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All was fine until I went on a break with my boyfriend a couple months ago. During this time Scott started flirting with me, and he ended up kissing me. He never told me how he really felt about me and would instead just flirt or deflect. When I finally mustered up the courage to ask him what he wanted, it seemed like he panicked and said “let’s just be friends.” Well, I was fine with that, and then the next day he kissed me again, leaving me very confused. I got back together with my boyfriend, and Scott was respective and stopped kissing me even though we didn’t really have a conversation about it.
We went back to normal friends and everything was fine again until I broke up with my boyfriend. It happened right before I came home from college (I live several states away from my college and even more states away from Scott). Right before we left, Scott kissed me again. Then we each went home and he started flirting a lot with me. However, he’d flirt with me and tell me he wanted to kiss me or things like that, and then he’d talk to me about other girls. He would talk about this one girl that he wanted to date while he would talk about wanting to be with me. Now he’s telling me he doesn’t want to be with that girl anymore and has started more serious flirting with me (even trying to get me a plane ticket to go see him).
Here’s the other issue: He’s a virgin and I’m not. I know he’s been hurt in the past because girls pressure him to have sex, and while I’m not like this, I think he’s nervous that I will be. However, he’s also made numerous comments about wanting to have sex with me, including telling me that if there was one person on campus he’d lose his virginity to, it would be me (said before we had even kissed!!).
So here’s my problem: I really like this guy, as a friend or maybe more but I’m not sure, because I don’t know how he really feels about me; however, I love being around him both as friends and when we were “together” (kissing). I don’t know what to do—if I wait to see if he finally fesses up his feelings for me or if I just forget about it. I don’t want to lose him as a friend, and I’m fine with any relationship he wants (friends, dating, FWB, etc.), but I’m nervous to ask him what he wants because of last time. What should I do? — Not Sure What He Wants
Well, first of all, you need to get some agency in this situation. You’ve been almost entirely passive; everything is about what Scott does (he flirts with you, he kisses you), what Scott says (he talks about other girls, he’s made numerous comments about wanting to have sex with you and how he’d choose you over everyone else to lose his virginity to), and about guessing what Scott wants (“friends, dating, FWB, etc.”) and you’re just “fine” with it all (your words). Girl, no. Have some self-respect. This guy you’ve been platonic friends with kisses you twice and tells you multiple times he wants to have sex with you, but when you ask him what he wants, he says “let’s just be friends” and goes on to talk about other girls? That’s not just confusing and vague and WEIRD, it’s fucking rude. You shouldn’t put up with it.
You say Scott is respectful of you, but this isn’t what respect looks like. This isn’t what friendship looks like. Friends don’t talk about having sex with you and then kiss you (more than once!) and then, when you call them on it and ask them about their feelings, panic and say “let’s just be friends” while continuing to flirt with you aggressively. This is some manipulative bullshit from an immature, inexperienced guy who seemingly not only lacks self-confidence, but also likely doesn’t have much respect for women either. You shouldn’t put up with it, and you sure as shit shouldn’t be willing to do whatever it is he wants — “friends, dating, FWB, etc.” if only he would communicate what it is he wants. Don’t be willing to do whatever a guy wants. Have some boundaries. Be willing to do what YOU want, with maybe a little wiggle room for compromise in certain situations IF your boundaries are respected.
You say you aren’t sure whether you like this guy more than friends because you aren’t sure how he feels. Your feelings are YOURS and they are not dependent on someone else’s. You are your own person – a person who has her own thoughts and opinions. What do YOU want? Are you interested in dating Scott? Then you should say so to him. Tell him that, with all his flirting and the kissing, you thought there might be a chance the interest was mutual and so you want to know if that’s the case and if he wants to try dating. If he says yes, give it a try, but if he says no, tell him the flirting and the kissing has to stop because it’s confusing for you. I would not advise being his FWB unless you like the idea of a no-strings-attached relationship with someone who’s wishy-washy with you, talks about other women with you, and has zero sexual experience. And if those things are a turn-on for you, then I guess Scott is a good fit for you! Regardless, it is beyond time for you to decide what YOU want and to communicate that with Scott since waiting for him to communicate with you is a fruitless endeavor.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.