I was at my college reunion this past weekend, reminiscing about how many hills we had to climb to get to class, how many hours we spent sleeping on the desk in the library (which my mom never seemed to understand), and how many pecan pies we stole from the dining hall (my answer: one).  Ah… the good ol’ college days.

At the reunion, I ran into a friend whom I hadn’t seen in 10 years.  When I asked about his love life (I’m allowed to do that since my job is in the dating industry!), he told me he had been seeing a girl for several years, and she came to the reunion as his guest, so I got to meet her as well.

When his girlfriend left to get a drink, my friend looked at me with mischievous eyes and asked, “So, what are some of the dating questions men ask you anyway?”  I laughed because the questions run the gamut from things about texting all the way to sex… and everything in between.  (Please tell me you know there are things in between.)  A few of the more memorable ones are below, with my responses.


Shorts-lover in San Francisco

Shorts-lover in San Fran: Do I have to wear pants on my second date?

Erika: What?!

Shorts-lover in San Fran: No, I mean, can I wear shorts, or do I have to wear pants?

Erika: Are you going out to dinner? 

Shorts-lover in San Fran: Yes.

Erika: Then yes.  Wear pants even if it’s a hot day.  It takes the same effort as the shorts, but it looks like you tried harder.  Points for you.


Flummoxed Texter in Fargo

Flummoxed Texter in Fargo: How many days should I wait before I text my date to tell her I had a good time and want to see her again?

Erika: Text her the next day saying you had a great time and that you’ll call the following day to set up plans… and then actually call!  Bonus points.  (Double bonus points if you text her right after the date making sure she got home okay.)

Flummoxed Texter in Fargo: What if she doesn’t respond to the text?

Erika: I’d still call as planned.

Flummoxed Texter in Fargo: And if she doesn’t return the phone call?

Erika: Barring some unforeseen circumstances, she’s not interested.  Move on. 

Note: Women, if you are not interested, please do respond saying you didn’t feel a connection or some variant of that.  No one likes to be ignored.  The same goes for men.


Clueless in Coral Springs

Clueless in Coral Springs: Where do I take a girl on a first date?
Coffee or a drink.  Remember,
you can always add dinner, but you can’t take it back.

Clueless in Coral Springs: Okay, but where specifically? 

Erika: Ask what part of town is convenient for her, and then choose something around there.  Let her know that chivalry isn’t completely dead.


Dateless in DC

Dateless in DC: I don’t understand why I can’t get a second date.

Erika: How does the date usually end?

Dateless in DC: Sometimes a handshake, sometimes a little hug.

Erika: Do you ever offer to walk her home or wherever she’s going?

Dateless in DC: You’re supposed to do that?! 

Erika: Try this on for size… When the date is over, give her a little hug (handshakes are for business meetings) and ask if she’d like you to walk her where she’s going.  Whether she accepts will be a good indicator of whether she likes you.  And if you’d like to see her again, follow the advice for Flummoxed Texter in Fargo.  (I’m also not against kissing on a first date if the moment strikes!)

Do we notice a theme here?  In all of the scenarios, it’s the little confident touch at the end that makes the difference.  Whether that confidence is real – or you’re just “talking the talk” – it shows you know how to take control of a situation, not in a rude way, but in a decisive way.  If she is not receptive to you, she can decide that on her own, but you’ll know you’ve put your best foot forward by wearing pants, calling when you say you will, choosing a date place around her, and offering to walk her where she’s going.  None of these things takes very much time or thought, but the effects are huge.

After I told my friend all of this, he looked at me and said, “I had no idea!  I guess I’m lucky my girlfriend’s been with me for so long!” Don’t leave your relationship up to luck.  Little things go a long way.

Erika Ettin is the Founder of A Little Nudge, where she helps people navigate the world of online dating. Her services include: writing unique profiles to get you noticed, helping to choose your best profile pictures, writing one-of-a-kind emails to get someone’s attention, and planning dates. Want to connect with Erika? Join her newsletter for updates and tips.
  1. What a great article!! Can you advertise it more here, so all the men read it?? (smile
    And if you permit me to add just one more…you do cover it in the positive, I’ll go on the “don’t”. Please guys DO NOT ask for the lady to find a place she likes near her… If you are not sure because you don’t know the area, which has been the excuse I’ve heard a few times, you can always look it up online. Yelp always helps! You will make such a better impression, you have no idea!

  2. As Amorosa commented, this article is great. I do not agree with Amorosa’s comment that guys shouldn’t ask a date for suggestions for restaurants that are convenient for the date if he is unfamiliar with the area. If a woman holds that against a guy, two words: Red Flag. Don’t waste your time with anyone who doesn’t appreciate you asking for their opinion in a situation where they know best. Would you rather have a date pick a random restaurant in your area based on internet opinions that were likely posted by the restaurant management, or would you rather have some say in order to avoid the awful restaurants? Fellas, avoid the Amorosas of the dating pool. They aren’t worth your time or energy.

  3. Women, do you like talking about feelings on a first date or does that come off as prying or overly intimate. I’m genuinely interested in how people feel, and might want to ask, in response to a story, Wow, how did that make you feel? or, How did you feel about that? When I ask these questions, I usually don’t get much of a response. Should I keep it light on the first date and stick to questions about what do you like, where did you go on your last trip, what’s your favorite movie, etc.

  4. I agree with Amorosa about several things, that this is indeed a great article, and also Amorosa’s advice for the gents to do some research and at least suggest a location to meet.

    Bruce, I understand what you’re saying, and there is nothing wrong with asking a woman for her input, BUT… If you ask a woman to select the location, then you are putting the onus of the choice on her. We don’t know if you’re thinking of a meal or just drinks or what your financial situation is. Amorosa and I (and all of my friends) are saying, straight out: We are much more positivley inclined when a guy says, “Hey, I don’t know the area, but do you know anything about…” rather than “Pick a place.” You can now happily put that info in your arsenal and be glad that you can really make yourself stand out in a good way, with such a small gesture, rather than fault us for being honest.

    Bill, it’s downright refreshing that you are interested in how your date feels about various experiences, and I’m sure it flows more naturally in coversation, but when I read your questions, they sounded kinda of “clinical” to me; so maybe a little bit lighter at first.

    Good luck to all of you/us.

  5. These comments are all great! And, as a woman, I agree with what Dee said. If the man does not know the location well, he can suggest something based on research (women really appreciate that!), and she can propose an alternate of the same price/quality if need be. It’s the thought that counts. We don’t know if you’re asking us to pick a place because you’re really unfamiliar with the area or if you’re just lazy. Don’t let us assume the latter! 🙂

    And for Bill, I like your “feelings” questions, but perhaps something less like a therapist might ask and more like, “Wow – that must have made you feel amazing/scared/proud/whatever.” That way, she can agree or disagree, and you’re still showing that you care about her feelings.

    Thanks for reading!

  6. I think that if a man is willing to drive a significant distance to take a lady out on a first date, and he is unfamiliar with her area of town, it’s ok to ask the lady for a few suggestions. Then he can pick which one he would like from there. That way the man doesn’t end up picking the lady’s least favorite restaurant out of unavoidable ignorance.

    A man would knock my socks off if he asked me how I felt about a worthy topic. I like a man who is not afraid to listen to and talk about feelings. It might scare some women, but if you are the type of man who wants an emotionally open lady, then it’s a great way to weed out Ms. Wrong very quickly. However, some topics are not appropriate to discuss with a lady or man whom you just met. So, inquire about her feelings on those issues that are significant to you, and leave the more intimate questions for a later time. And, if you disagree with the lady’s feelings or thoughts, remember that a relationship is not about seeing eye to eye on everything. You never know…she might get you to think about something in a whole new light. So, don’t put her down for sharing her feelings, otherwise she might never share them again.

    When I go out on a date, I tend to spend significant time getting ready for it. I want to give a good impression and show that I put effort into the date. If a man wants to just take me out for coffee, a drink that I don’t enjoy anyway, it leaves me with the impression that all my primping and styling is only worth $3.25. Sorry gentlemen, but coffee doesn’t say that you are looking for a serious relationship. It says that you are looking for a cheap thrill. If you are a poor college student, coffee is fine. But if you are out of college, and are working and want to give a good impression, take the time to go out on a more meaningful date and show the lady she’s worth more than $3.25.

  7. Self-imposed rules can be quite frivolous and therefore maddening for others to comprehend. To wit: Amorosa’s ridiculous assertion that men unfamiliar with the area they’re traveling to should unilaterally decide on what to do and where to go. The cutesy comment about men reading this article is just another in a quiver of arrows sarcastically aimed at men’s alleged shortcomings; it’s insulting, smile notwithstanding. There is nothing superior about either sex, emotional, mental, or physical, and it earns NO advantage in attracting the opposite sex, since NORMAL members of the opposite sex will, as Bruce described it, see it as a RED FLAG.

    Self-absorbed attitudes are a reflection of the level of maturity an adult possesses. That so many men and women think they’re the center of the universe reveals a pathetic trend for a general lack of emotional maturity, awareness of others’ feelings and sensibilities, and ultimately is a confession of poor self-esteem/voraciously needy ego.

  8. can you tell me if it is still actuality that the man pay for the woman in the restaurant? the first time or later when they are going again?
    They are different advices about it.I am living in belgie

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