, he started texting me, and our conversations were flirtatious. We actually went to a book signing, although I didn’t consider it a date as he never came out about how he felt, if he felt anything. I thought after the book signing things would progress, he started saying things like, “We should do this,” or, “We should do that.” Then, after the signing–nothing. He was incommunicado. Next thing I know, he’s in Orlando interning with Disney and dating a girl in his internship program. Then his internship ends, he moves back to Tampa, and I get a Facebook message from him asking for my number since he got a new phone. I send it to him, then we start texting again. And again, the conversations are flirtatious. However, at this point, I was pretty much over the whole situation entirely, and figured maybe I just mis-read his intentions, since not everything comes clearly over electronic communication. I didn’t think too much about it. We both like to read and talk about books, and he suggests meeting up to discuss books in person–like a book club. Last month we met at a bar, and again, I was going into it with the mindset that it was just friends meeting up to discuss books. The whole thing had a very date-like vibe, and I’m not saying that just because I’m a girl and he’s a guy. I like to think I’m pretty self-aware and can tell when I’m over-analyzing a situation, and I don’t think I was. Lots of flirting, and I could tell by the way the waitress acted that she thought we were together, so I know it’s not all in my head. But, as with last time, nothing happened. We were set to meet up this month, but I cancelled it. I’m not interested in flirting with someone who isn’t interested, and I figure if something was gonna happen, it would have happened by now. I just refuse to waste my time with something that’s not going to happen. I figure I can see him at outings with our mutual friends and keep communication to strictly text or email. Like I said, I’ve come to my own conclusions about the situations and have handled it accordingly, but I’m still interested to hear people’s insights and look forward to reading the guest post. Thanks, Arleen, for putting this on your blog, and thanks, everyone else, for the input! 🙂

    • Anonymous

      There might be various reasons good / bad or both why he’s acting like this. A lot depends, too, on things like whether he’s an introvert / extrovert, cultural background, real pressures or not in his private life, age etc ..
      It’s pretty impossible to give sensible “advice” over the internet over a specific scenario with two people you don’t know from Adam. What i would (with caution ..) suggest, is to ratchet things up a bit. Watch serious films together, talk about serious books, some serious experience you’ve had etc. If he feels uncomfortable by this, then question to yourself why (but he might really like you but is being let down by some personal trait). And if the opposite, again, has yourself why (is he playing games, still). But 99% of the hard word of figuring out will have to be done by you i’m afraid (from my personal experience of things ..)
      Best i can suggest at this stage! Good luck.
      Ed (UK)

    • Anonymous

      Thanks, Ed!

  • Anonymous

    From my POV, when i was in my early twenties, girls basically fell into 2 categories (yes, immature, i know):
    1) friends (platonic)
    2) sexual (not necessarily to have sex but to to play around in a sexual way – immature, i know).
    I’m a late developer in regards to this (confidence and emotional intelligence thing for me, at least), but only in my 30’s (bit pathetic i know) was i able to look at women as serious wife material (human beings, first and foremost, best friends, lover, partner, and mother all in one). Only then did i have the confidence / maturity. Up until then i was a boy in regards to these matters.
    I wish i’d grown up faster, to be more understanding / empathetic. I’m paying for it now in a sense, as i’m not married (never been), and single but have, at least had some serious g/fs.
    Girls: make it easier for boys, too. A lot of boys like me are not emotionally very intelligent. We need things spelt out loud and clear (so many guys just don’t “get” subtle emotional signals etc ..
    Ed (UK)

    • Anonymous

      Ok,so I am a 53 year old single female and I have this same issue. The flirting, the emails, the texts, etc. eluding to having a date but never a date! Buddy you are wasting my time. I hardly think at this point it is a maturity issue. This has happened more than once.

    • I wonder whether it’s just a male thing, regardless of age (no offense to males). One guy weighs in further on today’s guest post. I appreciate the honesty in the lot of reasons he writes why men might flirt but not go further.

  • I really like this post & you two are definitely adorable! I believe the aspect that some of the most relaxed & awesome dating games are the best 🙂

  • Patricia Taylor

    One reason…he’s already seeing someone. It’s nice to feel attractive when being flirted with and flirting back, but sometimes that’s all it is. Until someone makes a move, that’s all it is. Don’t make it something more.