I’m writing to you to get your input into when a guy should ask a girl for a date after initially meeting them. To get a bit of context on myself I’m mid-twenties, not from the USA, never been on a date, etc. I do spend a lot of time online on blogs like yours or different subreddits just researching and reading about relationships. Something that I see a lot from women is that they don’t want to be put into the “girlfriend” zone, for a guy wanting to be their friend just to sleep with them, so I tried a couple of different approaches with the women I met.
First woman I asked for a date was around a month and a half after meeting her weekly for a hobby class, she answered me with “we shall see”, I never brought the question ever again because I don’t want to give desperation vibes and four months later neither did she. Probably that was her telling me a nice “no”. What I observed is that before asking her out she was nicer to me, more touchy, was looking and smiling in my direction a lot more, afterwards she went very cold and distant.
Second woman I waited a bit more after meeting her, we talked a lot, she would sometimes initiate texting, we could talk for hours without awkward silence. Also caught her taking pictures of myself without me knowing when we went with a bigger group to a cabin for a weekend. I thought there was something so I asked her if she wanted to meet for a coffee, but did not use the word date like I did with the first girl. This was around 4 months after first meeting her. She accepted it, during the meeting I did nothing to imply this was romantically. Same for the second (activity) and the third meeting (lunch), I was too scared and had no idea how to initiate physical contact with her or move the conversation into that direction. When I asked for a fourth time I wanted to confirm it so I finally asked if she wanted to go on a date and her answer was that she does not see me as more than a friend. That sucked but what can you do.
I know that I generalize but I did both warm and warmer approaches and both failed. In general, should I ask for a date even faster? Should I always imply I’m asking for a date? From my stories what should I learn?
The Very Confused Guy
Alright VCG, what you’re asking is a little more complicated than I think you realize, but I’ll untangle it for you.
First and foremost, you’re making a mistake that a lot of guys make when they’re starting out or somewhat inexperienced: you’re looking for hard and fast rules, and there really aren’t any. While there are lots of folks — especially in the dating advice community — who will lay down rules for what you absolutely must or must not do… but as the sage once said, they’re more what you might call “guidelines” rather than actual rules. After all, you’re gonna get far fewer clicks for saying “Well, it depends…” or “you need to read the room”
But since women aren’t a hive mind or a computer program that follows strict algorithmic scripts, you’re going to run into plenty of times when someone “breaks” the rule and succeeds or when following the rule fails miserably.
Now this doesn’t mean that the guidelines are useless, especially when you’re just starting out. In fact, they can be very helpful… but part of the point of them is to help you develop your social calibration. The more work at developing your social skills, the more you train yourself to be able to read the situation and gauge what you should do next. That means that there will be times when you’ll see a moment that, according to “the rules” would be the worst possible time to ask somebody out… but you’re picking up enough signs that you’ll decide that it’s worth giving it a shot anyway. Sometimes that gut reaction will pay off, despite being the “wrong” move. Other times it won’t… and in those moments, you learn, you recalibrate and you try to figure out what went wrong and why.
Part of the learning process, incidentally, is to look at the context of any rules or guidelines; those make a significant difference in how you apply them. Take, for example, what you read about women not wanting to be put in “the girlfriend zone” by guys. What they mean by that is that a lot of guys hide their intentions or act like friends under false pretenses. They’re Nice GuysTM who try to surf the ambiguity wave, inviting women out on activities that may or may not be a date, only revealing which it really is later on. They act like they’re friends, when in reality, they’re trying to worm their way into her heart and pants and never wanted to be friends in the first place. That’s radically different from when you’ve known someone for a while and start to develop an attraction to them. The former is fundamentally dishonest; they’re deceiving the women they’re hoping to date by concealing their true interest. The latter is… well, how a lot of relationships develop, honestly.
Now, one of the things I always suggest is making your intention clear from the jump. That means that if you’re interested in someone as a potential date or lover rather than a friend, you want to act like it. That means being willing to flirt, show that you’re attracted to them and — critically — ask them on a date. Not “to get together” or “hang out some time” but an unambiguous date. This helps you avoid confusion, as well as keeping you from investing emotionally in someone before you have reason to do so. After all, if you spend weeks or months pining for someone but never actually doing something about it… well, all you end up doing is investing your time and brain cycles on them and building them up to a being of great and terrible importance. So by the time you’ve actually developed the courage to ask them out, the potential rejection becomes much much more painful than it would be otherwise. Betting told “no, thank you” hurts far less when you haven’t waited weeks to get there.
It also means that you don’t end up in situations where women think that you were faking your friendship with them. You know that you were just trying to work up the guts to ask her out. She, on the other hand, has known too many guys who tried to leverage their “friendship” into sex or thought they put enough Nice Guy tokens into the machine and sex was gonna come out. That’s not your fault, but it’s still a situation you have to acknowledge and deal with.
The obvious issue here is: what if you aren’t interested in them as a potential romantic or sexual relationship at first? Well, the same basic principle applies: you want to make your interest known earlier rather than later. That is, when you recognize that you’re attracted to them and intend to act on it, you make it clear. This is where honesty and directness is important; you want to say “hey, I really like what we have but lately I’ve been interested in something more with you. If you’re up for it, I would love to take you out on a date and see where things go. If you’re not feeling it, that’s totally cool and you are more than welcome to tell me no.”
That last part is important; inviting the ‘no’ helps avoid putting pressure on her and helps mitigate potential awkwardness. It also lets her know that this isn’t a “I’ve been biding my time for this exact moment” situation; you’re letting her know that your feelings have changed and you want to see if she’s on the same page or not.
With all that in mind, let me unpack the two examples you gave in your letter.
I want to start with the fact that you’re actually making solid progress. The fact that you’re actually asking people out is good. I think you could’ve done things a little better, but overall, you didn’t do anything wrong per se. I think you could have done things better, but learning from this will go a long way towards getting better results in the future.
I also want to point out that I don’t think that the way you asked them out or how quickly you asked them out would have changed things. In both cases, I think it’s fairly clear that while both women liked you, they weren’t attracted to you as a potential boyfriend. However, when you asked and the way you asked likely affected how things played out.
In the first, the biggest issue at hand is that she likely thought that, yes, you were “girlfriend-zoning” her, which would explain the coldness from her. I’m a big proponent of meeting people organically through hobby groups and meet-ups, but a lot of dudes try using those groups as their personal dating pools. They’re only in that club (or yoga class or…) to hit on people or pull Nice GuyTM shit. A lot would also depend on how you acted after you asked her out. One of the things I always tell guys is that people will take their cues from how you act. If you act like everything’s normal and this isn’t a big deal, they’ll respond accordingly. However, if you were giving her sad puppy eyes, coming across as clingier or more intense than before, that can send messages that can be misinterpreted.
Since I wasn’t there for that part however, I can’t say for sure; you’re the only one who can gauge that. It’s something to be mindful for the next time.
In the second case, I think the fact that you didn’t make it clear that these were dates is what dragged the whole process out. If you had, I think you would’ve gotten your answer much earlier. While that likely wouldn’t have changed the outcome, it would at least mean you got your answer and would be free to go meeting people who are into you. As it was, I think the lack of clarity dragged things out further than was necessary and made things more painful and awkward for you.
I do want to point out that I think part of the issue at hand was that you misread friendship as romantic interest. A lot of what you describe about her behavior doesn’t read as attraction to me; it reads as fairly typical behavior from friends, especially from female friends. Men and women are often socialized to treat friendship differently; male friendships tend to be activity based, where female friendships tend to be about spending time and sharing with each other. For guys who aren’t necessarily used to how women act with their friends, this behavior can be misinterpreted as as interest, rather than… well, just being friends. Making it clear you were asking her out on a date early on would have cleared this up a lot sooner than it did.
That having been said: if she was interested in you romantically, then the fact that you didn’t demonstrate any non-platonic interest — no flirting, no going for the kiss, etc. — would have told her that you weren’t interested in her or only thought of her as a friend. So after three hang-outs where you behaved like a friend, she likely would’ve gotten over her interest and settled in to being friends.
All in all, you’ve got room for improvement, VCG, but you’re doing well. Those first few times out are always going to be a bit rough, but you survived and you can learn from these. Take what you’ve experienced, learn from it, and apply it to next time and you’re going to have a much better outcome.
Keep at it, and you’re gonna have a great time as you improve. You’ve got this my dude.
Hi Dr. NerdLove
I am 39 year old man in love with a 26 year old woman that I have been friends with for the last four years. Over the years that I have interacted with her, I slowly fell for this girl, until one day about a year after knowing her I realized I was in love with her. Despite the age gap (12 years 9 months), I have many things in common with her. Similar taste with food, political leanings, books and movies even personality quirks and traits. The differences with her appear small little things like pet preferences (not a big deal for me), except for the age disparity.
There are times I think she appears to be attracted to me: the way she says hi to me in lower soft tone of voice sometimes, the way she talks to me in a shy manner compared to others or even laughing at my jokes. She recently broke up with her fiancé of five years as of a few weeks ago and has expressed the idea of not dating for a while. I don’t know if I should act now or wait it out a little. I am also afraid she will reject me because of the gap and thus damage our friendship. Should I wait it out, make an attempt, or try to move on?
Hopelessly in love
This is a classic case of “the problem you’re asking about isn’t the problem you actually have”, HIL.
First and foremost: an age gap between someone in his late 30s and a woman in her mid 20s isn’t that big of a deal. The things that make age gaps problematic is less about the difference in age per se and more about what that gap represents. Part of why people side-eye Leonardo DiCaprio, for example, for consistently dating younger women is because he seems to treat 25 as a cutoff date. That suggests that he wants women specifically because they’re younger than him and that he sees 25 as being the point where they’re no longer attractive to him. Even if we’re interpreting this as generously as possible, that’s pretty sketchy. It ties into a lot of fucked up messaging about women’s value and attractiveness being tied to their age and that older women are less desirable because they’re older. Seeing as there aren’t any alternatives to the linear progression of time, that means that literally every woman’s value vanishes at a certain point.
There’re also issues about power and influence. A 30 year old and an 18 year old gets a lot of side-eye because of how much more social and cultural influence the older partner frequently has. Now to be sure: when someone’s 18, they’re free to make whatever choices they want and date whomever floats their boat. However, the power dynamic can be significant, and could lead to someone feeling pressured to agree to things that they would not otherwise agree to.
(Notice very carefully I said can and not is; as always, things can vary widely on the individual level. There’re plenty of folks who dated people much older than they were and found the experience to be valuable, enriching and important and have nothing but good things to say about the relationship.)
However, as people get older, age differences mean less. Jokes about adulting and extended adolescence aside, someone who’s in their mid-20s is usually fairly well established and confident in themselves. They tend to have more life experience than your average 18 year old and have a better grasp of who they want to date, what they will and won’t put up with and are more empowered to leave a shitty situation.
So no, I don’t think the age gap is a big deal in this case. If nothing else, her being 26 puts her squarely within the “half your age plus seven” rule of thumb.
The problem you have is two-fold. First is the fact that I think you’re experiencing some dickful thinking. The way she says “hello” isn’t really a reliable indicator of interest, nor is talking in a shyer manner. I think you’re taking normal behavior and rounding it up to interest because you’re hoping she’s interested. It’s a lot like when guys with Oneitis try to parse the exact word choice their crush uses; the more nitpicky and granular you get trying to find “proof” that someone is into you, the lower the odds are that she’s actually interested. If you’re down to reading meaning into the tea leaves, then you already know how she feels. You don’t like the answer, so you’re shaking the metaphorical magic eight ball to get a different one.
(Yes I know I just jumped metaphors. Keep up.)
The second is… dude, she just broke up with her fiancé. Even if there were some interest on her part, she was with the guy for five years and engaged to be married. If you roll up on her and proclaim your love for her, you’d be telling her that you’re less concerned about her and more about establishing a claim while the “window” was still open. A break up is rough, even when its amicable, especially when they were planning a wedding. Under the best of circumstances, that takes time to heal and means she’s almost certainly not going to be interested in dating anyone any time soon.
Plus, y’know. She told you that she’s thinking about not dating for a while. This could be the literal truth, or it could be that she knows you’re interested and is giving you the wave-off. Either way: you need to take her at her word on this.
My advice? Let this one go. She may be awesome and all, but there are other women out there who are just as awesome if not moreso, who will be into you and who aren’t nursing a broken heart. If your friend decides she’s interested in you, she’ll let you know. Unless and until this happens, it’s better to move on.