Summoning the metaphorical balls to make the first move

[amazingcuzitis]

I (26F) have been spending a lot of time with this guy (32M), and things seem to be going well. We were acquaintances until around May of last year, when we started hanging out regularly as friends. Right away I knew I was interested, and, you know how it goes, I spent months wondering if he liked me back. It seems to me that at this age, there’s really only one reason for two people of the opposite sex to start hanging out regularly (to find out if you’re interested and if you see it going somewhere). The thing is, we’ve both been single for a looooooong time, and we both know exactly why; because we’re incredibly shy.

 

Last month he asked me to be his +1 to his work’s Christmas party, and, despite our awkwardness, it was really fun and we had a great time talking and getting to know each other better. Afterwards, he walked me to my car and then invited me to a party he was having the next week. When I got there, we got away from the crowd and talked deep into the night and he brought up the topic of previous relationships, and we both shared our emotional scars and our hopes for the future.

 

So now here we are. It’s been a few weeks since the party, and Valentine’s Day is quickly approaching. I’ve come to the realization that if I wait for him to ask me out, I’ll be waiting forever... and I’m thinking of using V Day to my advantage. I figured that if I ask him to spend Valentine’s Day with me, he’ll figure out that I’m interested. If he doesn’t want to spend it with me, I’ll know right away that he’s not interested in me and I can stop wasting my time. But if he does want to go out, I’ll see what the general vibe is throughout the day, and if I think he still hasn’t figured out that it’s a date, I’ll nut up and tell him how I feel (at the end of the night, just in case it doesn’t go well haha). And, if the feeling isn’t mutual, we’re both adults and he’s a very kind man so I’m not worried about anything worse than a polite declination.

 

Thoughts? Encouragement? I have NEVER asked a man out before, but it’s something I think all women (even shy women) should do once in their lives. If you’ve ever tried to make the first move and it went well, I’d love to hear about it! I could really use some motivational words to help me get over my fear and nervousness!

[Wiseman2]

It may be best to simply invite him to come for dinner, or go for coffee, a movie, an event, etc. The heavy duty Vday test is just way too much pressure and won't prove anything.

I’ve come to the realization that if I wait for him to ask me out, I’ll be waiting forever...I figured that if I ask him to spend Valentine’s Day with me, he’ll figure out that I’m interested.

[dias]

Making the first move is easy. Only the first 100 times are difficult. Don't worry

 

Kidding aside, my opinion is to just ask him point blank if he likes you and if he wants a relationship with you. Sometimes the direct approach is the best, notably when you have been hanging out for so long!

[panther]

He has asked you out twice, though not on dates really so we can't tell here if he would be interested in dating you.

As you said, the worst thing that can happen is a polite "no" or excuse and you will get over it if that happens. But do ask him out for coffee or dinner, as long as it's only the two of you so hopefully he gets that it's a date because any other thing like going to a party together is much more casual an can be interpreted either way.

[DancingFool]

Agree that asking him to dinner for v-day and then hoping he will figure it out and if not, then getting into some confession about your feelings is really way too complicated, too much pressure and too much drama.

 

Keep it simple and just ask him directly and plainly if he would be interested in dating you. This kind of a yes or no situation will actually be a lot less awkward and painful for the both of you, especially if he politely declines. It will leave you room to remain friends...if you can be just friends with him that is..... Confessions are inherently dramatic and make things very awkward. If I were you, I'd avoid that and keep things more simple and straightforward because in the end it will be less painful for you.

[amazingcuzitis]

It may be best to simply invite him to come for dinner, or go for coffee, a movie, an event, etc. The heavy duty Vday test is just way too much pressure and won't prove anything.

 

I’ve asked him out to coffee and dinner and things like that many times, and we’ve always had fun but I can never tell if he thinks it’s a date or if it’s just as friends. My line of thinking is that we’re friends, and we’re both going to spend V Day alone if I don’t ask him to hang out, so if nothing else it might just be nice to spend the day in the company of a friend, rather than alone in an empty apartment. I know him pretty well and I don’t think he would interpret the situation as being too much pressure or too much drama. And, I’m not planning on taking him to a romantic restaurant or anything grand, I was just thinking we’d do some of the usual things that we do together

[reinventmyself]

7 weeks between now and V day.

Surely you will see him before then. Have you initiated any physical contact with, taken his arm, hugged or ever tried to kiss him?

You can do that, you know. You don't always have to wait for the man to make the first move. Especially when he's shy.

[amazingcuzitis]

7 weeks between now and V day.

Surely you will see him before then. Have you initiated any physical contact with, taken his arm, hugged or ever tried to kiss him?

You can do that, you know. You don't always have to wait for the man to make the first move. Especially when he's shy.

 

I’ve hugged him, a lot. But I could never try to kiss him lolololol. When it comes to expressing my feelings, I’m much better at doing it verbally than physically. I know I would make a fool of myself if my first move was physical

[reinventmyself]

I’ve hugged him, a lot. But I could never try to kiss him lolololol. When it comes to expressing my feelings, I’m much better at doing it verbally than physically. I know I would make a fool of myself if my first move was physical

Not necessarily.

Do you get the impression he'd like to kiss you but it too nervous too?

I've made the first move more than once. They appreciated it. Your guy may too.

[abitbroken]

alked deep into the night and he brought up the topic of previous relationships, and we both shared our emotional scars and our hopes for the future.

 

if he's shy and doesn't seem like the guy who spills his guts to everyone, i'd say that could be a green light on his part. What were your hopes for the future? His? I think you need to take the bull by the horns and do something datey and its your turn to give him the green light. He took you as a plus one, he started to talk about his relationship past and keeps asking you out. I think you SHOULD make a physical move - it could be as simple as gently reaching for his hand across the table, etc. You don't have to grab him and stick your tongue down his throat.

 

btw, did he call you and go anywhere with you after that revelation?

[JaggerJim]

I think if he liked you, he would have made a move on you already. You could be in the friend-zone. Are you going to be ok with that, if that's the case?

[abitbroken]

I think if he liked you, he would have made a move on you already. You could be in the friend-zone. Are you going to be ok with that, if that's the case?

 

Thing is -- with sexual harrassment and "consent" in the news so heavily these days, I think a lot of guys are afraid to make a move without the woman really green lighting with it. I would not wait for him to try to kiss her to know if he is interested. He has given enough signs that it could go either way - he keeps asking her out -so i am thinking she needs to give him the green light. They have gone out a lot together and its time for her to give a hint of her own. she has nothing to lose -- because if it turns out he isn't interested, she can move on to someone who is - but he could also be interested and she is being dense about it, as well

[Wiseman2]

If a guy's not in a relationship, vday is just 14 Feb, nothing more so he may not pick up on your "hint". Does he ever ask you out on real dates?

I’ve asked him out to coffee and dinner and things like that many times, and we’ve always had fun but I can never tell if he thinks it’s a date or if it’s just as friends.

[PICCOLLO]

Sounds like you guys are dating.

 

Its pretty rare for a guy to friendzone a girl (ie. friends without benefits) unless he has a girlfriend. You’ve established that you are both quite shy.

 

Have you guys been drunk together? That generally settles the nerves.

 

I guess you have to ask yourself if you’d be happy for things to stay as they are. If yes, then do nothing. If no, then ask him to dinner and kiss him!

[Pleasedonot5]

I say you go with your strengths and make it verbal. I've always found surprise kisses weird. You should get a cue before going for a kiss (i.e. a moment of tension, eye contact, looking at each other's lips, etc.). Maybe verbally is the way to go for you.

 

That said. Vday is too much. Talk before then.