[Freddy]

I have every reason to believe that this Woman likes me…over a two year period I saw her infrequently…she has always approached me to talk to me when we saw one another in a store that we had sometimes worked together in during the hour that I was there; getting her phone number was easy when I recently decided to ask her for it. We are both adults over 30.

We met out for happy hour once and went on one date. It took some persistence to make our face to face meetings a reality. I was not sure if we were going to go on our first date as she was not responding to me but came around the day of and showed up on time looking great with her hair done and in very nice clothes. I thought it was a good sign that she did her hair and did not just throw something on and leave the house.

In this period of time I have met her mother and am liked very much by her as I have been told. [Her best freinds in life are her sisters, thier boyfreinds and the mother.] This woman has always texted me back and she responded to me very well on our date. She never pulled away from me; I said something very sweet to her and got a look I will never forget.

After the date I texted her to say I had a good time and that she looked very beautiful that evening…she responded in a few minutes saying she also had a good time and thanked me for the movie.

However during the first date I discovered that she is still hurting from a recent marrage and still lives in the house they bought together. [She has been sleeping at the mothers house a lot] Since the date she has remained polite but texted me that the BBQ at her mothers house will be rescheduled for another day. For all I know she is still married, seperated or ?

I think that she is not ready for another guy yet and have decided to stop calling her or texting for a few weeks as my last response to her text regarding the rescheduling of the BBQ was – OK…I start work again this week from vacation and asked her to let me know what she is planning…I said I would be on her side of town in a week or so and if she wanted to grab a bite to eat at happy hour to let me know.

I feel that I did a great job with her, I feel that I am liked by her and her immeadiate family but unfortunately this seems like the wrong time to pursue her as she seems hurt and consumed with whatever is going on in her life right now.

It does not feel right to continue to be the pursuer if it is going to make her pull back. We had a nice time, she is not angry with me and I don’t want to burn any bridges. I think that if I stopped calling on her that it would not make her feel that I am uninterested because I believe that I showed much interest in her already and left the ball in her court with the last text.

I know this may result in nothing and I am prepaired to accept that but I am a man and am used to doing all of the pursuing. Is it wrong for me to hope that I left a good impression on this woman that I would be someone she thinks about in the future when she is no longer struggling with this situation in her life?

I wonder if a woman would call a guy after weeks or even months if they have only good memories of that person? Maybe she will…maybe she wont but again, I am a man and don’t know what women think in these regards. I do not think I did anything that would cause her to dislike me.

I really like this woman a lot and it’s hard for me to let it go but I feel it’s the right thing to do. My freind suggested that I call her in a few weeks, ask how she is doing and let her know that if she needs anything that she can call me.

[April Masini, your AskApril]

It sounds like you have some unanswered questions about this woman. Perhaps if you knew the answers to the questions about her prior (present?) marriage, you would know better how to proceed. My advice is that you give her a phone call. Ask her how she’s doing, and what’s going on. It doesn’t have to be a phone call in which you ask her out on a date. You can just call to say hello because you’re still interested in her.

It sounds like you got a little information on your first date about her marriage ending badly. You owe it to yourself to find out how long ago she separated and divorced. If it was just a few months ago, she may not be ready for intimacy and needs to be approached gently, but firmly. If she’s dwelling on a break up that happened over a year or so ago, she may have some more complex issues to work through before she’s any fun. And if she’s still married, but divorcing, I’d give her six months and then call her again and see if she’s in a different state of mind and more interested in going out with you then.

Then again, there’s always the possibility that you’re both being slightly tentative and misreading each other’s cues. That’s why I think a nice phone call one evening or weekend might be just the thing to guide you into the next step.

[Freddy]

Thank you for that advice. I was thinking about doing that but you really put in perspective for me.

[April Masini, your AskApril]

Let me know how things are going for you…. 😀

[Natalie Noah]

A careful balance between interest and patience, and I can see why it feels complicated. What stands out is that Freddy has been attentive, respectful, and considerate of her current emotional state, which is exactly the kind of approach that builds trust and shows genuine care. He has correctly noticed that she’s still processing a recent marriage and is mindful not to overwhelm her, which demonstrates emotional intelligence. His self-awareness about not being the pursuer at a time when she may not be ready is a strong point in his favor.

At the same time, the uncertainty of her circumstances is understandably challenging. Without clarity about her marital status or her emotional readiness, it’s difficult to know how to proceed without risking frustration or disappointment. Freddy’s instincts to step back and let her initiate some contact are wise, but the key is to maintain some gentle presence so she doesn’t feel abandoned. Checking in with a casual phone call, as suggested, is a subtle but effective way to keep the connection alive without pressuring her.

It’s also worth noting that her positive reception to him on the first date, along with the family approval, is meaningful. These are indicators that she values him, but life circumstances may be limiting her ability to respond fully. People often need space after a difficult relationship, and respect for that process can actually strengthen a future connection if it’s handled with patience and sensitivity.

The challenge for Freddy is maintaining the balance between patience and presence. It’s okay to hope that he made a positive impression, but he should also prepare for any outcome. Women in situations like this can reach out after weeks or months if they genuinely feel a connection, and often the right timing makes all the difference. His approach should be calm, supportive, and open, without creating pressure or expectations.

Finally, this is a moment to focus on steady, low-pressure engagement. A simple, warm check-in call or text that shows care but doesn’t demand a response can keep him in her thoughts without risking discomfort. If she’s ready to move forward, his patience and respect for her space will have left a strong, lasting impression. If not, he still walks away with dignity and self-respect, having managed the situation thoughtfully and kindly.

[Member]

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