5 Questions Men Should Ask BEFORE Approaching Women

August 24, 2015
Questions Men Should Ask Women

A few weeks ago I was asked a very simple question, how ‘should’ a man approach a woman. While it seemed quite innocuous, I soon became overwhelmed by the weight and depth of those few words. Overwhelmed because as I tried to craft a simple wish list of what most women would want, I realized how much context plays a role in a first meeting. That context can’t be easily listed in a few steps and tied with a bow. Several factors influence how the first interaction should/could go – location (church, grocery store, or office holiday party?), connections (do they have mutual friends?), personal mood (is she too busy to be bothered?), etc.  There isn’t one way for a man to approach a woman because context matters. However, there is one consistent truth regardless of location, attitude, connections, and attire. A man should be prepared. So instead of telling men what to say or do after approaching a woman, here are 5 important questions men should ask and answer for themselves before venturing over for that first hello.

1. Are you truly ready? Too many people enter into new romantic entanglements before they’ve properly disconnected from their last one. Detaching properly means both emotionally and physically as not doing so leads to confusion, complications, and trust issues long before any possibility of happily ever after. If you are ready, you’ve taken time to evaluate past mistakes and learned the meaningful lessons. You don’t have inappropriate interactions with your ex that could complicate the life you’re hoping to build with someone new. If everything is still your ex’s fault, you aren’t aware of at least a few of your shortcomings or you’re still in a “situation” with someone from your past, you aren’t ready. Why bring someone into your life during a time when you aren’t operating at your best? Avoiding a few moments of introspection could damage a lifetime of possibilities.

2.  What’s your objective? Because you never know what that first hello will evolve into, be intentional from the start!  Do you know exactly what you want? If you’re merely seeking a new laymate, be honest with yourself and do us all a favor and be honest with her. Too many relationship-like activities are occurring without the people involved understanding their ideal outcome. Are you hoping to meet your future wife and mother of your kids? Would you prefer a casual companion for a few dinner and movie dates? Regardless, until you have a CLEAR idea of what you want/need at this point in your life, you’ll have difficulty acquiring it. Objectives not only determine why you date but how you date.

3. What are you offering? After understanding what you aim to get, take time to think about what you’re able and willing to give. Women want time, trust, honesty, passion and everything in between. If she’s financially stable and yearning to get married, maybe you shouldn’t approach her if you’re unemployed and striving to be a playmate. You should enhance her life, not cripple it. As amazing as you might think you are, take time to really consider if the woman you want should want you. Are you able to provide more than promises and excuses because she’s likely been offered plenty of those by men now in her rearview.

4. Is now the right time for her? You may have the best intentions and be in a great emotional space, but she’s simply not interested in being approached at the moment. Maybe she lost a loved one or went through a bad breakup. Maybe she’s focused on final exams or a major project at work. Maybe she’s just frustrated with the dating scene and is comfortable with the invisible “I’m-Not-Interested” stamp on her forehead. Guys, always take a few minutes to read the situation. A woman is less likely to entertain a new suitor if she’s in certain moods/mindsets. Just because the moment is perfect to you, doesn’t mean it’s right for her. Not making a move may be the best move of all.

5. Are you prepared for a No? If you cannot handle her possibly rejecting your advances, rethink the situation. Being equally comfortable accepting a yes or no equates to maturity and confidence. I’ve witnessed guys get defensive, call the woman names or commit some other equally disrespectful act simply because she didn’t want to offer her phone number. Know yourself well enough to know if you can receive whatever she says without making a scene or becoming a nuisance. Note: ‘No’ does not mean try harder. Most times, no really does mean No. Get used to it, be comfortable with it, and don’t take it as a personal insult. Read more here: HOW TO LOSE A GIRL IN 10 WAYS

I’m sure this list isn’t exhaustive and could apply to both genders. What are your thoughts on this list and is there anything you’d add/revise?

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(originally posted August 2014)


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  • Reply Conrod Kelly August 22, 2014 at 6:19 PM

    “If she’s financially stable and yearning to get married, maybe you shouldn’t approach her if you’re unemployed and striving to be a playmate. You should enhance her life, not cripple it.”….WOWW!!!….not sure about this.

    So if a man can not offer monetary support he will cripple a financially stable woman? WOW!!!! Might she be interested in learning that he is unemployed because he is self-employed, or working on PhD, on in between jobs (he could have been an executive that was recently displaced), or trying to pursue their true passion and resign from the corporate grind?

    Is a financially stable woman looking for more stability or for someone that may bring what she is missing in her life (she appears to be financially stable on her own)?

    • Reply myndmatters August 23, 2014 at 7:02 AM

      Thanks for your comment! I appreciate you reading/supporting the site!

      I believe it unnecessary for women to apologize for wanting a man that can be financially stable. In general, I don’t find it a woman’s (person’s) responsibility or purpose in life to correct the misconception that we should accept any and every excuse someone presents as fact/evidence/rationale for why they aren’t suitable to be our life partner. If I don’t want it, I shouldn’t have to accept it nor justify to someone else.

      If a woman wants to get married and a man wants to simply “date” or be her “playmate,” they aren’t compatible and she should feel confident in walking away. What he’s presenting doesn’t better her life, it brings complication and complexity. (see: Playmate post)

      Focusing on the financial, I’m not referring to grad students, self-employed, executives with transferable skills that are clearly between jobs or any reasonable situation for why he doesn’t have a typical 9-to-5 or a lot of money in the bank. Most ‘financially stable’ women aren’t interested in a man that can’t buy a meal, has no long-term vision, and no money in the bank. It may be uncomfortable to say or accept but that’s crippling to her situation. I’ve dated a guy that wasn’t financially stable but I thought could enhance my life in other ways. I was wrong and when you know better, you do better. We should stop trying to make all situations and dynamics acceptable simply because the truth is hard to hear.

  • Reply Roshell August 16, 2014 at 1:02 AM

    Amen to #2. Great post with invaluable insight.

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  • Reply Sonia Thompson December 4, 2013 at 9:30 PM

    great post. I think #2 is a really big deal – people aren’t always forthcoming with their intentions, and that’s probably because many aren’t quite sure of what they are. The more honest we are with ourselves and others the better

    • Reply Renita Bryant, Author December 6, 2013 at 8:46 AM

      Great point Sonia! I had a male friend mention that recently. He believed #2 is difficult because intentions evolve and feelings shift. In my response to him, I acknowledged that truth but also reminded him that your objective at the beginning will always be your objective at the beginning. This is about where a person is at a given moment in time. Too many women fall for a guy hoping he’ll change his thinking along the way and often that doesn’t happen. Men have to stop selling the dream of “maybe” and women have to get clarity of where he is from the start (and respect/accept his position).

  • Reply Conrod K December 4, 2013 at 12:02 AM

    Great post. The one theme I picked up on was the need for both parties to be honest with themselves and each other. Too many first encounters start out with shades of the truth.

    I’ve always wondered how receptive a woman would be to the following: “Hi, I’m Malcolm. I came over to speak to you because i thought your were attractive and i wanted to get to know you better to see if we are compatible. If you are open to the idea, I’d love to get your name and your contact information (or give you mine)”….how would you respond?

    My reason for asking is that we (men) need more information to inform our intentions beyond wanting to get to know the pretty girl that caught our eye.

    • Reply Renita Bryant, Author December 6, 2013 at 8:48 AM

      So very true Conrod! Depending on the woman and whether or not she’s “open” to being approached at that time, Malcolm’s tactic would probably be well received. I don’t think there’s anything wrong with honesty and clarity.

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