[OAl]

Hi April,

I am a guy who is attracted to my female friend. We are both 23. I have known her for years and she is one of my closest friends. Last summer, we became closer to one another. We talked and saw each other more often, either with friends or alone. This is when I started to like her. I had a feeling that she liked me too, but wasn’t sure. Late summer, I knew I wanted to ask her out, but I didn’t know when I would. I finally did a couple of months later. It was too late as she had just started seeing someone. She told me that she liked me all along, but wasn’t brave enough to tell me about it. I may have come off a little hurt by the missed opportunity, but assured her that our friendship wouldn’t change. That was late October. Since then, everything between us has been normal. We talk regularly, and at school we see each other about twice a week. We have never talked about this since then.

In late February, she suggested that she was no longer seeing that guy. In mid-March, I confirmed it by directly asking her. They are still friends, but I don’t know how long it had been since they ended things. A few times since then, we’ve spent alone time together and cuddled (hugging and holding hands). Although cuddling with her is not something new, I tried to test to see if she’s interested. On a couple different occasions I kissed her on the cheek while cuddling. The first time was because she was having a really bad day. But the second time I did it was to see if she would kiss back. She pulled away after a couple kisses, but never said anything because I played it off well. When we’re together and talking at other times, there is usually physical touching.

As of late, we have not talked much. In late March, she said she was being overwhelmed by everything and decided to shut off her phone for a while. I’ve only spoken to her and seen her a couple times since then, because classes are now over as exams are underway. However, I know this will change next week once she is done with school. But this gap in communication has made me wonder if I am taking too long to act on this…again.

And now my questions: In your opinion, does it sound like I’m waiting too long to ask her out now that she is single? I want to ask her out again, but want to know how. Should I directly ask her, or test to see if she’s interested first? I’ve tried to make it obvious that I’m still interested with the affection that I show her, but does it seem obvious? I’ve heard some girls like persistence, so should I be persistent in asking her?

I don’t want to put myself out there if she’s not interested. Will this jeopardize what we have, make me look desperate, or annoy her? When I told her how I felt in October, she was talking about the future possibility of us and said something along the lines of, “if this ever comes up again, I’ll be the one to tell you”. Since she hasn’t said anything yet, do I take it that she’s not interested, or is it even still worth trying? I also asked how long I should wait to ask her again if she became single and she said something along the lines of “when I end something with a guy, I need time to get over it”. I think she’s past that period, but how do I make sure without making it too obvious that I am interested?

Her birthday is next week. I plan on giving her a thoughtful gift. Do you have any tips on how I should execute this in hopes of getting her interested again? If it helps, she is Taurus.

Your opinion is appreciated.

[April Masini, your AskApril]

You’ve put yourself in the friend zone for way too long. It’s time for you to get out, NOW! 😉 I’ll answer your questions, below, but bottom line: If you don’t ask her out on a date and either take her out and move the relationship to the next level, or accept a rejection and cut contact so you can find someone to date who wants to be with you, you’ll stay in this bad pattern. 😳

[quote]n your opinion, does it sound like I’m waiting too long to ask her out now that she is single? [/quote]

Yes.

[quote]Should I directly ask her, or test to see if she’s interested first? [/quote]

Yes, ask her out. I’m not sure why you would test anyone about dating…. 😕 Testing someone implies there’s a right and wrong answer.

[quote]I’ve tried to make it obvious that I’m still interested with the affection that I show her, but does it seem obvious?[/quote]

No. It’s not obvious at all, because you haven’t asked her out. You’re acting like a friend, not a guy who wants to date her.

[quote]I’ve heard some girls like persistence, so should I be persistent in asking her?[/quote]

Persistent? 😯 You haven’t asked her out once. You’ve given her the very clear idea that you’re just a friend. Before you start talking about being persistent, you have to get off the bench and get into the game. 😉

[quote]I don’t want to put myself out there if she’s not interested. Will this jeopardize what we have, make me look desperate, or annoy her? [/quote]

If you ask her out, you’ll look like a guy who’s interested. If you continue on the vector you’re on now, you’ll continue to look desperate. 😳 Keeping a woman around as a friend because you’re afraid of rejection isn’t attractive…. You have to man up and realize that she may want to date you or she may not want to date you, and that if she doesn’t, you need to move on.

[quote]When I told her how I felt in October, she was talking about the future possibility of us and said something along the lines of, “if this ever comes up again, I’ll be the one to tell you”. Since she hasn’t said anything yet, do I take it that she’s not interested, or is it even still worth trying?[/quote]

No, it is not worth your trying to tell her how you feel and then not following through…. 😳 This won’t ever work. If you like a woman and want to date her, you have to show her, not tell her. 😉

[quote] I also asked how long I should wait to ask her again if she became single and she said something along the lines of “when I end something with a guy, I need time to get over it”. I think she’s past that period, but how do I make sure without making it too obvious that I am interested? [/quote]

You don’t. Why on earth would you want to look like you’re not interested when you are? The answer is: you shouldn’t. Set your sights on what you want and go after it. 😉

[quote]Her birthday is next week. I plan on giving her a thoughtful gift. Do you have any tips on how I should execute this in hopes of getting her interested again?[/quote]

I think that you should cut to the chase and end this misery you’re in. Ask her out on a date for her birthday. Make it clear that it’s a date, and then give it your best shot! 😉

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[OAl]

Thank you for the response! Sorry about the double post. I didn’t realize I had done that.

Just to clarify, I did ask her out in October. So this would be my second time asking her out. The first time, she said no because she had just started seeing someone else. Otherwise, according to her, it probably would have been a yes because she liked me too, but was scared to tell me. I’ve been trying to show her that I am still interested, even though we haven’t talked about it since that time.

Since being single, she hasn’t brought it up. So does that mean she’s not interested, or that she’s waiting for me to ask her out again? That’s where the persistence question came from. Aside from the affection and regular communication (in-person and texting), she hasn’t shown the same kinds of signals that she did when she first liked me, which is why I’m unsure. I just want to make sure that the window of opportunity hasn’t passed because I took too long in asking her out the first time.

She is a very close friend, so I have to approach it a little differently to keep our friendship intact. As this will be my second time asking her out, I’m trying to save face, regardless of the outcome.

[April Masini, your AskApril]

Definitely ask her out. It sounds like she hasn’t brought up dating you because it’s not her place to do so. It’s the guy’s place to do the asking. 😉

As for the friendship, I hope I can set you straight: Men and women can’t be friends. The reason for this is because one person always feels differently than the other and this inequity creates miscommunication at best and hurt feelings at worst. In addition, you can’t really be honest with her when you like her romantically because you’re always going to be looking for an angle to date her. If she’s dating someone else, you can’t really be honest about your feelings about her boyfriend because YOU want to be her boyfriend, and if she asks you your opinion about the relationship she’s in with someone else, then you can’t really give her an honest answer because you’re going to be jockeying for position because you want to date her. 😕

Over and over I hear from men who are in the friend zone, like you are, because they want to be around a woman they like, rather than risk asking her out and hearing rejection, and losing her altogether. But the entire time they’re in the friend zone, they’re spending tons of energy trying to figure out how to get out of it — without getting out of it! 😮 My advice is to get out of the friend zone! You may be rejected — but you may not be, and if you don’t get out and give it your all, you’ll never know. 😉

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[OAl]

Her birthday is in the next couple days. I’m going to see her. I will give her a gift, and then ask her. I just want to be sure of something…the first time I asked her out, she said no because she just started seeing someone else. Otherwise, we might have been together. She also said “if this topic comes up again, I’ll be the one to bring it up”, referring to any future chance of us being together. Since she explicitly said this, do I treat as if she isn’t interested, or do you think she could be playing games and waiting on me to ask her? Keep in mind that we haven’t spoken about this since I first asked her out in the fall.

Please advise on my approach…I plan to ask her after I give her the gift. I am first going to ask if she’s seeing anyone, and if she’s not, I will ask to take her on a date. I will also tell her that there is nothing to talk about, but that I will show her instead. She has a tendency to analyze (and overanalyze) things, so I will have to convince her not to think about it too much and just try it out. Do you have any suggestions on how I can convince her to not think too much about it and try it out? She might be scared to try it out because of our friendship.

On the weekend, we will be going out to celebrate her birthday with our friends. So I’ll be seeing her for a second time this week.

[April Masini, your AskApril]

You’re making a lot of excuses and giving yourself a lot of reasons not to ask her out…. instead of just doing it 😳 I imagine you’re afraid of rejection so you’re postponing the possibility of that rejection — while at the same time, postponing the possibility that she’ll say yes. Either way, you’re going to be better off than you are now. If she says no, you can move on and stop expending energy on someone who’s not interested, and if she says yes, you can proceed and get to know her in a dating relationship! 😉

[quote]Please advise on my approach…I plan to ask her after I give her the gift. [/quote]

😯

I’ve already advised you to ask her out for her birthday. I can see you didn’t take that advice…. If you want to ask her out after giving her a birthday gift, that’s fine, too — but the main thing is to ask her out on a date! 😀 You’re going to feel a lot better once you do. Right now, you’re making yourself a little crazy spending so much time figuring out if you should, how you should, and when you should. If you read this string of questions and answers, you’ll know what to do. 😀 😀

[quote]I am first going to ask if she’s seeing anyone, and if she’s not, I will ask to take her on a date. [/quote]

I don’t think you should do this. 😳 I’ve already explained to you that dating is competitive, and you’re going to have to compete for her. Just ask her out. If you back down before you even try asking her out, you’ll lose the opportunity to win her over! 😉

[quote]I will also tell her that there is nothing to talk about, but that I will show her instead. [/quote]

I don’t think this is a good idea. Don’t TELL her there’s nothing to talk about — just don’t talk about whatever it is there’s nothing to talk about. If you tell her there’s nothing to talk about, you’ll come off as bossy. Just ask her out on a date! 😀

[quote]She has a tendency to analyze (and overanalyze) things, so I will have to convince her not to think about it too much and just try it out. Do you have any suggestions on how I can convince her to not think too much about it and try it out? She might be scared to try it out because of our friendship. [/quote]

Don’t try to convince her of anything. Just ask her out on a date. 😉 I know you think she’s overanalyzing things, but it looks like you’re the one who’s doing that.

I’m trying to help you, but I’m not sure it’s working here….so, I think you need to buy and read Date Out of Your League — a book I wrote for men who want to win with women. It’s got a lot of basics, as well as some more sophisticated tips and pieces of advice that are REALLY going to help you. The book is only $8.99 and you can get it here: [url]https://www.askapril.com/relationship-dating-advice/date-out-of-your-league.html[/url]. Please buy the book and read it!

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[OAl]

I appreciate your feedback. I am not usually this way when it comes to women. I’ve just been treating this differently because she is a close friend. But since your last reply, there have been a series of events that have transpired in the past week.

Due to a sudden circumstance, I was no longer able to attend her birthday party over the weekend. I used that as an opportunity to take her out on the day of her birthday. However, when I asked her, I did not tell her it was a date. But it didn’t matter because the night went well and she told me she had feelings for me. We shared a moment, but she told me she’s unsure of dating me for a few reasons:

1. Our friendship

2. She’s not sure if she’s ready to date because of her experience with the last guy she was seeing. She’s moved on, but said she needs to work out some personal issues.

3. Her busy schedule (school)

I tried to address these concerns of hers right then and there but was caught a little off guard by her revelation, so I couldn’t give her the most complete answers. She understood and we agreed that we would talk again to address these concerns to see what can come out of this. This was before the weekend. I had to leave town and didn’t come back until Monday night. We had a nice chat on the phone the night I got back, but didn’t talk about this because I thought we would address it in person and she had a final term paper to hand in on Tuesday. I thought I would see her Tuesday night but she wasn’t able to meet up for a reason I don’t know. She has had a few other things going on this week but she’s not as busy as she will be next week, when her summer courses start.

Is there anything you can suggest for me to mention when I address her concerns? I briefly did the night we went out, but we’re going to talk about this again so I want to be better prepared. I already have an idea of the things I’m going to say, but any insight you could provide would be great. She knows that I want this to work out, so it’s mostly in her hands at this point.

We’ve been texting regularly since this all happened, but she hasn’t said much about this. I know part of the reason is because initially I was out of town and she was finishing up her school work. But she’s been free since Tuesday night, so I’m curious to know if you think her silence on this subject means that she’s leaning one way or the other, or that she’s still thinking about it, or if it means something else. I am hoping to take her out this weekend, so that we can talk and move things forward.

Is there anything I should / can do right now to help the situation? Should I bring it up now (over the phone) or wait until we meet in person? When I text her, should I be flirty and suggestive? I haven’t been too flirty or suggestive since that night I was with her. But I have been saying some sweet things and complimenting her. I meant to tell you about this sooner but haven’t been able to.

[April Masini, your AskApril]

I’ve given you a lot of advice, but you haven’t taken it. 😳 It seems that you’re trying to avoid the problem here by talking about it instead of taking action. That won’t help. 😳 There’s an old saying about how you can lead a horse to water but you can’t make him drink. I think that applies here. 😕

The best I can do at this point, besides advise you to re-read what I’ve written here, is to urge you to please buy the book I’ve already suggested, Date Out of Your League, [url]https://www.askapril.com/relationship-dating-advice/date-out-of-your-league.html[/url]. Read it and use it! 🙂

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