You Are Brave Enough To Ask A Lesbian Out.

by Mary Gorham Malia

“You are so brave to walk up to me and say hello.”  I hadn’t been thinking bravery was required to ask a lesbian out but two women said this to me at Provincetown this week. It was a surprising comment to me. How else to you get to the place of asking a lesbian out.

Screen Shot 2012 10 12 at 1.25.43 PM You Are Brave Enough To Ask A Lesbian Out.

Here’s the back story. It’s Women’s Week in Ptown.  Hurrah!
There are events going on non-stop from 8:00am till 1:00am everyday for the week.
Add to that a thousand women showing up and you’ve got a lesbian happening that is ripe with the possibility of meeting someone.
If you’ve been reading here a while, you know I’m single. I don’t write about myself that often cause… yawn… that’s boring. But my single status has come up lately so I’m plowing ahead.
I spied a woman at Pied Bar on Tuesday evening.I found her to be attractive, with great style and a great smile. A few things that attract me.
I have to admit, how a woman dresses can draw my initial interest or repels it.  Now how you dress is personal to you, so always stay in integrity with how you present yourself. Heck you knew that already right?

You can be brave too, because to get to a date, you have to ask a lesbian out.

Yes, I want to have a great relationship. Making that happen takes a commitment to the process of dating. To get to a date, you have to ask a lesbian out. Right, I know you know this but do you do it?

We all know women that are attracted to the more feminine type, or sporty dyke or butch and all the variations in between.

I decided to introduce myself as it seemed she was single. She was dancing and then walked up to the bar to get a drink. I approached her at the bar. Stuck my hand out, smiled and introduced myself. “Hi, I’m Mary. I noticed you earlier this evening and though what a great smile you have. I wanted to introduce myself to you. Are you here with friends?”

You Are So Brave to Approach a Woman and Say Hello

After we talked for a few minutes, she said, “You are so brave to approach a woman and say hello.” Really I was nervous about it but I’ve learned that a friendly approach almost always gets a friendly response.

We had a fun conversation. I asked her to join me for coffee in the morning. She said she’d think about it, so I gave her my number and didn’t hear back. Oh well… moving on.

If someone is a “no show” or non-responsive then my answer to that is, I guess she isn’t the one for me.  No harm, no foul, move on.

Two nights later I’m at another event. I see another woman, someone I haven’t seen all week. Again, I find her to be attractive, great style, great confidence and of course a great smile.

I tried to find her to talk to in a crowd of women and she sort of disappeared. So I left the event to head back to Rose Acre Cottages where I was staying with my friend Kim.

On the way down the street, I said a little prayer to the universe. It went something like this: “Universe, I’m putting myself out here to find love and relationship. I’d like to meet the woman I saw this evening and if she’s a possible match for me how about you put her in my path so I can introduce myself.”

Two minutes later, I round a corner and there she is walking toward me with two friends. I looked up at the sky and said, “Ok, Universe. You’ve done your part, now it’s my turn. I said I would, so Ok here I go.”

Since this woman had been part of a singing contest, I used that to say something to here.  I walked up to her, stuck my hand out and said, “Hi, I’m Mary and I really enjoyed your song.” She and her friends stopped and talked to me for about 10 minutes.  I knew her name from the contest but for this article, I’ll call her Debbi.

We laughed and talked about the singing contest, she introduced her friends, we shared a little about our being in Ptown. Her friends offered up that Debbi was in Ptown looking for the love of her life. Hmmmm…

How interesting I thought, me too. I just didn’t say it. They also offered up that she was interested in spending time in Maine. Hmmmm… also very interesting. Debbi is from another part of the country.

It’s one of the fun things about Women’s Week is that women come from all over the world for this event. And because they’ve come so far, most are really open to talking to friendly strangers.

Anyway, back to my story. Debbi’s friends make the comment, “You are so brave to just stop and introduce yourself.” I’m thinking no I’m not, I’m committed to meeting single women so that I can meet Ms. Right for me.

I’ve made a commitment to myself and I’m going to follow through on it. When opportunities show up to meet someone I might be interested in. I take action. I make myself do it.

Think of life as having three simple rules:

  1. If you do not GO after what you want in life, you will NEVER have it.
  2. If you do not ASK, the answer will always be NO.
  3. If you do not step FORWARD, you will always be in the SAME place.

These aren’t just great rules for life, they are great rules for dating. If you don’t do something different in your dating life, you will keep getting the same results.

If you aren’t asking anyone out how is anyone ever going to say yes to you.

If you are always waiting for the other woman to take action and do the asking, then really girls… shame on you for not owning your power and your life and your happiness. Get off your butt and ASK!

Oh and about Debbi, we couldn’t make coffee work, but she did call me this morning and we had a lovely conversation. I’m sure there will be more to follow.

Being brave is so worth it. Go for it. Be brave. Ask… because you have nothing to lose and the whole world to gain.

Does asking a woman out scare you? What scares you the most? Share with me your thoughts in the comment section and I’ll keep writing about this topic for October.

Warm hugs and much love going your way!

MGMsignature You Are Brave Enough To Ask A Lesbian Out.

profile pic 300x300 You Are Brave Enough To Ask A Lesbian Out.

Mary Gorham Malia is a gay girl who’s passed the age of 50, survived menopause, hot flashes and night sweats, raised two children, came out later in life and divorced, grew from being a baby dyke to a lesbian with many dating experiences, has been rescued from cubicle nation and now finds the wisdom of being a bit older as the salvation she always wanted. She’s gone from being lost and late to lesbian life to being a seasoned life traveler who has a commitment to reach out to the lesbian nation and make a difference for lgbt women.

Her business, Gay Girl Dating, LLC, was founded on the belief that lesbian, gay, queer, bi and transgender women can live extraordinary lives when they understand the principles and practices that make life great and put these practices into action in their own lives.

Gay Girl Dating Coach, LLC | PO Box 10924 | Portland, ME 04104 |

| Office: 512-544-7494 |

© 2012 Gay Girl Dating Coach, LLC
Unauthorized duplication or publication of any materials from this site is expressly prohibited.

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{ 22 comments… read them below or add one }

Janet October 15, 2012 at 11:58 AM

My Mother taught me “always ask all I can say is no” ….I have used that statement throughout my life…..Janet


Felicia October 15, 2012 at 11:47 PM

Hi Mary,
I have been enjoying your articles and most especially this one. Yes it is scary to me to ask a woman out. I’d have to state the obviius fear is rejection. How about this? I am attracted to my psychology professor and I kind of feel a connection. I know that it would be a serious conflict of interest. I’m feeling brave enough to approach her at the end of the semester. I would vow never to take another one of her classes. Your thoughts would be appreciated. Wishing you well; keep up the good work!! I was a lil trigger happy with the previous comment; please disregard.


Flo October 17, 2012 at 5:08 PM

Mary, you have a great smile! If I was in your location I would indeed introduce myself.
I often see women who interest me, but have not ventured forward. Well, not this year! I did last year but did not follow through with my interest.
I know at some time I will meet someone who is interesting and am confident that I will then take the occasion to make a new acquaintance.


Legs November 7, 2012 at 12:01 PM

Hi, Mary!

I walk up to women if I’m attracted enough and catch them alone. Often, I see them on the dance floor with friends, don’t know what to do about her friends, wait for her to move to the bar, and… ah, off I go! That doesn’t happen often, though. Most times, I’m looking at a girl dancing with her friends, and I’m thinking, “OMG, WHY DO THEY ALL STAY TOGETHER ALL THE TIME? Give room for others to chat you up or ask you out!!!” I know the problem must be my own – not having the guts to walk up to a group of friends. Maybe I’ll try what you’ve said here, though… Go up to a girl and talk to her AND her friends and introduce myself honestly… :)


Stephanie November 12, 2012 at 8:19 PM

What scares me? I’m a 19 year old college student. I can’t go to gay bars. I have no idea how to tell if a girl is gay or not!
It’s awful…


Iris January 4, 2013 at 7:28 PM

I feel the same way.


Tasha May 8, 2013 at 2:21 AM

Same here. I’m 21 and this year I started falling for a girl and I realized I am attracted to girls too. But I just can’t tell if a girl is gay or not! :(


Reghan December 31, 2012 at 3:07 AM


I just turned 56. During the past three years, I’ve been single. I have my dogs, my friends, and my writing, so I’m never really lonely. Writing is a solitary vocation. I’m really happy with my life right now. I feel like everything is back under control. I’ve righted the ship (after the disaster that was my last relationship). So I’m hesitant to screw that up.

There is someone in my life who I believe is interested in me. She’s admitted to flirting. I haven’t responded because, until recently, we had a professional relationship which precluded anything like that. She’s smart and funny and easy on the eyes. We seem to have some things in common, and the same sense of humor. She’s close to my age, and has a responsible job which allows her to support herself. Better yet, she came to a holiday party at my house recently, and my friends like her. In other words, she’s pretty darned close to perfect. But I’m terrified to ask her out — not because she might say no, but because she might say yes, and one thing could lead to another, and before you know it you’re clearing out half your closet. In my experience, relationships have meant stress and heartache — if not immediately, then soon enough and for way too long. (I’ve made some horrible choices. I don’t regret them because, as I said, I’m pretty content with where I am. But I’m not looking for an encore, either.) Also, the woman I’m interested in just got out of a long term relationship, and the ending was ugly. It occurs to me that I could be the rebound relationship.


Mary December 31, 2012 at 7:39 AM

Hi Reghan,
It’s a wonderful thing when a woman can say she’s happy in her life and being single isn’t a curse. Congratulations on finding that balance. And yes,then someone comes along and upsets the balance of our life. In part, that is just how life words and always will. Life is about ebb and flow, stasis and change.

About your friend, you are right you may be a rebound. But what if you just took it slow! Don’t rush into dating, don’t rush into sex, don’t rush into moving in. The biggest mistake we make in relationships is making commitments way too soon in the process.

If you’re life is really so great, don’t change it. Just go slowly and see how she fits into the life you live now. No need to make room in the closest either. You aren’t a kid, you know what the gig is about. Go slow.


Christine January 4, 2013 at 4:00 PM

Wow, I just found your site and I am so glad that I did. I feel so brave even just writing this comment…At 41, I just fell in love with a woman–not for the first time in my life–but finally a lesbian woman for the first time. Being in straight relationships with men for my life, but constantly falling in love with straight women who are unavailable (since they are the only ones in my social circles), has kept me closeted as bisexual for so long. By a glorious fluke of a rental-sharing situation, I found myself making friends with a group of lesbians 10+ years younger than I am….I fell radically, nuttily in love with one of them (11 years younger). She has no clue, so I think…How does a woman come out in this situation without looking like a bi-curious middle aged Cougar on the prowl? While I could pursue this woman, it terrifies me, since I want to retain her friendship above all else and not weird her out with our age difference. And, if push comes to shove…where do I start looking for lesbian women my age so I can escape this mental love trap of loving someone a generation younger than myself? Your advice throughout your website is so grounded and amazing…I think I found just the resource I need. I am so glad you are OUT there! :)


Caracae May 17, 2013 at 6:22 PM

The thing that makes me really cautious is that I like women who might very well be straight as far as looks are concerned. How does one approach a woman outside of a typical lesbian setting?


CinnamonGirl September 14, 2013 at 3:49 PM

If she’s straight she will probably think your being a really friendly woman and promise you she will not suspect your interest. If she is attracted to women, she will either be open or closed. Women being women , straight or lesbian are generally weary of people whose attention they don’t want. Its pretty clear with a dyke I find – its either yay or nay. Open to being corrected if I’m wrong.


CinnamonGirl September 14, 2013 at 3:43 PM

I absolutely adore this 52 year old woman who was my supervisor 3 years ago. I’ve now completed my training and a fully independent professional. I met her when I was 34 and thought I was straight. She found out I was straight. 3 years later I’m clear about my sexuality and that I want to spend my life with a woman. How does a 37 year old woman ask an outwardly serious 52 year old woman ( who is a semi-closeted lesbian) out for coffee/drink ?


Light Saber Princess October 5, 2013 at 8:26 PM

I’m so glad you exist! I’m a 20 (soon to be 21) year old woman. I have been madly in love with one of my college lecturers for almost 3 years now. She won’t be teaching me anymore very soon and I wanted to wait til I graduated to ask her out. She’s a lovely human being with an amazing soul, and she’s an outspoken feminist. I’m terrified out of my mind to ask her out though. I fear rejection way too much. I don’t know how to handle this.


Mary October 6, 2013 at 2:06 PM

Dear Light Saber College Student,
I often hear from women who discover they are lesbian because they’ve fallen in love with a college professor/aid/etc. We talk ourselves into the idea that being rejected is the worst thing that could happen and I promise its not. It can hurt a lot but any door that closes is a message that another door is open. There is no telling what this woman will do and I’m sure you’ve already run the scenarios in your head. Will she embrace the idea of getting to know you as a potential lover? Or will she say its not possible?

One big dating trap women get into is thinking that because they love a woman she must feel the same way. I’m sorry to say that often that isn’t the case. And its a trap because its a relationship that won’t ever be or won’t ever work out.

Instead of being afraid, embrace the idea that either answer will allow you to move forward in life. Waiting for 3 years while you are crushing on someone is like standing still while life passes you by. It’s time for you to live more fully and completely. I’m sending you love and hugs. Good luck, Mary


jay October 12, 2013 at 10:12 AM

Hi I read your page and I like it. Getting to the point im 25 yrs old and a late bloomer. I’ve like females sense high school, but was pick on and later in life only men dated me. I could never tell if a women is straight or gay, so when I tried to ask a her out she tell me she straight, bi but got a lover, or gay but in a long-term relationship. Sucks right so I stop and continue to date witch never works out. I decided this year will be my year to come out fully bout being gay. Im a dyke sense Im dnt a girly girl. It’s hard cause no one knows i like women and I have to lie to fit in to make a few gay friends. im scared that they will find out about me. I’ve never dated females what do I do?! Love, sex I dnt no im stuck I want to come out so can be happy if have any advice I will be glad to hear it. Thanks


Mary November 23, 2013 at 4:13 PM

Hi Jay,
I don’t know where you live, but check for local LGBT organizations. Attend a few events they have, you’ll meet other gay/dyke women for sure. Also google for LGBT meetups in your city or area. Another great way to start coming out and not feel so alone. And finally, being happy is about accepting yourself – everything about yourself and loving who you are. I encourage you to start learning how to do that too. A person who is happy in themselves makes the best partner and lover.

And also, check out online dating sites like which is free. You’ll see women your age and in your area who want to date. That makes the process that much simpler!

Good luck Jay, xo, Mary


jay October 12, 2013 at 10:25 AM

Hi I read your page and I like it. Getting to the point im 25 yrs old and a late bloomer. I’ve like females sense high school, but was pick on and later in life only men dated me. I could never tell if a women is straight or gay, so when I tried to ask a her out she tell me she straight, bi but got a lover, or gay but in a long-term relationship. Sucks right so I stop and continue to date men witch never works out. I decided this year will be my year to come out fully bout being gay. Im a dyke sense Im dnt a girly girl. It’s hard cause no one knows i like women and I have to lie to fit in to make a few gay friends. im scared that they will find out about me. I’ve never dated females what
do I do?! Love, sex I dnt no im stuck I want to come out so i can be happy. So if you have any advice I’ll be glad to hear it thanks.

any advice I will be glad to hear it. Thanks


Poutine November 20, 2013 at 3:16 PM

I’m interested in a woman at our local gift shop. She has been married a long time ago, but divorced as she (like says) prefers being free and her own boss. Asking her if she had a boyfriend (answer no) or girlfriend (answer no), she says it all could happen at any time. Well, she doesn’t reject it, but for me it’s not clear if she’s a lesbian. However, as she’s very independant and not looking for a relationship I’m wondering how I can ‘wake her up’ and let her know that there is someone in front of her liking her. I’m no butch at all, neither is she, so if she’s gay she maybe wouldn’t expect me to be one as well. So, I’m kinda affraid I (or we) miss our chances! And cause there are already so little around, I have to go for this one, because who knows what it will turn out to be. Is it weird to ask her out for a drink, even if she had TOTALLY NO interest in women at all? Please, girls, let me hear from you! Hugs and kisses!!


Poutine November 20, 2013 at 3:27 PM

As Mary asked what scares us I would say, in my case, I couldn’t shop at that gift shop anymore, as I would be stupid to maybe have thought she would been a lesbian, she could find it disgusting and tell her collegeas / friends (who some of them now me) that will find me desperate. Well, I don’t know you know; I find it scary because I never asked any woman out because in mostly they are straight or married.
Well, hugs and love once again, hope to get some response although I think I do know the answer anyway ;-)


Lipstick fem November 21, 2013 at 4:20 PM

Hi Mary thank you this is so inspirational to me…I’m only 25 and have never been with a woman before but I have been attractive to girls my whole life my first sexual encounter was with a girl that I friends know..I have not fully “came out” to the world lol but the important people in my life are aware..what scares me about asking another grl out is rejection..with men it’s not a issue because I always get hit on almost everyday..with women I don’t know if they look at me as not one of them because of how I look or act or dress i don’t know:( it’s like they don’t even look my way half the’s so frustrating when I tell sum1 that I’m into girls it’s like they don’t believe me lol.. But to sum it all up I have a huge crush on my friend who is a lesbian before I came out it’s like she already knew and knew that I had a crush on that I’m trying to be more open with it it’s like things between us has gotten weird..we still talk and text and kick it at work but she refuses to go anywhere with me 1 on 1 idk what 2 do are these signs that she is not in2 me?


Mary November 23, 2013 at 4:00 PM

Hi Lipstick Fem,
What you’re getting is the sign that she’s not available for you. This isn’t unusual. Many lesbians do not want to get involved with women who are just coming out or who seem to be “testing the lesbian lifestyle” out. I can’t tell you if she’s interested or not, but she’s clearly telling you by her actions that she’s not available. So enjoy the friendship you’ve developed at work with her and go out and find a woman who is available and interested in you. Good luck. xo, Mary


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