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Simply Solo Spotlight: 5 Ways To Win A Woman Over On A First Date

May 17, 2011

Today’s Simply Solo Spotlight is written by Lennie Ross. A former screenwriter for Playboy’s now-defunct film division, Lennie Ross writes a blog on dating in Los Angeles and has written a contemporary women’s novel entitled “Blow Me” which will be available this June on iBooks, Amazon Kindle, and Barnes& I hope you enjoy today’s guest post, and for my female readers, be sure to pass this advice along to the eligible men in your life!

Quick shameless plug: Do you have a story to tell? Advice to offer? Did you just have literally the worst date of your life and you must write about it? I’d love to have you as the next Simply Solo Spotlight! Contact me at:

5 Ways To Win A Woman Over On A First Date

first date, couple walking, heels

Love this picture. Courtesy of ~BostonBill~

First dates can be a drag: they’re stressful and anxiety-ridden. You could be the greatest guy in the world (and if you are, why aren’t you dating me?), but it’s important to realize that even if you’re excited about the date, your date might be a little nervous or apprehensive. Of course, you’re both hoping for a positive outcome, or you wouldn’t be on a date in the first place. But, you’re each walking in with your own BDB – bad date baggage. Try not to let it show and go in with a positive attitude. Gentlemen, here are a few quick tips to break the ice:

1. TELL HER SHE IS BEAUTIFUL: But don’t act surprised or stunned when you say it. Say it like you mean it, say it as a compliment, and say it matter-of-factly. This way you’ll come across both appreciative and deserving of her beauty. If you say it with too much intensity, she’ll get turned off and think yeah, way too beautiful for you! Whatever you do, don’t say it more than once on a first date or you’ll come off as the creepy, desperate guy or the player who just wants to get laid.

2. COMPLIMENT HER ON HER ATTIRE: That does not mean “nice dress” or “you look great.” She knows it’s a nice dress; she bought it. And she knows she looks great. She probably got a fresh mani-pedi, had her hair done and did her makeup to perfection for your date together. She invested a lot of effort in getting ready. So, invest a little effort in your compliment.

Comment on her shoes or her handbag, and if possible, ask her what brand they are or where she got them. This will not only give you a clue into her shopping patterns, and her ‘price tag’ so to speak, but it will also bond you like a girlfriend. Just don’t go too Queer Eye on her. Be sure not to say things like, “Nice shoes. They make your ankles look sexy,” because then she’ll think she has fat ugly ankles that only look sexy because of the shoes. Best to avoid the word sexy on a first date. It’s a little aggressive, and unless you know she is totally digging you, it just may just push her away.

3. EMPLOY PROPER ETIQUETTE: Nothing wins a woman over like manners and charm. Offering to pick your date up is still considered courteous, but don’t be offended if she declines – particularly if you met online. She is just protecting her privacy. Instead, offer to meet her somewhere convenient for her. A few basics that will definitely get noticed: stand when she stands, know how to use a fork and knife (don’t shovel your food in like you just got out of prison), help her with her coat, be polite with the service staff, don’t text or check your email at the table and pay for her valet parking. If you’re in New York, offer to pay for her cab.

4. BE HUMOROUS AND PLAYFUL: That does not mean be juvenile and recite stupid jokes. Don’t use too much sarcasm, either. Keep it light, positive and fun. Show her you’re not boring. If you don’t know how to do this, might I suggest you study a few cheesy romantic comedies before your big night, like Love Actually, Something’s Gotta Give, or virtually any 90s movie starring Hugh Grant.

5. ASK HER QUESTIONS ABOUT HER LIFE AND BE ENGAGED: Women have a perfected dating skill of getting men to talk about themselves, so the man feels good about himself and consequently the date. Be aware of this, because you men love to talk about yourselves and won’t even realize that you haven’t asked her about herself all night. If you fall into this trap, you may be deceived about how good the date actually is. She will likely think you’re a totally self-absorbed prick who didn’t have any interest in her. The trick is to realize that you’ve had the floor for a solid 10 minutes and turn it over to her by asking her about her career, her pets, her friends and family. Pay attention to her answers. Don’t just tune out the chatter. Repeat the names of her friends or family members or pets back to her when you ask her another question about them, so she knows you are listening.

In summary, relax, be yourself and try to have a good time. If you’re comfortable in your own skin, she will be able to relax and there will be more opportunity for sparks to fly.

12 Comments leave one →
  1. May 17, 2011 11:03 am

    The last line is key. In my single days, a date with a nervous dude never went well!

  2. May 17, 2011 1:20 pm

    Couldn’t agree more 🙂 My date last night told me my dress “looked lovely” and I was tickled pink. So easy… and yet so few guys manage to master the basics!

    • May 17, 2011 3:06 pm

      Thanks Kat & Tori, appreciate your feedback. Glad to hear my tips make sense. I just hope a few men read the blog! Lennie xo

      • eternallyemo permalink
        May 17, 2011 9:51 pm

        You got one here! I’ve been known to overdo things on a first date and then get a little lazy on subsequent dates, so I am definitely taking this to heart. Thanks for reminding me not only *what* to do, but to what extent. Very helpful!

  3. Claudia permalink
    May 17, 2011 11:26 pm

    Very good list of what not to do.

    However, the do part would entirely depend on the type of person you are trying to win over. 4 and 5, yes. 1, 2 and 3 are much further down on my list.

  4. May 19, 2011 10:51 pm

    I don’t think I did any of the above 5 things on my latest first date (with my now girlfriend).

    However, I DO know all 5 were present (in one form or another) on the second date we had roughly a week later.

    Whew. That was a close one.

  5. May 21, 2011 11:15 pm

    I’ve got to agree with Tori …the last tip is KEY. My experience has been that men don’t ask questions … they like to do the talking. To me not asking questions about me = not being engaged in the conversation, which means umm, that maybe they’re not interested in getting to know me. At least that is my perception of not asking questions. I’m still single and waiting for someone to ask questions. 🙂

  6. May 22, 2011 12:43 am

    I’d rather he didn’t do #1 & #2 for awhile.
    which is precisely what dearie didn’t do to me for first few months. I would have thought he was nuts. The older women get, the less plausible some of that becomes…the lines become..old. Unless she genuinely dresses up well for a special occasion.

    Manners at any time are always nice. Even when you are together permanently.

  7. May 22, 2011 12:45 am

    Sometimes the best thing is to be with her if she is having a rough day.

  8. June 1, 2011 4:17 pm

    Cool post. Mind if I link to this in my blog?


  1. Link: Simply Solo Spotlight: 5 Ways To Win A Woman Over On A First Date « Heels and Hiking Shoes

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