A
female
age
36-40,
anonymous
writes:Hi everyone!While working a contract gig, I developed a huge crush on someone in our building. We chatted a little bit, kind of had lunch once, but our schedules were never consistent. On my last day, he left early. I planned to ask him out for drinks but I didn’t run into him all week. So, I decided to write him a note. In the note, I told him it was my last day and that I would love to meet up with him sometime for coffee and get to know him better. That is if he was interested. To my surprise, the following Monday, I received a text from him. He thanked me for the letter and said he would love to meet up. We chatted a little bit and I bid him goodnight. A few days passed and I reached out to him to casually invite him out to see a show and he responded and said that he would love to but he already had plans and that maybe we could do something next week. The problem was that I was planning on traveling after my contract ended and would be out of the country for a month. I told him maybe we could get together after I got back. and he said sure with a wink face. Well, now I’m back. I’ve been back for about a month, and I can’t decide whether I want to reach out or not. Not because I’m not interested but because I don’t want to embarrass myself. There’s a part of me that thinks that if he were excited/interested in meeting me up that he would have sent me a message by now, asking if I am back or not. And then there’s the other, obviously, just plain rational part of me that says, ok, you told him you’d contact him, you haven't done that and that’s why he hasn’t contacted you. Also, another part of me says it’s been almost two months… it’s too late. I don’t usually approach men, and so I feel like maybe I’m being a little forward and that if I contact him, it would be my third attempt at seeing this guy, and I don’t normally do that. The very last part of this, and I think it's part of the reason I feel so hesitant is that he’s a super successful, very worldly person and I am so intimidated by him. Questions for you!What would you do?Is he interested if he just “sure ;)”? Do you think it seems a little much when a person you don’t know too well reaches out three times?
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Fancy yourself as an agony aunt? Add your answer to this question! A
male
reader, N91  +, writes (17 June 2018):
 You took the plunge, it didn’t work out, you’ve seen it’s not the end of the world.
Hopefully this has given you more confidence for the future and has shown you that rejection isn’t all that bad!
Best of luck.
A
female
reader, Honeypie + ♥, writes (17 June 2018):
 Well, then you just check him of your "to do list or the I wish I had reached out list".
It's OK. Not all guy you meet will be interested to the same level as you. It happens, the things is to NOT waste time on the ones YOU have no interest in and who has none in you.
But reaching out and seeing what's up you can now move forward knowing that you DID try and he just was a no-go. Off to find someone who is better suited for you.
And thanks for the update!
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A
reader, anonymous, writes (17 June 2018): This is verified as being by the original poster of the questionHello everyone.
Thank you all so much for your insight and suggestions. I eventually reached out to him again. We chatted a little bit but it became very evident to me that he was not interested in seeing me.
That's totally ok, and I have since moved on!
Thanks again!
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A
male
reader, BE125 +, writes (1 June 2018):
Hi, I imagine a lot of people in a similar position feel like you do, so you’re not alone, that’s the first thing. The other thing that was enlightening for me is that you said you didn’t want to embarrass yourself by reaching out, if I understood you correctly. Do not be afraid of that! You will not be embarrassing yourself at all. As I guy, I would find it quite refreshing for a lady to initiate something. I admit that at times I get weary because I feel like I’m the one who always has to be the initiator! I think your guy friend is probably waiting on the other end of the phone for you. That’s the problem sometimes, two people sit on opposite ends of the phone waiting for the other to initiate, and when that happens nobody communicates. It’s an endless circle of silence. I recommend reaching out to him, I believe he will appreciate it!
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A
reader, anonymous, writes (29 May 2018): Why? Contact and communication lets me know you like me. I'd like that someone takes the time to leave me a lovely note inviting me for a drink. Then thought of me, and offered me an invitation to a show. A confident, pleasant, and interesting person.
He was receptive every-time. Three-time's a charm!
I say, go for it! Come on! What have you got to lose? How would you embarrass yourself? He's seems polite, receptive, and I do believe he's interested.
Don't dally, and miss your window of opportunity!
Call him!
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A
female
reader, Honeypie + ♥, writes (29 May 2018):
I agree with the JUST MESSAGE him and see what happens. Just ask him if he is still interested in meeting up for drinks and what day might work for him.
That way he has AMPLE way of showing interest or turning you down politely.
And if he does turn you down, well then you tried and can move on to asking someone else out.
If he DOES say yes, and give you a date to meet up, then go for it and see how it goes!
Sure, rejection isn't fun. But really you can either sit on your hand and speculate until the cows come home or you can jump in with both feet and see where it takes you.
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A
male
reader, N91 +, writes (29 May 2018):
Why would he need to contact you first?
You’re the one who went travelling so I’d say it’s more on you to let him know that you’re back. Why would you be embarrassed? Every time you’ve messaged him he’s replied positively.
He’s just as human as you are, what does his success have to do with anything? If you’re intimidated by him then how do you expect this to develop into anything serious?
The only thing I see as being ‘a little much’ here is how big of a deal you’re making this. Just messsge him and see what happens. What do you have to lose?
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