“How can I get 26 dates in 26 days?” —Alisa’s advice

Since you are the “Dating Coach,” I just wanted to ask you what you think about this idea. I want to go on 26 dates in 26 days. What would you suggest to help me succeed at this goal?

Thanks for your help,

Ms. Daring

Dear Ms. Daring,

As long as you keep your faith and have fun, what can it hurt? Here are my suggestions. Set a goal every week to tell ten men, “I need to go. I would really have liked to have gotten to know you better, though. I would love for you to call me sometime.” Then smile and walk confidently away. If he’s interested he’ll stop you and ask for your number. He might even seek you out on Facebook, especially if you’ve mentioned that you have an account.

I’d also suggest that you do little things every week to support the process: call your friends and family to let them know you are open to blind dates, set up an online profile on a dating website (and then change the picture a few weeks later if you aren’t getting results), seek out men on Facebook that you haven’t seen in a long time. In each of these situations be sure to say, “I’d love for you to call me sometime” whenever you can.

Have fun with this. Record both your efforts and their responses. Don’t focus so much on how many dates you’ve had; focus instead on how many times you’ve been able to say, “I’d love for you to call me sometime.” Then, as a side note, see how many dates come afterward. Be sure you don’t water down this sentence. Use these exact words. This is what men really want women to do and say. If you act feminine and confident, they’ll love it. Furthermore, it’ll give you more opportunities to practice and to improve your techniques and your ability to deliver these words with femininity, warmth, and confidence.

Don’t expect great dates, though. Just look forward to having dates and lots of opportunities to work on your skills while on the dates. If you feel uncomfortable or threatened, however, never take a date. No goal is worth compromising your safety or lowering your standards in a way that puts you at risk of falling for someone who is totally wrong or bad for you. I hope this helps. Please come back to this page and give me updates about how it’s going in the comments section below.

Thanks and good luck,



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14 thoughts on ““How can I get 26 dates in 26 days?” —Alisa’s advice

  • I know I didn’t write the question but I appreciate the advice! It’s hard for me to find that many guys to say that too though. I’m 30 and it seems like the older you get, the harder it is to find good, single men my age. I don’t really trust the internet for finding guys. I’ve done it before and always find men to be way too forward or completely weird! I have asked several people to set me up but I will look through my contacts again. I’m just wondering if anyone has any idea where the older men are??? Thanks!

  • Thanks for the advice. I’ll practice my technique and will set some goals each day to say “I’d love you to call me sometime” and record how many of the 26 dates come from those words. What are your thoughts about sharing with these guys what I am doing? What about Asking them out during this social adventure, for example, I have a day open and will need to fill it with a date, could I talk to a guy/call a guy and say “If you’re free Wednesday night I heard about ______ activity and I really need someone to come with me, I’d love it if you could go with me? What are the thoughts about that situation? I am prepared and un-afraid to do this, but just want to do it in the right feminine/flirty manner. Besides, aren’t they my hero for coming with me?

    Thanks Alisa

    • If you ask men out, be very feminine about it. “I have this thing I am doing and of all the guys I thought of I know you would make it the most fun. Would you go on a date with me to _______?” If he says “yes” then say in a warm, feminine way, “I know I asked you out and I plan to pay for the date, but it would really mean a lot to me, would you pick me up for the date?” Then during the date touch him, ask for help, tilt your head, fluctuate your tone, give compliments when he treats you well. In other words be sure you act feminine and treat him like the man.

      I hope this helps.


  • I thought I’d offer a male’s perspective on this topic (while recognizing that not all males might see things the same way I do).

    To Sadie, I think it really would be difficult in our early thirties to find either the 1) time or 2) the actual “candidates” to go out on 26 dates in 26 days. I think those are just two of a number of logistical constraints of dating at our age to keep in mind.

    From my perspective, I appreciate that a woman shows subtle interest when she’s interested. I don’t think, however, that you should be discouraged if only a few of the many lines you cast out actually get a bite. I, for one, would need several, repeated indicators from the same woman before I took the step to ask her out–to mention nothing of the fact that I’d want to be interested in her, too.

    In my experience, a woman who shows subtly consistent (but non-aggressive) interest starts to eat away at me and I start to think, “Wow! I’ve really got to find a way to spend some time with her.” But I think I’m past the stage of being able to go on many, frequent dates based solely on casual interest.

    To Ms. Daring, I, for one, would feel a little used by “I have a date to fill.” Rather than sounding cute and fun, it sounds self-aggrandizing. Maybe that’s just me. I might be the exception rather than the rule. I wish you well in your quest, nonetheless!

    • Well put SLC 84102 Guy.

      I’m going to go out on a limb and assume that Ms. Daring is the same girl I know. I did go on a date with Ms. Daring as one of the 26 dates. I didn’t feel used. I was up for being part of her adventure and found her to be a very genuine, fun, and charming. I look forward to my next date with her.

      In the end I believe that the way we treat each other on dates is what leaves the lasting impression independent of what brought you together.

  • I agree with Sadie’s comment. I’m a divorced single mom approaching her thirties and I rarely am in social situations where I get to casually meet and interact with single me. I would love to have more practice using my female powers of persuasion, but when?? I’ve done the online dating thing, but it seems that the kind of guys I meet on there have been sub par and I’m a little burned out. What suggestions do you have for Sadie and I?

  • Dear SLC 84102 Guy,

    There is more to the story then me just trying to get 26 dates in 26 days. It does sound quite ostentatious when you hear just part of the story. I am being sincere in my desire to get to know 26 different people. I’m not doing it just to check the box and fill a date as you say, rather then to just be optimistic, have fun, and get to know 26 different people. I don’t have any expectations other then the fact that I do expect to enjoy many summer nights with different interesting and wonderful good men. I personally don’t see any harm in being sincere in me wanting to get to know many different people in a short period of time. I’d rather take a risk in doing something different and fun then sit home feeling sorry for myself in this never ending time of singleness. Life is to be lived and experienced. If you don’t believe me, I have an opening on date 17 :).


    Miss Daring

  • I am a single mom too (and a friend of Melissa’s). My question is a little different than Melissa’s. I am just recently divorced and am not ready for a relationship. However, I would like to attend singles events to have fun and meet both women and men friends. How do I send the message that I’m just looking for friends now but want to date in the future? I don’t want to end up with a bunch of guy friends who see me as ‘just friends’ a year or two down the road when I am ready for a relationship.

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