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How to turn a casual business friendship into something more.

#1
I have a coworker (she works at the desk across from me, but works for a different company and we do different things at the office) that I like a lot. She is beautiful and kind and easy to talk to. We occasionally talk when we are at desks, say good morning to each other, stuff like that. We ran into each other today in the cafeteria and asked me how I was doing, how was my day, etc. She told me something like, do you have any friends in Birmingham? I said no, because I recently moved and I work a lot. She said, "I'll give you my phone number and we can do something on the weekend if you want". Of course I took it and I now am not sure what to do. I want to do something with her, but I also want to turn this into something greater.

So here are my questions:
1. Do you think the only reason she gave me her phone number is because she feels sorry for me or do you think she is really interested in me? Do you think she is very interested in me because she gave me her phone number?

2. Should I get to it right away and try to set some activity up with her this weekend to get things going or should I give it a week or so? She mentioned that she likes to go to a rock climbing gym, and I would be interested in that.

3. How do I turn this into a more serious relationship? Should I just ask her out for dinner? Or should I try something else?

Please provide advice on what I should do from here. I want to ask her out before July 4th (the factory is shutting down and we have to move to a different area and I won't be able to see her every morning. I can see her, it just will be a lot more difficult). I am also an intern just for the summer and I live in Atlanta for school (she is also an intern, but I think she will stay there beyond the summer). I would like to keep the relationship going if I can.


Please help! Thanks in advance!

Re: How to turn a casual business friendship into something more.

#2
I think that she probably likes you and doesn't want to ask you out because it would be too forward, so she approached you because you're new in town -- which is safe for her. That said, this is a great opportunity for you to leverage this weekend into a date. Seize the day! If she likes you, she'll love that you pick up on her cue -- and that you take the lead and turn this weekend get together into more, and run with it. So, definitely contact her right away to set up something for the weekend, taking the lead so that this doesn't become a friend zone situation. Arrange a rock climbing date and show up with flowers or a simple sunflower or a rose for her, and bring a picnic so that you can go for a walk and have a nice, romantic meal on the grass afterwards. If things go well, hold her hand, and invite kiss her. Invite her to see a movie or do something else after the rock climbing date. And then build to a dinner date. It's great that she gave you this lead, and now you have to work it and build from a work relationship into a romance. ;) Hope that helps. Let me know if you have any more questions.
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.

Re: How to turn a casual business friendship into something more.

#3
Hi April, well it turns out she suggested going out to a concert yesterday, which she canceled somewhat at the last minute because she had to go into work early, and so did I. I have attached the pictures of the texts I have sent her, so please make sure to check them out. Here are my questions:

1. For some reason she has not responded to my texts today and I need to know whether it would be okay for me to call her tonight, or is that too desperate? Should I wait until tomorrow to make any contact? I keep checking my phone for her to respond but I don't want to lose her so I haven't sent anything since 12:00 PM central. What should I do? Is there a general principle I should follow?

2. I have questions about a date. When we go out to an event, you suggested to bring flowers. You don't think bringing a whole bouquet of flowers or roses is too much in front of a bunch of people?

3. And how do I know (and how did you know) that she likes me? How do I know if i can kiss her or hold her hand, and whether that's okay and not too weird?

4. Is it okay to ask her out to dinner over text or should it be in person or on the phone? What is the best way to ask her out? Should I ask her out to someone more general like rock climbing or something else? Is dinner too forward at this point?


April, I could not attach each picture individually so I have emailed them to you. Please review them before responding!

Re: How to turn a casual business friendship into something more.

#4
1. If you texted her today and she didn't respond, it's because she's busy. It's completely normal to respond a day later. I'm not sure what you texted her, but since you don't have a date set for this weekend, it's perfectly normal for her to respond tomorrow or even Monday. I think you should wait until Monday to see if she responds.

2. I think it's really nice if you bring her flowers. I'm not sure what you mean by it being "too much". It's not a flash mob! And it can be a single rose or a single sunflower -- it's just a nice way to date someone and let them know you think they're special. Bringing flowers, candy, a book -- something that sets the tone for the date is nice.

3. If a woman likes you, she'll say yes to a date! :) She'll laugh at your jokes. She'll compliment you. She'll flirt with you. She'll smile at you a lot. If she does any or all of these things, it means she likes you. Ask her out on a date, and if she says yes, bring her flowers, and if the date seems to go well, hold her hand and kiss her. Tune in to her feelings and the dynamic on the date to "take the temperature" of the relationship. If things are warming up, reach for her hand, or walk with your arm around her back or shoulders. Affection is a way to show you like someone. Use it! ;)

4. Asking her out on a date by text isn't as personal, special or as meaningful as asking her on a date by phone or in person. I think you should do it on the phone or in person -- not by text. Whether it's rock climbing, dinner, going to a concert, the zoo or for a walk on the beach -- just as long as it's something special that you think she'll like, it's okay. Choose a date that you think is going to make her feel good about you, dating you, and herself when she's with you. :)
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.

Re: How to turn a casual business friendship into something more.

#5
Hi April, in this post, I have questions about messages I sent her & the date. Please review the messages attached as a zip file.

Texts
1.So on Fri, Sat, Sun, I sent 5 texts. Yesterday, she told me that "she got all my text messages" & she went camping over the weekend and didn't have coverage. She seemed pretty nice about it, but I felt bad b/c I think it made me appear desperate.
a. How do I recover? Am I freaking out, but in reality it is no big deal, move on?
b. I read that I shouldn't make myself too available because it is a big turn off. I am thinking of giving it a two day or so break (Today (tues.) and wed.), and then ask her out on Thurs. or Fri. for Sat. night. Do you think this is a good idea to break from the mistake and see what I can do?

Date
1.Do you think it's too strong to go right to a date like dinner or concert instead of an activity like the canceled concert at the park?
2.I am having a hard time choosing the date. Idk what kind of music she likes or food, so Idk what restaurant to select or a concert that she would like, but the concert last week was mostly classical but casual atmosphere.
a. You said last time I need to choose a date that makes her feel good about me. How do I know what spot will do this?
3.How do I know if she would be interested in going on a date or taking this further?

4.The only time that we see each other is for lunch like 2-3 minutes, & that is if I make it at the time she is walking there, as I would have to speak to her alone. If I can't ask her out in person, how should I call her? What time should I call? What if she doesn't pick up? Should I leave a voicemail or no? How should I ask her on the phone if I must?

5.Is it ok to ask her what places she likes or suggests because I am new to Birmingham?
a. Or must I find the place before I call her or speak to her?

6.Do you think age is a factoring? She is 23 and I am 21. Do you believe she thinks, I am younger & she only thinks of me as a friend or is she really attracted to me because she straight out gave me her phone number? Or is age irrelevant? Should it not matter because I am the guy & I have the take the lead here?

Re: How to turn a casual business friendship into something more.

#6
I think that sending her five texts in a row over the course of three days -- with no responses from her in between -- isn't a good idea. It makes you look a little needy. :? I agree with what you wrote about giving yourself a break from texting -- but I think you should give it a week. The five texts in a row was kind of overkill. Wait until next week to contact her again. ;) And chill on the texting. ;) For future, if you don't hear from her after one or two texts, stop texting. To recover.... be cool and flirt with her when you see her. Gauge her reaction. If you get a chance, ask her out on a date in person -- which is the best way for you to see how she feels about you and your invitation because you'll see her body language, etc. If you don't get the chance to ask her out in person, pick up the phone and call her. If you don't reach her and get a machine, leave a message -- without the date invitation. Just tell her it's you and you'd love to talk to her. When she calls you back, you can ask her out. If she doesn't, when you see her you can gauge where you stand.

Bottom line: You're overthinking the date. Just pick a nice restaurant that's got good food, good service and has a nice vibe. If you want, you can ask her if she likes Italian food because you thought that might be nice. Also, from what you've said about her -- the rock climbing and the weekend camping -- it sounds like she's sporty, so maybe choose an active date, like playing tennis, going hiking with a picnic or going to the beach, or something that's outdoorsy. The bottom line is that if she says yes to a date, it's not going to be because of the cute restaurant you picked or the cool rock climbing place. It'll be because she's interested in you. So, don't sweat the venue too much. And don't worry about your two year age gap -- it definitely doesn't matter. Try to relax a little more, and have fun with it. If she says yes, then you should go and have a good time -- and if she says no, then you should move on.
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.

Re: How to turn a casual business friendship into something more.

#7
Okay, so here are my followup questions:

1.Are you saying that I should wait until next week to ask her out? If you are not saying to wait until next week, would it be ok if I ask her out this weekend if I can see her in person and ask her? If you are not suggesting to ask her out this weekend, would it be okay if I texted her to ask if she wanted to do something this weekend (not like a date) or do I still have to wait a week for that?

2. I also don't think you answered my question about the selection of the date. Do I actually have to select the date location and tell her about it when I ask her out or can I like present two options like hiking and a picnic or dinner and a movie?

3. How do I word it like it's a date? Like, if I were asking her out to dinner, I think she would know it's a date. But if I ask her if she wanted to go to Red Mountain Park this weekend for a hike and picnic, she might think it is something we are doing as friends and not as a date. How should I word it so she knows it's a date?

4. Do you have any ideas for a picnic? I have never done one of those before and I am not sure what to cook or include.

Re: How to turn a casual business friendship into something more.

#8
Yes! I suggested you wait until next week to ask her out on a date since you texted her so much this past weekend. Give her a chance to miss you. 8-) Besides, it'll give you a chance to chill out and regroup. As for the selection of the date, dinner is always a go-to date. It's a default because everyone eats dinner, and it's a nice, romantic way to get to know her as more than a friend. But since she sounds like a sporty person -- you had mentioned her rock climbing in a prior post and then in the last one, she'd been camping for the weekend -- I thought a sport date might be nice. That's why I wrote about inviting her to play tennis, go to the beach or go for a hike and a picnic. In general, it's nice when the guy plans the date, but there's no hard and fast rule, so if you want to invite her to dinner -- unless, of course she'd rather play tennis or go hiking -- that's fine, too. ;) Your third question is a very good one. :D You want to get out of the friend zone, so make sure you're flirting with her leading up to the date invitation, and then tell her that you'd really like to take her out on a date. Or you can say, "Would you go out on a date with me?" Be direct -- as long as you've been flirting with her leading up to the ask. The flirting is really important because it distinguishes you from a friend. Friends don't flirt. Guys who like her, and want to date her, do. That's her cue that your'e interested in dating, not friendship. 8-) As for a picnic, get a blanket, a bottle of wine and some chilled water, sandwiches, fruit and cheese, and some cookies. You can pull it together yourself, buy it at the market or a deli or bakery, and put it in a nice backpack or a cooler in your car. Choose a nice place with shade and grass and maybe a lake, and bring sunscreen and napkins and you're set!! :)
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.

Re: How to turn a casual business friendship into something more.

#9
Hi again, I wanted to ask a followup to the previous question. You mentioned to flirt with her leading up to the date. My problem is that I don't see her very much. When I come back for lunch, she has already gone to the cafeteria to get something and she comes back to eat at her desk. (she only gave me her phone number at a short conversation at the ice/water machine). So I don't think I have much time to flirt with her during the day, and when I come back from the factory work, it is usually at or past 5. So I miss her at the end of the day. Are you sure I shouldn't see if she is available this weekend for an activity to get some time to flirt with her then, and then move to the date next week? I am worried that I don't have enough time to flirt with her during the week at work. And by the way, how should I flirt with her? How do I do that?

What about just taking a shot for an activity this weekend and seeing what happens from that response and going from there?

Re: How to turn a casual business friendship into something more.

#10
I can tell you're chomping at the bit to get to her! ;) I think you have to balance the fact that you sent her 5 texts on Friday, Saturday and Sunday -- without a response from her until Monday, with wanting to get her attention. Too much too soon makes you look needy, and by waiting a week, you're playing it cool. 8-) So, if you can chill, do so. You had asked me in a prior post how you can recover from sending all those texts at once -- well, this is how you do damage control. Be cool. ;)

As for flirting, you should flirt with her whenever you see her -- and even when you don't! Flirting means complimenting her, teasing her, making her feel good about herself -- and you can do it with your words, your body language, your sense of humor -- and you can even do it by doing nice things for her. For instance, you can leave flowers at her desk, bring her a coffee or leave it for her in the morning,, put a nice card on her car windshield -- just do thoughtful things for her as little surprises. Basically, you want her to find you attractive, and get excited about the attention you're paying her. And flirting defines your feelings and the relationship so she doesn't see you as a friend -- because you're not acting like a friend.

As for taking a shot at this weekend -- I have a feeling you're going to do that no matter what. But if you can get yourself to chill out, not appear to be needy and set up the strategy to flirt and then ask her out next week... that would be better. Hope that helps!
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.