Details, Part Five: In Which Agony Aunt Laura Troubleshoots Your Dating Fails

“Dear Agony Aunt Laura,” you say, “I screwed it up. A totally good dude asked me out and instead of saying yes, I let out this huge spiel about why I couldn’t go out with him, but I was just nervous and I didn’t really mean it and he’s really cute and now I’ve RUINED MY CHANCES FOREVER and I’m probably going to DIE ALONE and be found three weeks later half eaten by Alsatians. What do I do?” Or, “I’ve liked this girl for months but I didn’t know what to say and now I do, but we’ve hung out in groups so much that I know she’s put me in The Friend Zone, and now I don’t want to ask her out for fear of causing awkwardness. Little help?”

Well, I’ve got a twofer for you today, friends; a little advice for the ladies and the fellas. Guys, you first:

1. Waited too long and now you’re friends and don’t want to make things weird? Lame. Carpe diem, bro. Adults can be friends with people they asked out or went on two dates with. Asking a girl on a date is not a proposal. It’s not even saying, “I could marry this girl.” It’s starting an investigation. Like I said: is she interesting? Ask her out. If she says no, that’s fine. Just go back to being friends. (Ladies, this goes for you too; if a guy friend asks you out and you know his character and find him interesting, go out with, him for crying out loud!) The boundary between “friendship” and “romance” is porous. Don’t get so freaked out about the difference between girls-who-are-friends and potential girlfriends. Pick up the phone and make the call. Do it.

2. Flirted, charmed, complimented, sent long emails, texted with her until the wee hours, unburdened your heart to her, hung out with her in datelike situations, basically treated her like a girlfriend without actually asking her out? Brace yourself for some tough love, guys: You’re a jerk and you need to repent. OK, you might not be a jerk, but still. Repent. Because those actions say, “I want to win your heart,” but refusing to actually ask her out says, “I don’t actually care enough about you to think about how my choices influence you, and I’m cool with lying to myself about your level of heart involvement so I can keep getting my emotional needs met (but only on my terms).”

If you’re doing this (or some degree of this) right now? Then, hombre, you need to open a new tab and start composing this girl an email. I’m serious. Vamos. That email will differ depending on your situation. Do you actually like her and have just been a total bonehead about it? Tell her you’re sorry and want to start over by asking her on a proper date. Have you just been using her as a romantic placeholder until a hotter girl comes along? Apologize for your actions and assure her that you’ll be changing the way you behave towards her. And then cut that out. Next time you want a girl to act like your girlfriend, make sure she’s your girlfriend first.

3. General screwups merit an email, too, albeit a much shorter and less-serious one. Got all marriage-y/relationship-y on the first couple of dates? Keep the tone light, and tell her that you’re out of practice on this whole dating thing, you got carried away, and you’d like to assure her that 100% of the conversation on the next date will be about movies, food, travel, or music. Name-dropped all your semi-famous grad school profs — by their first names (or just generally came off insufferable)? Apologize for being a clod and ask for a do-over. Keep it to the point. No rambling, no excuses.

4. Listened to your bonehead roommates and waited too long to call after a date? Relax. Call her, apologize for the delay, don’t make any excuses, and then ask her on date two. (But, guys, don’t be shocked if she tells you she’s gonna pass. Many, many women have had a really painful, heartbreaking experience of being strung along at one time or another, so if she says no, it’s probably not personal, it’s just, you know, once bitten twice shy.)

Now ladies:

1. Wigged out when he asked you out? The only mature choices: cut your losses or ask for a Mulligan. Seriously. Call him up, quick, apologize profusely for being a stammering boob, explain that you didn’t say what you meant, and tell him that you should have said yes, of course. And laugh! Laugh at yourself! It’s funny! You’re ridiculous! You’ll tell this story someday and crack up about it anyway — why not start now?

2. Came across as high-maintenance, catty, ice-princessy, whatever? Email time. Short and to the point: “Hey, I really did have a good time last night and I realized after I got home that I acted ______________ when I really didn’t feel that way at all. Sorry about that! Chalk it up to first date nerves. Do-over?”

3. Worried that you’re leading him on if you’re not super into him at first? Please. Don’t worry about this until… like… date five. Besides, you’re not leading him on unless you’re acting like you like him when you don’t. Being open-minded and willing for your attraction to grow is just smart. As long as you’re having fun and are still interested in finding out more, keep going out with him. On the other hand, if your interest isn’t growing, don’t be afraid to call it quits. It feels fantastic to have a good guy interested in you, I know. It’s a little addictive. But if you know for a fact that you’re not into him after, say, date four, do the kind thing and move on (and go ahead and enjoy the fact that a good guy liked you enough to ask you out, girl).

4. Responded favorably to a dude who did what I mentioned in the guys’ #2 above? Ooh, child. Toughie. Been there. A man who does this is either not ready for a relationship or not a good guy. Email time: redefine the terms of your friendship (as in, back to “friends” rather than “OH GOD I LOVE him and I THINK he likes me but I just don’t KNOW ohtheAGONY”), emphasizing that you’re not going to act like his girlfriend any more without actually being his girlfriend. It’s not an easy step, but it’s so necessary. Again, short and to the point is best. Try to keep it to a paragraph so you don’t accidentally end up confessing your undying love to him. (What? Like that’s never happened to anyone else?)


Dating is awesome. Not only is it the best way to find a mate, it also gives you tons of life experience — getting along with lots of kinds of people, figuring out the opposite sex, being a good conversationalist, dealing with screwups and successes gracefully. It’s a grownup thing to do. So do it more, OK?

Fellas, I have a serious, legit challenge for you. Ask a girl out in the next week. In fact, make it a contest: challenge your roommates or work friends or the dudes in your small group to man up and ask a real live flesh and blood woman, someone you know and see in person, on a date. Whoever doesn’t, gets… I dunno, dogpiled or sucker-punched or whatever it is men do to people who lose these challenges. Or set yourself a challenge to ask one person out a week until someone says yes. I bet it won’t take nearly as long as you think. Y’all are awesome (seriously: I know some of you reading this are off-the-charts solid dudes) and you can totally kill it.

Ladies, I have a challenge for you too. Make it a policy to say yes to good guys. You need a better reason to say no than, “He’s only a barista” or “I don’t want to date guys who look like me” or “He’s five years younger/older than I am.” I’m talking about serious stuff, like “He dumped my best friend last week after dating her for six months,” or “He hasn’t had or looked for a job in five years” or “I find him absolutely, utterly unattractive both physically and personally.” Say yes. Really. Let that be your default answer, even if he’s not exactly your type, even if he’s “only” a barista/UPS box-slinger/T.A./waiter/still in school. You want the men around you to act like men? Then you act like a woman. Respond. Go on, what’s it going to hurt?

All right. I am tapped out on this topic for the time being. So go forth, y’all.


6 thoughts on “Details, Part Five: In Which Agony Aunt Laura Troubleshoots Your Dating Fails

  1. Agony Aunt Laura,

    Can I be the designated sucker-punch deliverer for the guys who lose their above recommended challenges?



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  4. It’s all very well to tell men that they have to be initiators and pursue women, but what stops me from doing that is that none of them are interested in me, and I don’t want to put myself through hurt and disappointment by having them turn me down, which has happened repeatedly in face to face approaches and also online.

    • Hi Ross, thanks for your comment! I composed a LONG reply but decided to turn it into a post instead because it turned out to be much, much longer than I thought at first.

      Your objection is by far the most common one among men. You are not alone in feeling that way at all. I do hope you’ll come back and read what I’ve written.

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