[Radpivo]

I helped hire an employee just under 2 years ago. She is 29 and I am 39. From the beginning I knew I was very attracted to her personality and demeanor(she was my type). We interacted a lot. We got on well, we had a bit of a teasing relationship, and spent significant time in the car together on calls. She sometimes would say we should do this or that in a real friendly way, but I always kept my distance due to the small office and that I was one of her bosses. We shared a lot of the same views, and I know she enjoyed talking to me on a range of subjects, and we shared the same political/social views. I know she has a boyfriend that she actually lives with, but know from our conversations that she probably doesn’t does share his life view, nor is her view particularly respected, and that he is not interested in more than macho male past times. In the past several weeks I know she has debated moving out – I heard through the grapevine. Just this past summer we had a company retreat and we were a bit flirty – at dinner she touched my thigh, she made sure we held hands on the beach at night after we had a splash fight, and apparently there were bets that we’d hook-up. In any event, she recently had to leave our small company as she needed to get a job closer to home. On the last day as she was leaving in the parking lot as I was saying good bye, I said that now she wasn’t an employee that it would be great to see here socially for a museum or just coffee to talk and she was very happy to hear that, but then I said “you see, I find you very intelligent and very interesting”(words that I had used to describe a day earlier as to the type of person I’m looking for), and she mid sentence, “Stop talking, you’re going to make me cry”, and we just stood there for a minute locked in gaze without saying anything as I didn’t want to to cry. I stared at her and said “well . . .” and turned and then she got into her car and I walked back to the office. Not sure what to do now. I’ve met 4 women in my life that had the right combination of qualities but for timing or work reasons I never acted, but I am certain she could be the one. Not sure how to proceed – call her up, ask her for coffee – I don’t want to her to slip away. At the same time I know there is an age gap, and I feel quite silly about this long crush, maybe that is all it is, but it doesn’t feel like it.

[April Masini, your AskApril]

Ask her out on a date!

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[Radpivo]

In April had a a good lunch and towards the end I expressed I’d like to see her socially in the next several weekends. the following Saturday I texted her about planning to meetup in the next several weeks and she didn’t respond for about a week. When she’s responded she apologized and said she had been really busy that weekend helping family member move and only just catching up with things, but didn’t respond to my query about meeting up. I figured it was an indirect way of saying no thanks. I texted her back but didn’t try to plan another meetup, and haven’t been in touch with her for 2 months. Couple weeks ago I catch her viewing my social media page and I view her back 6 six days later. Yesterday she texts me how my sum,dr is going, I send a brief reply, and she responds to a pick I send her of an event I was at, says her summer has been busy with family stuff, and says “We should get together soon because I miss our comversations”(we talked a lot while we were at work on business trips). Does this mean she might like me?

[April Masini, your AskApril]

Yes! 🙂

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[Radpivo]

After exchanging another text kidding about work, and getting a 2 paragraph detailed reply after a day or so, I suggested we “catch up” over drinks the following this coming Thursday – no reply yet. Figure she’s not going to reply. I just don’t understand, why she contacts me after a month and a half, suggests she wants to get together soon, and then not respond? I guess she was feeling lonely that weekend she texted me and doesn’t yet have a boyfriend to comfort her so . . . . Not sure if Thursday drinks was too aggressive. . . though she could suggest an alternative, possibly less charged day/time? Anyway, I think it’s best to just write her off as this delay/ non-reply probably shows she probably doesn’t have have much interest – yes?

[April Masini, your AskApril]

You can write her off…. or you can look at your own behavior and decide if there’s anything you’d do differently. 😉 For instance, when I suggested you ask her out on a date, you invited her to “catch up”. 😕 That’s not exactly romantic or letting her know you’re interested. 😉 If you want to date her, then my advice is that you act like it, so she knows what’s going on — not pull your punches, then wonder what could have been. 😳 You said that you had a “good lunch” with her in April and then you “expressed that you’d like to see her socially….” 😕 Things might have been different if you’d showed her that you were interested in dating her. You seem to be distancing yourself from romance with her…. and then deciding it wasn’t meant to be. I think you’d feel a lot more sure of things — whether or not they work out — if you actually ask her on a real date, so there is no mistaking your intentions, and pull out all the stops. It sounds like you’re fearful of rejection and that’s what’s holding you back. It’s understandable that you don’t want to be rejected — nobody does — but unless you give it your A game, you’ll always wonder if she really rejected you, or “things weren’t meant to be” which is a kind of wishy washy way of negating responsibility for the relationship and the date! Nobody ever died of rejection, and if that’s the worst thing you have at stake, I think that in future, you should be bolder and more forward about romance and trying to get the girl you want. 😉

You should buy and read [b]Date Out of Your League[/b], a book I wrote for men who want to win the dating game. You’ll find a lot of advice in the book that will be helpful. Here’s the link where you can get it: [url]https://www.barnesandnoble.com/w/date-out-of-your-league-april-masini/1016394885?ean=9780974676302&itm=1&usri=9780974676302[/url].

I hope that helps. Let me know how things go.

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[Radpivo]

Well I asked her to meetup for drinks, she never responded, then the day after the day I asked her out, she texted me that she was sorry but was waiting to get confirmation on plans with family(presumably for Thursday) and then forgot to text me back that she couldn’t make it. I don’t think she forgot, or if she is, it means she isn’t that interested. In any event she suggested we meetup one of the next 2 weekends a she plans to visit to a sick friend in my area(she’s about an hour from my location- So u know I suggested a place for drinks halfway between us). Not sure if I really should meet up with her as it may be a lost cause . . . Thinking if I do say, suggest not this week but the following and she reacts(I’ll tell if she is willing push off her visit). . . I can set the terms . . . Saturday, late afternoon, so that it’s clear I’m asking for a date(maybe museum followed by drinks? or a visit to winery/wineries . . .)

[April Masini, your AskApril]

I think you’re right — that she’s just not all that interested in dating you. 😕 But…. I think your plan is a good one. The only thing I’d add is that you continue to play the field and date other women so you don’t feel that all your eggs are in one basket. It also takes any edge of “desperation” off of the relationship you have with her now. 😉

Let me know how things go!

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[Radpivo]

Well, after I texted her that I couldn’t make the weekend prior, she did put her visit off 2 weeks ago, and texted me that she tried to arrange to come up to see the sick friend last weekend but couldn’t(she didn’t realize he was in the hospital) and just texted me today that she’s going to try to arrange to come up this weekend to see him in the hospital, and she’d like to meet me for “coffee or a cocktail to catch up.” Not sure, should I just let her try to arrange something, and then plan around her scheduled meeting time or say, well “come in the later afternoon and let’s catch up for cocktails afterward”. Coffee would definitely put me in the dreaded “Friend Zone”(if I’m not already there) and a cocktail would provide the proper environment to see her full intentions/openess, but at the same time I’m sort of uncomfortable on forcing the timing(he’s really sick . . .) so I’m not sure if he’s even well in the late afternoon so don’t want to come across as pushy . . . ideally though I should say, “let’s plan on cocktails around 5pm if that works per his condition . . . or something like that . . .” Or maybe I should say, “why don’t you just visit him this weekend so you focus, and let’s meet up during the week or another time” . . . or that “I’d prefer to see you without all the gloom . . .” I really don’t want to invest time to become her “Friend”

[April Masini, your AskApril]

You have to take charge and turn this into a date. 😉 Your instincts are good — wanting to veer away from coffee as a friend towards cocktails as a date. 😎 Stick with that line of thinking. Don’t cancel — instead, tell her you’d love to take her for drinks at 7 if that works for her. 🙂 Or if you want to make it a real date, tell her you’d love to take her to dinner at 7. Dinner is a commitment that drinks aren’t. 😉 Tell her there’s a nice place — and pick one out ahead of time — that you’d love to take her to. Offer to pick her up at the hospital so she doesn’t have to drive, or if she prefers, she can meet you there.

Let me know how that works out for you. 😀

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[Radpivo]

Well, the guy actually died, and I ended up seeing her at the memorial ceremony. We talked almost exclusively to each other, and were some of the last people there. I should have tried to setup a get together at the end, but didn’t feel comfortable doing so at a funeral, and just when we said good bye that I’d like to see her at a less somber occasion. My one colleague said she wouldn’t spend that much time with me if she wasn’t interested, so then I took a long shot called her up in later to setup a date, but she never got back to me.

In any event, I pretty much wrote her off after that, got rid of her number, etc., because I assumed she wasn’t into me, and really wanted not to think about it anymore. Quite honestly, I was done. Just last week we were going to be going to the same business event and she texted to me to check if I were going . . . at the last minute I couldn’t make the event and texted her, she said it was a shame and she would have like to have seen me. . . Anyway, this Sunday she texts me in the morning with “Good Morning!” and shares a link of an interesting article she thought I’d like, and then says “Have a great Sunday!” Does she want me to respond? For me to chase to stroke her ego- at least subconsiously? That’s what I’m assuming – correct? My plan is not to respond unless she reaches out again. Sound right??

[April Masini, your AskApril]

You have to ask her out on a date. Not a get together. A date. With a “d”. You have to say, “Would you like to go out on a date with me? I’d love to take you to dinner.” You’re making all sorts of excuses for avoiding rejection, and it’s turning into an enormous amount of energy spent without any return on the investment. 🙁 Until you ask her out, you’ll never know if she’s going to say yes! If she does, you’ve got a great opportunity to take things to the next level. If she says no, that’s a gift because you can stop wasting your energy on someone who’s not interested.

Time to step up to the plate! 😀

[Natalie Noah]

You’ve been oscillating between hoping she’s interested and protecting yourself from getting hurt totally understandable, and exhausting. From what you described she’s sending small, warm signals (reaching out after a long gap, sharing an article, saying she missed your conversations) but also giving you lots of wiggle room to interpret them. That mixed messaging can mean genuine interest plus life noise, or it can mean friendliness without romantic follow-through. Either way, it’s draining to live in the “maybe” zone.

Given that, the clearest move is also the simplest one, ask her out on a proper date not “catch up” or “coffee” unless you actually want just-friends coffee. Say something like, “I’d really like to take you to dinner Friday at 7 I know a place I think you’ll like. Would you be up for that?” Be specific (day, time, place). That removes ambiguity, signals your intention, and forces a concrete yes/no instead of weeks of slow burns and unread replies.

If she accepts, great show up with energy, curiosity, and a plan that makes the evening feel different from a work-colleague hangout. If she hesitates or keeps deferring without offering an alternative, treat that as information: she’s not prioritizing this. Don’t punish or lecture her just protect your time and ego by stepping back rather than chasing. People who are interested make time; people who aren’t make excuses.

Also be gentle about the memorial context: you were right to avoid a heavy ask at a somber event, and you did well to express interest afterward. But don’t let good manners become a permanent excuse for inaction. You can be considerate and still be direct about what you want.

Emotionally, decide what you’ll tolerate. Give one clear, confident invitation; if it’s passed over, move on and play the field. You’ll feel better knowing you tried without having wasted months wondering what might’ve been.

[Aida Omar]

Brother, at the age of 39, doesn’t suit shying away. Girls don’t like boys who are shy and very innocent.
I think the girl is using you for validation. When she gets tired of boring boyfriends, she taxes you.
AskApril was right that you should take her on a date, so that your confusion is over.
Plan drinks or dinner to get out of the friend zone, not coffee. If she says no, at least you won’t be wasting your time.

[Member]

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